Taylor-Chicago1

A woman enjoying a summer day on the Chicago Riverwalk.

Known as the Windy City, Chicago in the summer is like no other! Suppose you’re pondering where to vacation in the United States during summertime. In that case, Chicago has everything, from its 24 beaches and numerous rooftop bars along Lake Michigan to its stunning Riverwalk, thriving music festivals and vibrant culinary scene.

Chicago, Illinois is situated on 234 square miles along Lake Michigan. It’s considered the third-largest city in America behind New York City and Los Angeles and boasts the second-largest public transport system in the nation. In fact, it’s known to be the USA’s railroad capital!

A woman at the Willis Tower Skydeck.

The first time I visited the city of Chicago was in April 2017 for a work trip, but it wasn’t until August 2022 that I fully got to experience what this incredible city has to offer! I enjoyed many fun summer activities in Chicago with Mariam of Wandering with Mariam. We explored Chicago’s foodie scene, visited famous landmarks, walked along the Riverwalk and more.

This article is a first-time visitor’s guide to Chicago in the summer. Discover the best things to do in Chicago’s summer months for a great time!

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like. During my time in Chicago, Blueground hosted me in one of their apartments for three nights.


Pin the Below Image to Keep Handy

Chicago in the summer!

Chicago in the Summer Weather:

A woman enjoying a vacation to Chicago, Illinois.

Even though Chicago in the winter months is brutal with harsh, cold temperatures, the summer months are stunning! Temperatures range from highs in the upper 70s°F to lows in the lower 60s°F in June; highs in the lower 80s°F to lows in the high 60s°F in July and highs in the lower 80s°F to lows in the high 60s°F in August.

Lake Michigan plays a massive role in Chicago’s weather and climate during the summer. If winds come in from the east, the temperatures in the city will be cooler, especially along the water. The Windy City does experience many heat waves and you may also get temperatures in the triple digits in July and August!

The hottest month in Chicago is July, with temperatures averaging in the lower 80s° and the wettest month is June, with an average rainfall of 4 inches. Chicago summers also experience a mix of dry and humid weather, but you can expect a decent amount of sun in July and August!

Traveling to and Around Chicago in Summer:

The Chicago Riverwalk in the warmer months.

Getting to Chicago, Illinois, from anywhere in the United States is easy since it’s such a large city. I flew directly from Newark Airport in New Jersey to Chicago O’Hare International Airport. You can find affordable flights through Skyscanner!

You do not need to rent a car to get around the city of Chicago because the public transportation system is incredible. However, you must pick up a rental car if you plan to travel around Illinois and the surrounding states!

Mariam and I mainly got around by walking, taking public transportation and using ridesharing apps. A great way to get from the airport to downtown Chicago is through Go Airport Shuttle!

Chicago is a walk-friendly city; you will want to enjoy the beautiful weather in the summer. However, you can utilize the CTA (Chicago Transit Authority) if you’re going somewhere further that requires transportation. It’s a fast and cost-effective way to get around the city.  

The L is an underground and overground train that takes passengers around Chicago. Click here for the latest fares, travel alerts and city planners and guides. Chicago is also a bike-friendly city and you can also rent one to get around. Travelers can enjoy the half-day bike rentals at Bike and Roll, which has locations at Navy Pier and Millennium Park.

Additionally, the Metra System train services Chicago’s suburban communities and takes locals and visitors to and from the city to the South Shore, the University of Chicago and other surrounding areas.

Additionally, Park City makes for a great stop on a USA road trip! Click here if you are planning to road trip around the United States and want to rent an RV.

Where to Stay during a Chicago Summer:

A woman staying at a Blueground apartment in Chicago.

As a travel blogger, I can live anywhere in the world. With the rise in digital nomads and people working from home, Blueground allows people, like me, who are self-employed, digital nomads or remote workers, to travel slower, live in different cities and experience life like a local.

During my time in the Windy City in the summer of 2022, I had the experience of living like an authentic Chicago local in a Blueground apartment in the heart of the city. My apartment was steps away from the famous Riverwalk and it was also in close walking distance to Millennium Park, Navy Pier and all of Chicago’s best restaurants.

Blueground offers fully furnished homes and flexible leases for digital nomads and remote workers. They are on four continents, in 15 countries and 26 cities, with almost 9,000 apartments to choose from!

Each curated Blueground apartment features modern and premium amenities, from having access to rooftop pools to offering special discounts on gourmet meals and fitness classes. In addition, Blueground takes the stress off guests by doing all the legwork. It is truly a seamless experience!

13 Best Things to do in Chicago in the Summer for First Timers

A woman enjoying a summer trip to Chicago, Illinois.

Summer in Chicago is the best and there are plenty of amazing things to do in the warmer months, from attending festivals to rooftop bar hopping. Below is the best stuff to do in the summer:

Get a Taste of Chicago by Visiting the Best Restaurants:

Chicago ranks as the top foodie city in the Midwest and one of the best in the United States! During your first trip to Chicago, you must visit the below restaurants. Each place did not disappoint!

Enjoying a lunch outdoors at Bar Mar by José Andres in Chicago in the summer.

Bar Mar by José Andrés: The number one restaurant I visited during my Chicago summer trip was Bar Mar by José Andrés. It’s a sophisticated restaurant that specializes in tapas. This stunning spot lets you enjoy fresh seafood, Spanish classics and festive cocktails.

Mariam and I came to Bar Mar for lunch and shared the Neptune’s Pillows, which included sesame rocoto, spicy tuna and fresh wasabi; tuna ceviche Nikkei that had big eye tuna, soy-cured egg yolk, ponzu, puffed quinoa, avocado, jicama, red onion and furikake; pan con tomate and chicken croquettes with sangria. Everything was delicious!

Bar Mar is in the Chicago Loop and faces the Chicago River. There is both indoor and outdoor seating to enjoy during summertime.

Greek Desserts

Ēma: Situated in Chicago’s River North is Ēma, a swanky Mediterranean restaurant. It’s known for its delicious dips, spreads, cocktails and mezze, which are Mediterranean small plates. It is a great place to visit in Chicago in the summer due to its light and flavorful cuisine and outdoor seating!

I loved how beautiful this restaurant was with its décor, stringed lights and welcoming ambiance. During our evening at Ēma, Mariam and I shared the toasted almond and garlic spread with freshly baked pita bread. I enjoyed Brussels sprouts with crispy shallots, pumpkin seeds and sherry glaze and Mariam had the spicy toothpick lamb that included cumin, chilies and house yogurt.

I savored the grilled octopus with fingerlings and preserved lemon vinaigrette for my main meal with the Slow Cheetah Mezcal. Mariam had the lamb and beef kefta, including lemon, olive oil, tzatziki and jasmine rice, with the Pomegranate Backsplash Mocktail. The desserts we shared were a honey pie, frozen Greek yogurt with olive oil and sea salt as well as a sticky date cake with Medjool dates, sumac, whiskey caramel and whipped cream.

French-Vietnamese dinner from Le Colonial in Chicago.

Le Colonial: Situated off the Magnificent Mile in the Near North Side of Chicago is Le Colonial, an upscale French Vietnamese fusion restaurant. It celebrates the spirit and flavors of Saigon, Vietnam in the 1920s.

At Le Colonial, we savored the Ga Xao Xa Ot, which is the spicy chicken stir-fry, Chao Tom, which is shrimp on sugar cane and garlic noodles. I also got the spicy margarita!

Other best restaurants in Chicago:

For all the foodies, one of the best things to do in Chicago in June is to make your way to the Chicago Food Truck Festival! It’s one of America’s largest events for gourmet food trucks. You can enjoy baked goods, delicious Mexican cuisine, Asian fusion, seafood, Soul food and more!

Chicago also boasts a great Little Italy neighborhood and Chinatown, which hold a lot of fantastic restaurants, cafés, markets, food stands and more! You will not be disappointed if you visit either of these neighborhoods.

One of my favorite places to stop in Chicago is Garrett Popcorn Shops. There are locations all around the city and it’s one of the best places to get souvenirs for loved ones back home! You can enjoy various flavored popcorn at Garrett Popcorn Shops, from caramel to Buffalo ranch.

Enjoy a Chicago Coffee Shop in the Morning:

A woman enjoying a morning at Sawada Coffee.

In addition to its excellent restaurants, Chicago has great coffee shops to enjoy in the morning or the afternoon for a pick-me-up!

There are many different coffee shops, cafés and bakeries to enjoy around the city. Below is where Mariam and I visited during our summer trip to Chicago!

Coffee from Sawada Coffee in Chicago.

Sawada Coffee: One of my favorite coffee shops in Chicago is Sawada Coffee in the West Loop. It’s located in an industrial, hipster space with stringed lights, a courtyard and plenty of space to get work done. It’s the perfect place for digital nomads. Sawada Coffee also has craft beer and live music at night.

You can enjoy specialty coffee drinks at Sawada Coffee, including their incredible dark roasts, matcha, and baked goods like croissants, donuts, banana bread, cookies/brownies, etc.

A Bamboloni from Bambobar in Chicago, Illinois.

BomboBar: Also located in Chicago’s West Loop, in the Fulton Market neighborhood is BomboBar. You can enjoy great coffee here, and this spot is known for its bomboloni, a hole-less Italian donut.

At BomboBar, you can appreciate a classic bomboloni or have them in a mini form. There are a variety of dipping sauces to choose from at BomboBar, such as chocolate hazelnut, vanilla crème Anglaise, salted caramel and peanut butter and jelly strawberry, which is what I had!

BomboBar also sells different gelato flavors, shakes and sorbetto, such as strawberry cheesecake, cookies & cream and berry & mango.

A croissant from Goddess and the Baker in Chicago.

Goddess and the Baker: Another great coffee shop and bakery in Chicago, with multiple locations, is Goddess and the Baker. Mariam and I visited the River North location, but you can also visit the bakeries in Millennium Park, the Loop, on the Riverfront, Wells & Superior and Brookfield, Wisconsin.

Goddess and the Baker is a great spot for breakfast and lunch in Chicago, as it offers a variety of specialty lattes, baked goods, salads, soups and sandwiches. It also boasts an all-day breakfast menu where you can savor omelets, breakfast sandwiches and burritos, bagels, oatmeals and more.

Stroll the Chicago Riverwalk during the Summer:

The Chicago Riverwalk in the summer.

If you’re wondering what to do in Chicago in the summer to stay active, you must walk along the Chicago Riverwalk and admire the city’s iconic buildings and architecture.

The Chicago Riverwalk is a scenic promenade in the heart of the city that includes walking paths, restaurants and bars, benches and theater seating, public art displays, outdoor summer activities, boat tours and more. It also holds the Vietnam Veterans Memorial Plaza.

The Chicago Riverwalk at night.

Along the Riverwalk are stunning bridges and two of the most iconic buildings to admire are the Wrigley Building and the Marina Towers, which are apartments considered “Corn Cob Towers” due to their unique design. (You can see the Marina Towers in the photo above.)

One of the best Chicago summer activities is renting kayaks from Urban Kayaks and enjoying a guided river tour. During this incredible experience, you can paddle under historic bridges and get a history lesson. You can even do this tour during sunset or while the fireworks go off at night. It’s a lot of fun!

Another wonderful thing to do in Chicago during the summer season is to enjoy the Chicago Architecture Foundation Center River Cruise, where you’ll sail aboard with Chicago’s First Lady Cruises. On this boat cruise, you’ll learn about the architectural style of Chicago’s most famous and historic buildings and landmarks. You will also listen to stories of the people who established the city! It’s a 90-minute tour and includes a full-service bar.

An excellent place to relax and catch up with friends is City Winery. With locations around the country, City Winery is a beautiful waterfront venue that includes a winery, restaurant and live music space.

See the Cloud Gate at Millennium Park and Enjoy Grant Park:

A woman at the Cloud Gate in Chicago in the summer.

The Chicago Park District is a prime spot during summer in Chicago! It’s home to Grand Park, which boasts the famous Millennium Park, renowned for the Cloud Gate, or “The Bean.”

The Cloud Gate is an iconic mirrored archway created by artist Anish Kapoor. It’s one of the top photo spots in Chicago, as the structure provides unique reflections for selfies. If you want to see the Cloud Gate without crowds, you must visit early in the morning as it’s one of the most packed spots in the city.

Another great thing to do in Chicago in the summer is to walk through Lurie Garden in the park. It’s where you can admire stunning flowers, bird watch and even take free tours to learn more.

Also located in Grant Park is Maggie Daley Park, which offers many fun summer activities in Chicago! You can enjoy rock wall climbing, mini golf, roller skating, tennis, a picnic and more. There is also a children’s playground at this fun park.

Grant Park is considered the best place to catch free music concerts and free outdoor movies during a Chicago summer! In the Millennium Park section, the Jay Pritzker Pavilion is where the Chicago Blues Festival, Chicago Jazz Festival and the outdoor classical music series occur. Since there are a lot of green spaces in the park, you can bring lawn chairs and blankets and enjoy talented worldwide musicians and local music artists perform.

During the warmer months, you can also find food trucks scattered throughout Grant Park. There is no better time to spend in this park than in summer. In this lovely area, you can also find Buckingham Fountain, the Art Institute of Chicago and the Museum Campus!

Savor the Best Chicago Deep-Dish Pizza:

Deep-dish pizza.

Undoubtedly, one of my favorite things in Chicago is to savor deep-dish pizza! No matter what time of the year you decide to travel to Chicago, there is always a perfect time to savor this tasty Windy City staple!

What makes Chicago pizza unique from others is that the dough is pressed to the sides of a pan, making it like an apple pie. It is then filled with chunky tomato sauce, usually spicy, and is topped with a thick layer of cheese and toppings.

Deep-dish pizza came to Chicago in 1943. Neapolitan immigrants Sewell and Riccardo opened the doors to Pizzeria Uno. Later, Adolpho Malnati, a former employee of Pizzeria Uno, claimed he was the one who invented Chicago’s famous deep-dish pizza. In 1971, his son Lou Malnati opened his own pizzeria in Chicago.

Nowadays, Pizzeria Uno and Lou Malnati’s are chain restaurants and have locations throughout the United States. Other famous Chicago pizzerias are Giordano’s and Pequod’s.

During my first trip to Chicago for work, I ate at Giordano’s and wasn’t impressed, so when I returned during the summer of 2022, I was told to eat at Pequod’s and enjoyed it more.

If you’re visiting Chicago this summer, it’s nevertheless a must to try the deep-dish pizza! There are a lot of great toppings you can add and it’s fun to eat.

Pequod’s Pizza is in Lincoln Park. After your deep-dish lunch, you can head to the Lincoln Park Zoo or North Avenue Beach, also in the area!

Admire Chicago Skyline Views at the Willis Tower:

A woman at the Skydeck at the Willis Tower.

The Willis Tower once called the Sears Tower, is an icon of Chicago’s skyline! At 1,454 feet, the Willis Tower was once the world’s tallest building until 1998, when the Petronas Towers in Kuala Lumpur, Malaysia surpassed it by 33 feet.

Later on, One World Trade Center in New York City surpassed both and nowadays, the tallest building in the world is the Burj Khalifa in Dubai at 2,722 feet.

Even though many buildings have surpassed the Willis Tower in height, visiting it is still the best way to enjoy Chicago’s skyline views in the summer!  A fun fact about the Willis Tower is that it sways 6 inches on a windy day.

When you first enter the Willis Tower, you will walk through an exhibit that takes you through Chicago’s history and culture. Once you take the elevator to the Skydeck, you can enjoy incredible views of the Chicago skyline and Lake Michigan from the many ledges.

Please note that there is a long line to enter one of the ledges and you only have a minute to enjoy the views and take photos. Don’t worry though, the line goes quickly and you can always hop back on to get more pictures and videos.

Watch a Chicago Broadway Show:

Chicago Theater

Just like New York City, Broadway is also important in Chicago. During your first trip to the Windy City, you must see a Broadway show!

Even in the summer, Broadway thrives in the city and seeing a show is one of the best things to do on a rainy day in Chicago! Some of the leading shows you can see during your trip are The Tina Turner Musical, The Book of Mormon, Into the Woods and Disney’s Aladdin.

Wander around Navy Pier during a Chicago Summer:

Navy Pier during sunrise.

A Chicago summer vacation is only complete with visiting Navy Pier! Along Lake Michigan, Navy Pier boasts Pier Park, where you and your children can enjoy carnival-like rides and games. One of the most iconic rides at this park is the Centennial Wheel!

Additionally, Navy Pier is where you can enjoy free fireworks on the lake every Wednesday and Saturday night during the summer months.

Other summer fun spots on Navy Pier are the Miller Lite Beer Garden, Chicago Children’s Museum, Offshore Rooftop, plus more!

Relax at North Avenue Beach or Oak Street Beach:

The beaches of Chicago to enjoy during vacation.

One of the best parts about visiting Chicago in the summer is enjoying one of its many beaches! North Avenue Beach is the most popular beach in the Windy City, which boasts large, white sand beaches, fun beach bars, great seafood restaurants and more.

In addition to relaxing at the beach, you can enjoy outdoor summer activities such as paddleboarding, kayaking and jet skiing at this spot! There are also volleyball courts.

Another great Chicago beach to enjoy during a summer day is Oak Street Beach. At this beach, you can see the Chicago skyline from the shoreline and it also includes Whispers at Oak Street Beach, where you can reserve a private cabana!

North Avenue Beach is near the Lincoln Park Zoo and Oak Street Beach is by the Magnificent Mile!

Catch a Chicago Cubs Game at Wrigley Field:

Wrigley Field in Chicago during summer.

Nothing screams summer more than attending a baseball game! The Cubs are Chicago’s official MLB team, and you must get tickets to see a game at the iconic Wrigley Field.

Not only is deep-dish pizza a staple to Chicago, but so are hot dogs! During a Chicago Cubs game, you must get a local beer and Chicago dog while you cheer on your favorite players. A Chicago-style dog is an all-beef frankfurter with a steamed poppy seed bun. It’s usually topped with mustard, relish, onions, tomatoes, kosher pickles and peppers.

Attend Summer Festivals in Chicago:

Lollapalooza in Chicago.

One of the best things to do in Chicago in July and August is to attend music festivals! Below is a list of the popular summer festivals Chicago offers:

  • Lollapalooza (August): This world-famous music festival in Chicago’s Grant Park attracts visitors nationwide. Artists that have performed at Lollapalooza in the past were Ariana Grande, Tame Impala, The Chainsmokers, Childish Gambino and more.
  • Chicago Blues Festival (June): Not only is Chicago the blues capital of the world, but the Chicago Blues Festival is also the largest free blues event in Millennium Park. In the past, the Chicago Blues Festival hosted Ray Charles, Bonnie Raitt and B.B. King, to name a few.
  • Pitchfork Music Festival (July): This three-day indie rock festival takes place in Union Park and draws performers like Run the Jewels, Yeah Yeah Yeahs and Deafheaven.

Other great summer festivals to attend in Chicago are Wicker Park Fest, Chicago Jazz Festival, Pride in the Park and Windy City Smokeout.

Shop Along the Magnificent Mile:

Chicago Riverwalk

Just like New York has 5th Avenue, Los Angeles has Rodeo Drive, Paris has the Champs d’Élysées and London has Oxford Street, you bet Chicago has its own dedicated shopping street.

If you enjoy some retail therapy, you must shop along the Magnificent Mile on North Michigan Avenue! You can find everything from designer clothing stores to pet shops, along with large department stores to flower shops along the Magnificent Mile.


A woman enjoying Chicago in the summer.

Planning a memorable USA trip? Find more USA travel tips here.

Looking for more fun city trips to take this summer? Check out the below:

What to do for Your First Time in San Francisco

2 Fun Days in Portland, Oregon

What to do with One Day in Charlotte, NC

I hope you all enjoyed discovering the best things to do in Chicago in the summer. If you have any questions, please email me at info@browneyedflowerchild.com.

Currency: United States Dollar, Capital: Washington D.C., IL State Capital: Springfield, Time Zone: Central Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Chicago Look:

Click here to shop my Poshmark closet!

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4 Comments

  1. Kim Deer on March 28, 2023 at 10:39 pm

    This is one stunning city on my bucket list to visit ~ Chicago looks so beautiful during the summer season! So much to do and such great restaurants and bars/rooftops. The beaches look gorgeous and the Riverwalk is magical with the beautiful color of the water. Great guide on this fabulous city! Love you, mom 👩🏻 xoxo ♥️

    • Taylor Deer on April 2, 2023 at 7:29 am

      It really is a beautiful city, especially during the summer!

  2. Aalish on May 11, 2024 at 6:06 am

    Chicago is one of my most favorite city. But in summer I have never visit. Coming back from tours from new york. I will enjoy summer vocation in Chicago.

    • Taylor Deer on May 11, 2024 at 4:27 pm

      Chicago truly is special! Since it gets cold quickly, I do believe summer is the best time to visit because of how much there is to do!

Leave a Comment





Taylor-Chicago1

A woman enjoying a summer day on the Chicago Riverwalk.

Known as the Windy City, Chicago in the summer is like no other! Suppose you’re pondering where to vacation in the United States during summertime. In that case, Chicago has everything, from its 24 beaches and numerous rooftop bars along Lake Michigan to its stunning Riverwalk, thriving music festivals and vibrant culinary scene.

Chicago, Illinois is situated on 234 square miles along Lake Michigan. It’s considered the third-largest city in America behind New York City and Los Angeles and boasts the second-largest public transport system in the nation. In fact, it’s known to be the USA’s railroad capital!

A woman at the Willis Tower Skydeck.

The first time I visited the city of Chicago was in April 2017 for a work trip, but it wasn’t until August 2022 that I fully got to experience what this incredible city has to offer! I enjoyed many fun summer activities in Chicago with Mariam of Wandering with Mariam. We explored Chicago’s foodie scene, visited famous landmarks, walked along the Riverwalk and more.

This article is a first-time visitor’s guide to Chicago in the summer. Discover the best things to do in Chicago’s summer months for a great time!

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like. During my time in Chicago, Blueground hosted me in one of their apartments for three nights.


Pin the Below Image to Keep Handy

Chicago in the summer!

Chicago in the Summer Weather:

A woman enjoying a vacation to Chicago, Illinois.

Even though Chicago in the winter months is brutal with harsh, cold temperatures, the summer months are stunning! Temperatures range from highs in the upper 70s°F to lows in the lower 60s°F in June; highs in the lower 80s°F to lows in the high 60s°F in July and highs in the lower 80s°F to lows in the high 60s°F in August.

Lake Michigan plays a massive role in Chicago’s weather and climate during the summer. If winds come in from the east, the temperatures in the city will be cooler, especially along the water. The Windy City does experience many heat waves and you may also get temperatures in the triple digits in July and August!

The hottest month in Chicago is July, with temperatures averaging in the lower 80s° and the wettest month is June, with an average rainfall of 4 inches. Chicago summers also experience a mix of dry and humid weather, but you can expect a decent amount of sun in July and August!

Traveling to and Around Chicago in Summer:

The Chicago Riverwalk in the warmer months.

Getting to Chicago, Illinois, from anywhere in the United States is easy since it’s such a large city. I flew directly from Newark Airport in New Jersey to Chicago O’Hare International Airport. You can find affordable flights through Skyscanner!

You do not need to rent a car to get around the city of Chicago because the public transportation system is incredible. However, you must pick up a rental car if you plan to travel around Illinois and the surrounding states!

Mariam and I mainly got around by walking, taking public transportation and using ridesharing apps. A great way to get from the airport to downtown Chicago is through Go Airport Shuttle!

Chicago is a walk-friendly city; you will want to enjoy the beautiful weather in the summer. However, you can utilize the CTA (Chicago Transit Authority) if you’re going somewhere further that requires transportation. It’s a fast and cost-effective way to get around the city.  

The L is an underground and overground train that takes passengers around Chicago. Click here for the latest fares, travel alerts and city planners and guides. Chicago is also a bike-friendly city and you can also rent one to get around. Travelers can enjoy the half-day bike rentals at Bike and Roll, which has locations at Navy Pier and Millennium Park.

Additionally, the Metra System train services Chicago’s suburban communities and takes locals and visitors to and from the city to the South Shore, the University of Chicago and other surrounding areas.

Additionally, Park City makes for a great stop on a USA road trip! Click here if you are planning to road trip around the United States and want to rent an RV.

Where to Stay during a Chicago Summer:

A woman staying at a Blueground apartment in Chicago.

As a travel blogger, I can live anywhere in the world. With the rise in digital nomads and people working from home, Blueground allows people, like me, who are self-employed, digital nomads or remote workers, to travel slower, live in different cities and experience life like a local.

During my time in the Windy City in the summer of 2022, I had the experience of living like an authentic Chicago local in a Blueground apartment in the heart of the city. My apartment was steps away from the famous Riverwalk and it was also in close walking distance to Millennium Park, Navy Pier and all of Chicago’s best restaurants.

Blueground offers fully furnished homes and flexible leases for digital nomads and remote workers. They are on four continents, in 15 countries and 26 cities, with almost 9,000 apartments to choose from!

Each curated Blueground apartment features modern and premium amenities, from having access to rooftop pools to offering special discounts on gourmet meals and fitness classes. In addition, Blueground takes the stress off guests by doing all the legwork. It is truly a seamless experience!

13 Best Things to do in Chicago in the Summer for First Timers

A woman enjoying a summer trip to Chicago, Illinois.

Summer in Chicago is the best and there are plenty of amazing things to do in the warmer months, from attending festivals to rooftop bar hopping. Below is the best stuff to do in the summer:

Get a Taste of Chicago by Visiting the Best Restaurants:

Chicago ranks as the top foodie city in the Midwest and one of the best in the United States! During your first trip to Chicago, you must visit the below restaurants. Each place did not disappoint!

Enjoying a lunch outdoors at Bar Mar by José Andres in Chicago in the summer.

Bar Mar by José Andrés: The number one restaurant I visited during my Chicago summer trip was Bar Mar by José Andrés. It’s a sophisticated restaurant that specializes in tapas. This stunning spot lets you enjoy fresh seafood, Spanish classics and festive cocktails.

Mariam and I came to Bar Mar for lunch and shared the Neptune’s Pillows, which included sesame rocoto, spicy tuna and fresh wasabi; tuna ceviche Nikkei that had big eye tuna, soy-cured egg yolk, ponzu, puffed quinoa, avocado, jicama, red onion and furikake; pan con tomate and chicken croquettes with sangria. Everything was delicious!

Bar Mar is in the Chicago Loop and faces the Chicago River. There is both indoor and outdoor seating to enjoy during summertime.

Greek Desserts

Ēma: Situated in Chicago’s River North is Ēma, a swanky Mediterranean restaurant. It’s known for its delicious dips, spreads, cocktails and mezze, which are Mediterranean small plates. It is a great place to visit in Chicago in the summer due to its light and flavorful cuisine and outdoor seating!

I loved how beautiful this restaurant was with its décor, stringed lights and welcoming ambiance. During our evening at Ēma, Mariam and I shared the toasted almond and garlic spread with freshly baked pita bread. I enjoyed Brussels sprouts with crispy shallots, pumpkin seeds and sherry glaze and Mariam had the spicy toothpick lamb that included cumin, chilies and house yogurt.

I savored the grilled octopus with fingerlings and preserved lemon vinaigrette for my main meal with the Slow Cheetah Mezcal. Mariam had the lamb and beef kefta, including lemon, olive oil, tzatziki and jasmine rice, with the Pomegranate Backsplash Mocktail. The desserts we shared were a honey pie, frozen Greek yogurt with olive oil and sea salt as well as a sticky date cake with Medjool dates, sumac, whiskey caramel and whipped cream.

French-Vietnamese dinner from Le Colonial in Chicago.

Le Colonial: Situated off the Magnificent Mile in the Near North Side of Chicago is Le Colonial, an upscale French Vietnamese fusion restaurant. It celebrates the spirit and flavors of Saigon, Vietnam in the 1920s.

At Le Colonial, we savored the Ga Xao Xa Ot, which is the spicy chicken stir-fry, Chao Tom, which is shrimp on sugar cane and garlic noodles. I also got the spicy margarita!

Other best restaurants in Chicago:

For all the foodies, one of the best things to do in Chicago in June is to make your way to the Chicago Food Truck Festival! It’s one of America’s largest events for gourmet food trucks. You can enjoy baked goods, delicious Mexican cuisine, Asian fusion, seafood, Soul food and more!

Chicago also boasts a great Little Italy neighborhood and Chinatown, which hold a lot of fantastic restaurants, cafés, markets, food stands and more! You will not be disappointed if you visit either of these neighborhoods.

One of my favorite places to stop in Chicago is Garrett Popcorn Shops. There are locations all around the city and it’s one of the best places to get souvenirs for loved ones back home! You can enjoy various flavored popcorn at Garrett Popcorn Shops, from caramel to Buffalo ranch.

Enjoy a Chicago Coffee Shop in the Morning:

A woman enjoying a morning at Sawada Coffee.

In addition to its excellent restaurants, Chicago has great coffee shops to enjoy in the morning or the afternoon for a pick-me-up!

There are many different coffee shops, cafés and bakeries to enjoy around the city. Below is where Mariam and I visited during our summer trip to Chicago!

Coffee from Sawada Coffee in Chicago.

Sawada Coffee: One of my favorite coffee shops in Chicago is Sawada Coffee in the West Loop. It’s located in an industrial, hipster space with stringed lights, a courtyard and plenty of space to get work done. It’s the perfect place for digital nomads. Sawada Coffee also has craft beer and live music at night.

You can enjoy specialty coffee drinks at Sawada Coffee, including their incredible dark roasts, matcha, and baked goods like croissants, donuts, banana bread, cookies/brownies, etc.

A Bamboloni from Bambobar in Chicago, Illinois.

BomboBar: Also located in Chicago’s West Loop, in the Fulton Market neighborhood is BomboBar. You can enjoy great coffee here, and this spot is known for its bomboloni, a hole-less Italian donut.

At BomboBar, you can appreciate a classic bomboloni or have them in a mini form. There are a variety of dipping sauces to choose from at BomboBar, such as chocolate hazelnut, vanilla crème Anglaise, salted caramel and peanut butter and jelly strawberry, which is what I had!

BomboBar also sells different gelato flavors, shakes and sorbetto, such as strawberry cheesecake, cookies & cream and berry & mango.

A croissant from Goddess and the Baker in Chicago.

Goddess and the Baker: Another great coffee shop and bakery in Chicago, with multiple locations, is Goddess and the Baker. Mariam and I visited the River North location, but you can also visit the bakeries in Millennium Park, the Loop, on the Riverfront, Wells & Superior and Brookfield, Wisconsin.

Goddess and the Baker is a great spot for breakfast and lunch in Chicago, as it offers a variety of specialty lattes, baked goods, salads, soups and sandwiches. It also boasts an all-day breakfast menu where you can savor omelets, breakfast sandwiches and burritos, bagels, oatmeals and more.

Stroll the Chicago Riverwalk during the Summer:

The Chicago Riverwalk in the summer.

If you’re wondering what to do in Chicago in the summer to stay active, you must walk along the Chicago Riverwalk and admire the city’s iconic buildings and architecture.

The Chicago Riverwalk is a scenic promenade in the heart of the city that includes walking paths, restaurants and bars, benches and theater seating, public art displays, outdoor summer activities, boat tours and more. It also holds the Vietnam Veterans Memorial Plaza.

The Chicago Riverwalk at night.

Along the Riverwalk are stunning bridges and two of the most iconic buildings to admire are the Wrigley Building and the Marina Towers, which are apartments considered “Corn Cob Towers” due to their unique design. (You can see the Marina Towers in the photo above.)

One of the best Chicago summer activities is renting kayaks from Urban Kayaks and enjoying a guided river tour. During this incredible experience, you can paddle under historic bridges and get a history lesson. You can even do this tour during sunset or while the fireworks go off at night. It’s a lot of fun!

Another wonderful thing to do in Chicago during the summer season is to enjoy the Chicago Architecture Foundation Center River Cruise, where you’ll sail aboard with Chicago’s First Lady Cruises. On this boat cruise, you’ll learn about the architectural style of Chicago’s most famous and historic buildings and landmarks. You will also listen to stories of the people who established the city! It’s a 90-minute tour and includes a full-service bar.

An excellent place to relax and catch up with friends is City Winery. With locations around the country, City Winery is a beautiful waterfront venue that includes a winery, restaurant and live music space.

See the Cloud Gate at Millennium Park and Enjoy Grant Park:

A woman at the Cloud Gate in Chicago in the summer.

The Chicago Park District is a prime spot during summer in Chicago! It’s home to Grand Park, which boasts the famous Millennium Park, renowned for the Cloud Gate, or “The Bean.”

The Cloud Gate is an iconic mirrored archway created by artist Anish Kapoor. It’s one of the top photo spots in Chicago, as the structure provides unique reflections for selfies. If you want to see the Cloud Gate without crowds, you must visit early in the morning as it’s one of the most packed spots in the city.

Another great thing to do in Chicago in the summer is to walk through Lurie Garden in the park. It’s where you can admire stunning flowers, bird watch and even take free tours to learn more.

Also located in Grant Park is Maggie Daley Park, which offers many fun summer activities in Chicago! You can enjoy rock wall climbing, mini golf, roller skating, tennis, a picnic and more. There is also a children’s playground at this fun park.

Grant Park is considered the best place to catch free music concerts and free outdoor movies during a Chicago summer! In the Millennium Park section, the Jay Pritzker Pavilion is where the Chicago Blues Festival, Chicago Jazz Festival and the outdoor classical music series occur. Since there are a lot of green spaces in the park, you can bring lawn chairs and blankets and enjoy talented worldwide musicians and local music artists perform.

During the warmer months, you can also find food trucks scattered throughout Grant Park. There is no better time to spend in this park than in summer. In this lovely area, you can also find Buckingham Fountain, the Art Institute of Chicago and the Museum Campus!

Savor the Best Chicago Deep-Dish Pizza:

Deep-dish pizza.

Undoubtedly, one of my favorite things in Chicago is to savor deep-dish pizza! No matter what time of the year you decide to travel to Chicago, there is always a perfect time to savor this tasty Windy City staple!

What makes Chicago pizza unique from others is that the dough is pressed to the sides of a pan, making it like an apple pie. It is then filled with chunky tomato sauce, usually spicy, and is topped with a thick layer of cheese and toppings.

Deep-dish pizza came to Chicago in 1943. Neapolitan immigrants Sewell and Riccardo opened the doors to Pizzeria Uno. Later, Adolpho Malnati, a former employee of Pizzeria Uno, claimed he was the one who invented Chicago’s famous deep-dish pizza. In 1971, his son Lou Malnati opened his own pizzeria in Chicago.

Nowadays, Pizzeria Uno and Lou Malnati’s are chain restaurants and have locations throughout the United States. Other famous Chicago pizzerias are Giordano’s and Pequod’s.

During my first trip to Chicago for work, I ate at Giordano’s and wasn’t impressed, so when I returned during the summer of 2022, I was told to eat at Pequod’s and enjoyed it more.

If you’re visiting Chicago this summer, it’s nevertheless a must to try the deep-dish pizza! There are a lot of great toppings you can add and it’s fun to eat.

Pequod’s Pizza is in Lincoln Park. After your deep-dish lunch, you can head to the Lincoln Park Zoo or North Avenue Beach, also in the area!

Admire Chicago Skyline Views at the Willis Tower:

A woman at the Skydeck at the Willis Tower.

The Willis Tower once called the Sears Tower, is an icon of Chicago’s skyline! At 1,454 feet, the Willis Tower was once the world’s tallest building until 1998, when the Petronas Towers in Kuala Lumpur, Malaysia surpassed it by 33 feet.

Later on, One World Trade Center in New York City surpassed both and nowadays, the tallest building in the world is the Burj Khalifa in Dubai at 2,722 feet.

Even though many buildings have surpassed the Willis Tower in height, visiting it is still the best way to enjoy Chicago’s skyline views in the summer!  A fun fact about the Willis Tower is that it sways 6 inches on a windy day.

When you first enter the Willis Tower, you will walk through an exhibit that takes you through Chicago’s history and culture. Once you take the elevator to the Skydeck, you can enjoy incredible views of the Chicago skyline and Lake Michigan from the many ledges.

Please note that there is a long line to enter one of the ledges and you only have a minute to enjoy the views and take photos. Don’t worry though, the line goes quickly and you can always hop back on to get more pictures and videos.

Watch a Chicago Broadway Show:

Chicago Theater

Just like New York City, Broadway is also important in Chicago. During your first trip to the Windy City, you must see a Broadway show!

Even in the summer, Broadway thrives in the city and seeing a show is one of the best things to do on a rainy day in Chicago! Some of the leading shows you can see during your trip are The Tina Turner Musical, The Book of Mormon, Into the Woods and Disney’s Aladdin.

Wander around Navy Pier during a Chicago Summer:

Navy Pier during sunrise.

A Chicago summer vacation is only complete with visiting Navy Pier! Along Lake Michigan, Navy Pier boasts Pier Park, where you and your children can enjoy carnival-like rides and games. One of the most iconic rides at this park is the Centennial Wheel!

Additionally, Navy Pier is where you can enjoy free fireworks on the lake every Wednesday and Saturday night during the summer months.

Other summer fun spots on Navy Pier are the Miller Lite Beer Garden, Chicago Children’s Museum, Offshore Rooftop, plus more!

Relax at North Avenue Beach or Oak Street Beach:

The beaches of Chicago to enjoy during vacation.

One of the best parts about visiting Chicago in the summer is enjoying one of its many beaches! North Avenue Beach is the most popular beach in the Windy City, which boasts large, white sand beaches, fun beach bars, great seafood restaurants and more.

In addition to relaxing at the beach, you can enjoy outdoor summer activities such as paddleboarding, kayaking and jet skiing at this spot! There are also volleyball courts.

Another great Chicago beach to enjoy during a summer day is Oak Street Beach. At this beach, you can see the Chicago skyline from the shoreline and it also includes Whispers at Oak Street Beach, where you can reserve a private cabana!

North Avenue Beach is near the Lincoln Park Zoo and Oak Street Beach is by the Magnificent Mile!

Catch a Chicago Cubs Game at Wrigley Field:

Wrigley Field in Chicago during summer.

Nothing screams summer more than attending a baseball game! The Cubs are Chicago’s official MLB team, and you must get tickets to see a game at the iconic Wrigley Field.

Not only is deep-dish pizza a staple to Chicago, but so are hot dogs! During a Chicago Cubs game, you must get a local beer and Chicago dog while you cheer on your favorite players. A Chicago-style dog is an all-beef frankfurter with a steamed poppy seed bun. It’s usually topped with mustard, relish, onions, tomatoes, kosher pickles and peppers.

Attend Summer Festivals in Chicago:

Lollapalooza in Chicago.

One of the best things to do in Chicago in July and August is to attend music festivals! Below is a list of the popular summer festivals Chicago offers:

  • Lollapalooza (August): This world-famous music festival in Chicago’s Grant Park attracts visitors nationwide. Artists that have performed at Lollapalooza in the past were Ariana Grande, Tame Impala, The Chainsmokers, Childish Gambino and more.
  • Chicago Blues Festival (June): Not only is Chicago the blues capital of the world, but the Chicago Blues Festival is also the largest free blues event in Millennium Park. In the past, the Chicago Blues Festival hosted Ray Charles, Bonnie Raitt and B.B. King, to name a few.
  • Pitchfork Music Festival (July): This three-day indie rock festival takes place in Union Park and draws performers like Run the Jewels, Yeah Yeah Yeahs and Deafheaven.

Other great summer festivals to attend in Chicago are Wicker Park Fest, Chicago Jazz Festival, Pride in the Park and Windy City Smokeout.

Shop Along the Magnificent Mile:

Chicago Riverwalk

Just like New York has 5th Avenue, Los Angeles has Rodeo Drive, Paris has the Champs d’Élysées and London has Oxford Street, you bet Chicago has its own dedicated shopping street.

If you enjoy some retail therapy, you must shop along the Magnificent Mile on North Michigan Avenue! You can find everything from designer clothing stores to pet shops, along with large department stores to flower shops along the Magnificent Mile.


A woman enjoying Chicago in the summer.

Planning a memorable USA trip? Find more USA travel tips here.

Looking for more fun city trips to take this summer? Check out the below:

What to do for Your First Time in San Francisco

2 Fun Days in Portland, Oregon

What to do with One Day in Charlotte, NC

I hope you all enjoyed discovering the best things to do in Chicago in the summer. If you have any questions, please email me at info@browneyedflowerchild.com.

Currency: United States Dollar, Capital: Washington D.C., IL State Capital: Springfield, Time Zone: Central Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

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4 Comments

  1. Kim Deer on March 28, 2023 at 10:39 pm

    This is one stunning city on my bucket list to visit ~ Chicago looks so beautiful during the summer season! So much to do and such great restaurants and bars/rooftops. The beaches look gorgeous and the Riverwalk is magical with the beautiful color of the water. Great guide on this fabulous city! Love you, mom 👩🏻 xoxo ♥️

    • Taylor Deer on April 2, 2023 at 7:29 am

      It really is a beautiful city, especially during the summer!

  2. Aalish on May 11, 2024 at 6:06 am

    Chicago is one of my most favorite city. But in summer I have never visit. Coming back from tours from new york. I will enjoy summer vocation in Chicago.

    • Taylor Deer on May 11, 2024 at 4:27 pm

      Chicago truly is special! Since it gets cold quickly, I do believe summer is the best time to visit because of how much there is to do!

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