12 Fun Things to Do in Chicago During the Summer

There's no other place on Earth quite like Chicago. This unique American city is brimming with history, and its streets are lined with fantastic art exhibits, music venues and tons of attractions — the perfect backdrop to an unforgettable getaway. 

Summer is one of the best times to experience Chicago in full bloom with an unlimited supply of thrilling activities people of all ages will enjoy. Whether you're visiting with friends or hitting the road with your kids, we've put together an awesome list of outings you should definitely add to your Chicago summer vacation itinerary.

1. Kayak the Chicago River

Take in the Windy City's breathtaking skyline by water when you paddle the Chicago River in a kayak. You can rent kayaks with reliable outfitters like Urban Kayaks and Kayak Chicago, which also offer guided tours to help you make the most of your time on the water. 

For a low-key experience, you can go on a three-hour Sunset Paddle offered by Kayak Chicago, where you can watch the sun go down over the city while hanging out with your friends on the calm water. On a beautiful summer day, nothing will beat exploring Chicago on the water and getting some sun.

2. Drink the Best Craft Brews

Chicago is home to over 160 craft breweries, while Illinois has more than 300 microbreweries within its borders — offering an unrivaled selection you won't want to miss out on. Visiting any of the popular breweries, such as Half Acre Brewery Balmoral, Marz Community Brewing and Metropolitan Brewing, is a fantastic summer activity in Chicago. If you're up for a real adventure, you can sign up for Urban Kayak's "Paddle & Pints" tour, as you go on a 90-minute kayaking trip that closes out at one of the nearby pubs for a refreshing drink.

If you want to pair an ice cold glass of beer with some world-class food, Chicago has what you're after — many breweries offer exciting menus. You can also visit in July and experience the Chicago Craft Beer and Pizza Festival that takes place July 20 to 21. Along with offering the chance to taste a sample of more than 70 specialty beers, visitors can also enjoy live music acts in the evening.

 3. Attend a Free Concert at Millenium Park

Chicago has a great music scene, and the free concerts at the Millennium Park Summer Music Series only add to it. You can grab a seat with your friends at the Jap Pritzker Pavilion, or you can bring a blanket or chairs to sit out on the Great Lawn to watch the various musical acts. This summer's music series aims to show a broad spectrum of genre-defying musicians, giving audiences a chance to see established and emerging artists.

Get your groove on every Monday and Thursday between July 1 and August 8. Local, national and international artists from all over will be on display, providing an assortment of toe-tapping music across many genres. On-site concession stands offer food and drink, and Millenium Hall is filled with food options so you can dance the night away with the comfort of a full stomach.

4. Shop at Randolph Street Market Festival

The over 250 vendors at the Randolph Street Market Festival offer a little bit of everything for festival-goers. Art pieces, vintage clothing, housewares, handmade goods, classic furniture and tasty food are all available for your enjoyment. Whether you want to go window shopping to just enjoy the atmosphere or are actually in the market for some vintage furniture, it's almost certain you'll find something unique to look at or buy.

In addition to the incredible shopping you can get done, the festival also offers food and drink options if you need to refuel. If you have young kids, they might not love the idea of going shopping, but they'll love the idea of hunting for treasure in the children's area found in Plumbers Hall, where every child gets a treasure map. With all of the options Randolph Street Market Festival offers, it's well worth the admission price of $12 ($10 if you pay online).

In 2024, the Randolph Street Market Festival is celebrating its 21st anniversary and offering tickets for two events on May 25-26 and September 28-29. 

5. Hit the Beach

Visiting the beach is one of the most overlooked Chicago summer activities. If you aren't from the area, you might not know that Chicago offers 26 lakefront beaches that are perfect to help you cool off. 

There are beaches for every type of beachgoer, whether you want to only listen to the waves crashing at South Shore Beach or experience the bustle of North Avenue Beach. Some areas allow you to bring your furry friend, like Montrose Beach, while others are places where you can swim, sunbathe, play beach volleyball and take in the view. These beaches are only a small sample size of what Chicago has to offer, with museums, cultural centers, and cabanas to be found at other locations. Put on your swimsuit, don't forget your sunscreen, and give the beaches a try!

6. Go on an Architecture Tour Along the Chicago River

Chicago is a city of architectural feats. From the Willis Tower (otherwise known as the Sears Tower to longtime residents) to the Civic Opera House, Chicago's buildings are awe-inspiring and filled with history. If you want to learn more about the city and admire the architectural achievements that went into building it, you should consider scheduling an architecture tour on the weekend.

Wendella Boats provides a 75-minute Chicago River Architecture Tour. On the tour boat, a guide narrates the story of the 130-year history of Chicago's skyline, while bartenders and staff keep guests as comfortable and entertained as possible. Chicago's First Lady also offers their Chicago Architecture Foundation Center River Cruise. This 90-minute cruise is the only river cruise partnered with the Chicago Architecture Center, and it's staffed by passionate volunteers.

7. Go to a Movie at the Park

Over the summer, multiple parks offer free movie showings during the week and on weekends. There's something nostalgic and freeing about seeing a movie outside, and many of Chicago's parks have capitalized on this desire. The Chicago Park District and Gallagher Way offer regular movie nights throughout the summer, showing popular family films like “Wonka,” “Angels in the Outfield,” “Barbie” and many others. 

One of the best parts of catching an outdoor movie is the ability to bring your own food. Pack a blanket and a picnic basket filled with food and drinks to get the most out of your movie experience. Save money and get outside to catch up on all the films you missed by going to a movie at a park this summer.

8. Grab a Drink at Rooftop Bar

If you're planning a night out on the city, consider beginning or ending (or both!) your night at one of the stellar rooftop bars around the city. Not only will you be treated with sophisticated cocktails and a variety of options, but you are also almost guaranteed a breathtaking skyline view.

Another great feature of the rooftop bars is the variety. If you want an intimate spot perfect for a romantic night out, Homestead on the Roof is sure to set the mood and impress. If you're craving some Peruvian street food and Argentine cocktails, Boleo has your back. If you want a place you can hang out with your friends and relax, Streeterville Social is designed for you. Wherever you end up, you'll find a variety of rooftop bars that will fit anyone's style.

9. See a Live Show

Along with all of the other attractions Chicago has to offer, seeing a live show on the weekend is one of the best ways that you could spend your time. Goodman Theater is the largest and oldest not-for-profit theater in Chicago and aims to make programs that contribute to the quality of life in the city. The Chicago Theater delivers high-quality shows across many genres (plays, musicals, comedy acts, classical & opera, etc.). Finally, Broadway in Chicago lets you see, well, Broadway shows in Chicago! The venue rotates theaters and has a variety of shows.

If you want to go to a smaller venue, you should go to one of the five major comedy clubs in the city (Zanies, Laugh Factory, Jokes and Notes, Up Comedy Club and Improv Comedy Club). Along with going to see some standup, comedy fans should also get tickets to an improv show at Second City. The venue helped launch the careers of Steve Carell, Tina Fey and Stephen Colbert (to name a few). Not only can you see improv comedy on stage, but you can also sign up for classes to flex your comedic chops if you are a resident of Chicago and love improv.

10. Visit the Boardwalk at Navy Pier

Navy Pier is Chicago's lakefront treasure and a perfect place to take the whole family. More than just a run-of-the-mill boardwalk, Navy Pier extends six city blocks to make room for the many restaurants, stores, public art pieces and events that the location houses. Some of the most popular places to visit on the peer are the Centennial Wheel (among other rides), the Crystal Gardens and Pok Bros Park.

If you and the family are looking to relax, you can catch the fireworks show that takes place every Wednesday at 9:30 pm and Saturday at 10:15 pm during the summer. Along with the fireworks, you can watch Chicago Shakespeare Theater put on a theatrical production nightly. Want to grab dinner before or after a show? There are tons of restaurant options ranging from seafood to classic Chicago deep dish pizza.

Even better, there is no admission fee to enter Navy Pier. It's open from 10 am to 10 pm on Sunday through Thursday and 10 am to midnight on Friday and Saturday.

11. Cheer for the Cubs or Whitesox

No matter how long you're in town for, catching a baseball game is a must. The Second City is home to two Major League Baseball teams — the Chicago Cubs and the Chicago Whitesox — with the Cubs calling Wrigley Field home since 1916. While the Cubs play on the city's North Side, the White Sox play on the South Side at Guaranteed Rate Field. 

This summertime activity in Chicago is an experience like no other, whether you support the Cubs, Whitesox or another team entirely. Engage in the great American past-time and bring the whole family to a game. There are plenty of food offerings at both venues, and Guaranteed Rate Field even offers the Xfinity Kids Zone to keep younger children entertained.

12. Take a Day Trip to the Volo Auto Museum

If you're searching for an enriching summer pastime in Chicago, consider taking the whole family to the Volo Auto Museum. This family-owned museum is visited by over half a million people a year and consists of more than 60 acres of space, displaying one of the nation's largest collections of modern and classic collector cars. You'll also come up close and personal with various other mechanical marvels, such as boats, trains, planes and more. 

Located just 50 miles north of Chicago, it's one of the best summer activities near the city. It's very accessible, as you can take a day trip via a Metra train ride from the city. When you do visit, plan to spend the whole day exploring over 33 unique exhibits, eating at the on-site pizza parlor and enjoying entertaining guided bus tours. You can also find a self-playing orchestra, Disney gallery and mini-theaters along with many pop culture artifacts around the museum. 

If you want to take advantage of all the other attractions in the local area, you'll want to check out the following warm weather activities in Chicago: 

• Great Wolf Lodge Water Park 
• Six Flags Great America
• Gunree Mills Outlet

Ready to Visit the Chicago Area?

Chicago is a lively city with tons of summertime activities for everyone to take advantage of. At the Volo Auto Museum, we pride ourselves on our Illinois history, dating back to the 1960s. Our location is a must-have on your itinerary, offering a unique way to discover just how special the area is. 

We're open 362 days a year from 10 a.m. to 5 p.m., providing your family with access no matter when you plan your vacation. We're always looking for new ways to add fresh displays and improve on the old ones, ensuring we provide fun for your whole family, no matter the age. Learn more about our auto museum today!