Stuart Forster provides an overview of 10 of the best things to do in Chicago in summer.
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10 Top things to do in Chicago in summer
Chicago is a great city to visit at any time of year. In summer, the metropolis in Illinois offers much to do outdoors, from attending food and music festivals to relaxing on beaches.
Don’t miss opportunities to view the skyline from Navy Pier or to look across the city from the Skydeck Chicago or the 360 Chicago.
Here’s a look at 10 of the best things to do in Chicago in summer:
Learn about Chicago’s architecture during a river cruise
Chicago Architecture Center engagingly conveys the city’s redevelopment following the fire of 1871, which destroyed more than 17,400 buildings. The Great Chicago Fire left thousands of people homeless and created the necessity to rebuild. That enabled state-of-the-art materials and designs to be utilised. The Home Insurance Building, recognised as the world’s first skyscraper, was completed in 1884.
Guides affiliated with the centre tell the story of Chicago’s architectural heritage from boats that cruise the Chicago River. Even if façades and factoids aren’t your thing, the 90-minute sightseeing cruises are a relaxing way to orientate.
Stroll the Chicago Riverwalk
Not in the mood for a river cruise? Then stroll along the south bank of the Chicago River. The Chicago Riverwalk is 1.25 miles long, running between Lake Michigan and Lake Street. The urban, waterfront park is open to the public between six in the morning and 11 at night.
Head to street level at Michigan Avenue and Wacker Drive, and you’ll see plaques marking the site of Fort Dearborn. Established in 1803, the original fort was destroyed during the War of 1812.
Hiring a kayak is an option if you want to get out on the river.
After exploring the Riverwalk, you’ll be well-placed to head north along the Magnificent Mile. Cross the DuSable Bridge, which features a bust of the city’s founder, Jean Baptiste Point du Sable, to visit shops and restaurants on the Magnificent Mile.
Head to a baseball game
Chicago is the home to two Major League Baseball teams. That means opportunities to attend a game on pretty much any summer day. Both clubs have won the sport’s championship, the World Series, three times.
The Chicago Cubs play at Wrigley Field on the city’s North Side. Tours are a way of exploring the historic stadium, which was built for the Federal League’s Chicago Whales. It became the Cubs’ home in 1916.
The Chicago White Sox play at Rate Field, which opened in 1991, on the South Side. They play in the American League.
Both stadiums have ‘L’ train stations nearby. I found that using public transport on game days helped avoid sitting in traffic.
Appreciate a day of art
Viewing world-class art is ideal on rare days of summer rain or to escape sweltering sunshine. The multi-winged Art Institute of Chicago’s grand main entrance is on Michigan Avenue.
If you’re into art, you’ll find it easy to spend a full day exploring the vast and multifaceted collection. It includes an array of Impressionist and Post-Impressionist works. Grant Wood’s American Gothic and Edward Hopper’s Nighthawks are two of the paintings with ‘must-see’ status. So too is Vincent van Gogh’s The Bedroom.
Like to plan ahead? Book tickets to the Art Institute of Chicago’s temporary exhibitions. In 2026, you can look forward to the likes of Matisse’s Jazz: Rhythms in Color (7 March – 1 June) and Korean National Treasures: 2,000 Years of Art (7 March – 5 July).
Step aboard a German U-boat before heading to the beach
The Griffin Museum of Science and Industry is a family-friendly attraction in Chicago’s Hyde Park district. Fittingly for the Windy City, the Science Storms exhibit provides an opportunity to control a tornado. Visitors can also descend into a coal mine and tour a German submarine captured in 1944.
The museum is a short walk from 57th Street Beach. With golden sands, the beach is lapped by Lake Michigan. It’s an ideal spot to spend a sunny morning or afternoon, either side of exploring exhibits.
Spend a day on the beach
Chicago has several beaches to choose from. North Avenue Beach has golden sand and spectacular skyline views. The pier at North Avenue Beach is an ideal spot for photographing the city’s skyscrapers. If you’re serious about photography, the pier is worth visiting early or late in the day.
You could hire a jet ski and get out on Lake Michigan if you appreciate adventure activities.
If you like to swim, you might want to head further north to Montrose Beach. Popular with families, the beach is near Montrose Point Bird Sanctuary.
Hire a bicycle and explore
Warm sunny days are ideal for getting out on a bike. Chicago is on a plain, meaning the terrain is relatively flat and easy to traverse. Options include riding west to Oak Park to view Frank Lloyd Wright-designed houses. Heading north, via Belmont Rocks, to find a spot on a beach is another.
Day passes are available for Divvy bikes, e-bikes and scooters. The hire and return system is ideal for riding and then exploring attractions. Multiple pick-up and drop locations are dotted around the city.
Other bicycle hire shops are available. Guided sightseeing tours are a way of making the most of the summer weather.
Eat your way around a food festival
Summer in Chicago brings a choice of food festivals. The Chicago Food Truck Festival is held at the South Loop on the weekend of 20-21 June. It’s an opportunity to try a spectrum of culinary offerings.
On the same weekend, Taste of Randolf is held on West Randolf Street. With live music and numerous stalls showcasing aspects of city, The Taste of Randolf begins on Friday, 19 June.
First held in 1980, Taste of Chicago takes place in Grant Park from 8-12 July. It’s reputedly the world’s largest food festival.
Have a laugh at The Second City
The Second City (230 W. N. Avenue) is a long-established comedy club. Enjoy a show while enjoying food and drink served at your seat.
Renowned for its improv shows, The Second City has been the launchpad of numerous successful careers. John Candy, Mike Myers and Tina Fey are among the now internationally renowned comedians who performed.
The Second City has entrances on two streets. So if you order an Uber, make sure that you are at the correct address. I learnt that handy tip the hard way!
Take in a concert at the Grant Park Music Festival
The Grant Park Music Festival features a series of free-to-attend classical music concerts. The 2026 edition runs from 10 June to 15 August. Concerts are held on Wednesday and Friday evenings at the eye-catching Jay Pritzker Pavilion in Millennium Park. Four concerts will also be held at the Harris Theater (205 E. Randolf).
In May, seat reservations open to the general public. I simply turned up and enjoyed a concert. After a day of walking and sightseeing, it proved a lovely way of spending an evening. Some people bring their own folding chairs or blankets, and sit on the grass behind the seating area.
Not a fan of classical music? Maybe the Chicago Blues Festival is more your thing? Also free to attend, the 2026 Chicago Blues Festival is from 4-7 June.
Map of Chicago
Find points of interest in Chicago by zooming in or out of the map below:
Travel to Chicago
British Airways and United Airlines operate direct flights between London Heathrow and Chicago O’Hare International Airport. Icelandair operates a service via its Keflavik hub.
From Manchester, Aer Lingus flies to Chicago via Dublin and KLM via Amsterdam.
Hotels in Chicago
Search for and book accommodation in Chicago using the map below:
Books about Chicago
Interested in art and planning on visiting Chicago? You can buy the following books from Amazon:
DK Top10 Chicago guidebook.
Fodor’s Chicago guidebook.
Lonely Planet Chicago guidebook.
Chicago: A Biography by Dominic A. Pacyga.
Trope Chicago: views of the city by photographers.
Chicago: a novel by Brian Doyle.
Further information
Find more things to do in Chicago by visiting the Choose Chicago website.
Thank you for visiting Go Eat Do and reading this outlining some of the best things to do in Chicago in the summer. The author of the post is Stuart Forster, an award-winning travel writer.
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