August is here and summer in Chicago is quickly coming to an end. Even though temperatures usually stay warm through early October, there are some things that you can only experience in Chicago during the summer.
Chicago Summer Bucket List
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Looking for bucket list things to do in Chicago this summer? These are the best things to do in Chicago in the summer before it is over.
Watch Free Fireworks at Night
Navy Pier puts on a free fireworks show every Wednesday night (at 9pm) and Saturday night (at 10pm) from Memorial Day weekend through Labor Day weekend.
While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.
Another great option for watching the fireworks is a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.
If you enjoy guided tours, you can also see the fireworks and other attractions on this fireworks segway tour.
Take an Architecture River Cruise
Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise.
Take the Water Taxi to Chinatown
If you do not want to splurge for an architecture river cruise, a cheaper alternative is to hop on a water taxi on the Chicago River.
One of the most water taxi scenic stops is Ping Tom Memorial Park in Chinatown. This beautiful park offers unique views of the Chicago skyline and historic bridges especially at sunset.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is one of the best summer activities in Chicago. Summer is the best season for a lake cruise as the cool breeze on the water is refreshing on a very hot day. While you don’t get to see the buildings up close like you would on a architecture river cruise, you do get to enjoy amazing skyline views especially around sunset.
If your time is short, you can do a combination river and lake cruise.
Have Drinks on the Riverwalk
Chicago Riverwalk is one of the best spots in Chicago for boat and people watching especially in the summer.
Sit down and have a drink at one of its many restaurants and bars. You can enjoy bottomless margaritas every Wednesday and bottomless mimosas every weekend at Island Party Hut on the Riverwalk.
You can see a map of attractions on the Riverwalk here.
Explore the Lakefront
Walk or bike the Lakefront Trail. Walking or biking all or part of the trail is a great way to see the Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.
You can rent a bike through Divvy, the city’s bike sharing program. You can also rent a bike with a helmet for a day or half day here.
Some of the best spots to stop for great skyline views of Chicago include North Avenue Beach, Shedd Aquarium and Promontory Point.
Spend Time at the Beach
Take a dip in the water and enjoy one of Chicago’s many beaches. You can also jump off the concrete into the cool water from the Ledge (or Concrete Beach).
You can check the swimming conditions here.
Go Kayaking in the River
A fun way to enjoy city views is to go kayaking in the Chicago River or in Lake Michigan. You can rent a kayak in the Chicago River here and Ohio Street beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Listen to Free Music Concerts in Millennium Park
A great Chicago activity in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.
The annual Grant Park Music Festival is the only free outdoor classical-music concert series in the US. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors. Grant Park Music Festival runs through August 15, 2026 – you can see the full schedule here.
The free Millennium Park Summer Music Series (Mondays and Thursdays through August 6, 2026) features a wide variety of music from established and emerging artists.
Listen to Concerts Under The Stars
Enjoy a music concert on a beautiful rooftop with city views. Concerts Under The Stars taking place this summer include:
Sinatra Under The Stars at AIRE Rooftop
Piano Men: A Billy Joel & Elton John Tribute at AIRE Rooftop
You can find the full list of Concerts Under The Stars here.
Listen to Free Live Music at the Museum of Contemporary Art Tuesdays on the Terrace
The Museum of Contemporary Art hosts the popular Tuesdays on the Terrace in the summer. Enjoy free music highlighting artists from Chicago’s internationally renowned jazz community at at MCA’s Anne and John Kern Terrace Garden.
When: 5:30-8pm on Tuesdays through August 25, 2026
Jazzin’ at the Shedd
Listen to live jazz music at the Shedd Aquarium in the summer. The popular midweek Jazzin’ at the Shedd series combines Jazz music, the city skyline, fireworks and animals. Relax with a drink on the breezy terrace and take in their unbeatable city view or stroll the aquarium.
When: 5-10pm on Wednesdays through September 2, 2026
Watch Free Movies Outside
You can watch also free movies every Tuesday (through August 18, 2026) near The Bean at Millennium Park on the state-of- the-art, 40-foot LED screen.
There are several more places you can watch free outdoor movies in Chicago during the summer including Navy Pier, Gallagher Way in Wrigleyville and various Chicago public parks.
Watch Movies on a Rooftop
Want to watch classic movies against the backdrop of the Chicago skyline? You can watch movies outdoors Rooftop Cinema Club, a rooftop located in Fulton Market.
Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St). This is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks.
Join Free Outdoor Summer Workouts
Want to join free yoga (and other exercise classes) while also spending time outside?
The Millennium Park Summer Workouts program offers free yoga, pilates, cardio kickboxing and Zumba classes on most Saturday mornings (through September 5, 2026) at Millennium Park.
Ou can also join free pilates classes at Oak Street Beach every Friday morning around sunrise.
Other places offering free fitness classes in the summer include Navy Pier, Gallagher Way in Wrigleyville and The Green at 320.
Enjoy the Views from a Rooftop Restaurant
Chicago has several rooftop bars and restaurants with amazing views of Chicago. Some rooftops with bucket list worthy views include:
LH ON 22 (85 East Wacker Drive)
Cindy’s at the Chicago Athletic Association Hotel (12 S Michigan Ave)
The J. Parker at the Hotel Lincoln (1816 N Clark St)
Shop and Eat at the Argyle Night Market
The Argyle Night Market is an annual event that features food from local Argyle restaurants plus live cultural and musical performances on Thursday evenings each summer (5-9pm through August 27, 2026).
See the Chicago Air & Water Show
The Chicago Air & Water Show takes place on August 15 & 16, 2026 (Rehearsal on Friday, August 14, 2026).
The show can be viewed for free along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point.
While you can see the Air & Water Show for free from the beach, you can also avoid the crowds by joining one of the following cruises or watch parties:
Air & Water Show Preview at Shore Club
Air & Water Show Watch Party at Caffe Oliva on Ohio Street Beach
Air & Water Show Viewing Party at The Lakefront Green at Theater on the Lake
Air & Water Show Saturday Lake Cruise (21+)
Air & Water Show Viewing Party at The Lakefront Green at Theater on the Lake
Air & Water Show Sunday Lake Cruise (21+)
Watch the Water Displays at Buckingham Fountain
Visit Buckingham Fountain before it is turned off for the season in October. There are now chairs where you can sit down and relax.
Watch a Baseball Game
Even if you are not a fan of baseball, a day at the ballpark is a must for locals and tourists alike. You can buy tickets and see the Cubs schedule here and the White Sox here.
Attend a Outdoor Neighborhood Street Festival
Check out one of the many outdoor neighborhood street festivals taking place in the summer every weekend. Neighborhood street festivals are free but there is usually a suggested donation for entry.
Upcoming neighborhood festivals taking place this summer include: Printer’s Row Art Fest (August 15-16, 2026), Taste of Greektown (August 28-30, 2026), Lakeview Taco Fest (August 28-30, 2026) and Bucktown Arts Fest (August 29-30, 2026).
Attend a Music Festival
While Lolla is over, there are still several music festivals taking place in Chicago this summer: Northalsted Market Days (August 7-9, 2026), Chicago Jazz Festival (September 3-6, 2026), ARC Music Festival (September 4-6, 2026), North Coast Music Festival (September 4-6, 2026) and Riot Fest (September 18-20, 2026).
For more summer events check out my post on the best things to do in Chicago this week which is updated weekly.
These things are the top things to do in Chicago this summer that need to be on your bucket list. Find more things to do in Chicago in the summer here.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
Need more bucket list inspiration? You might enjoy our other travel bucket lists:
