As our thriving metropolis moves into summer temperatures, riverside bars, lakefront beaches, and our plethora of phenomenal parks all begin to blossom with jubilance.
The city is more alive than ever in July and August, and there is so much happening. Sometimes, it can feel challenging trying to check off all the things you want to do. Whether you’re a seasoned local or an inquisitive tourist, we’ve rounded up the best things to do in Chicago this summer.
1. Hit the beach
We may be miles away from the ocean, but that doesn’t mean we can’t enjoy some top-notch beaches. For obvious reasons, places like North Avenue Beach, Oak Street Beach, and Ohio Street Beach have become some of the most popular places to be during the summer months as Chicago heats up.
Whether playing volleyball, renting paddleboards, or having a lazy day on the sand, you just can’t beat a day kicking back and looking out over Lake Michigan.
There are also plenty of great beachy hangouts like Shore Club Chicago, The Waterfront, Castaways, Cafe Olivia, and many more.
2. Hang out on the Riverwalk
Of course, another of Chicago’s most frequented spots in summer is the beloved Riverwalk. From bohemian hideouts to ritzy restaurants that’ll have you feeling like you’re on the Italian Riviera, the Riverwalk is full of fantastic places for food and drinks.
Start near DuSable Harbor and make your way west, from there stop off at wherever takes your fancy. Soak in the views of Chicago and enjoy some prime people-watching spots.
Read the full list of our favorite waterfront dining options.
3. Watch a firework display on Navy Pier
Of all the things that forecast summer’s impending arrival, the start of Navy Pier’s summer program of events is one of the most symbolic.
On Saturday, 27 May Navy Pier launched its first summer firework show kicking off its summer programming and weekly firework displays every Saturday at 10 pm and every Wednesday at 9 pm through Labor Day weekend.
Onlookers can find a spot anywhere on the pier to take in the dazzling display completely free of charge. According to the Navy Pier website, there will be accompanying soundtracks featuring dramatic and popular music.
Read more about Navy Pier firework displays.
4. Enjoy a summer cruise
If you’re looking to push the boat out this summer, regular booze cruises on Lake Michigan offer an unforgettable night on the water while firework booze cruises provide a particularly memorable experience of the Navy Pier firework displays.
Enjoy live DJ sets spinning the best feel-good tunes whilst taking in breathtaking views of the sun setting over Chicago’s architecture before being treated to unobstructed views of Navy Pier’s week fireworks shows!
Buy tickets to a Chicago summer cruise.
5. Enjoy one of State Street’s block parties
In 2021, with the pandemic still lingering Chicago Loop Alliance announced an exciting new project to “bring people safely back to the Loop”.
The project was an ambitious weekly summer street festival that saw closed off State Street from Lake to Madison on Sundays throughout the summer. Called ‘Sundays on State’, the event aimed to revive the Loop’s economy with a wide range of attractions and activities that would give pedestrians “a chance to experience arts and culture, active recreation, retail, restaurants, and bars against the backdrop of State Street’s iconic architecture.”
Dubbed as a trial in 2021 with hints that it could become a regular summer occurrence depending on how it went, Sundays on State returned with an expanded footprint last year due to its hugely successful inaugural year.
This year the summer block party is returning for two select dates in July and August.
Read more about Sundays on State.
6. Watch the Ducky Derby
Every summer, over 60,000 yellow ducks splash away in the Chicago River in a lip-biting race to the finish line to raise money for Special Olympics.
Thousands of Chicagoans flock to the downtown area to watch the spectacle and many adopt ducks for $5 each or go big with a Quack Pack (six ducks) for $25! The event raises upwards of $300,000 for over 20,000 athletes and more than 10,000 young athletes.
This year, the 18th Annual Chicago Ducky Derby will take place on Thursday, August 10 from the Columbus Drive Bridge on the Chicago River.
Read more about the Chicago Ducky Derby.
7. Gaze at the skies for the Chicago Air and Water Show
One of the most popular of August events can be found in the skies above Chicago this summer. The Chicago Air and Water Show will return in August to wow spectators lined up along North Avenue Beach and the Lakefront from Fullerton to Oak Street once again.
Presented by the City of Chicago it is the largest free show of its kind in the entire country and features a variety of military and civilian performances.
On Saturday, August 19, and Sunday, August 20 the Navy Blue Angels, the Golden Knights Army Parachute Team, and multiple other performers will take to the skies from 10 am until 2 pm.
Free on both days, it will once again be a full-scale Chicago Air and Water Show after it was canceled in 2020 and resorted to a scaled-back version in 2021.
Read more about the Chicago Air & Water Show.
8. Get involved with Chicago’s annual Bike the Drive event
Every year thousands of cyclists, both rookies and seasoned veterans, flood the 30-mile stretch of car-free Lake Shore Drive (now known as Jean Baptiste Point DuSable Lake Shore Drive). With sweeping views of the lake and skyline, riders can cycle as little or as much of the 30-mile course as they’d like and then enjoy a post-ride festival in Grant Park.
This year the event will be taking place from 6:30 am until 10:30 am on Sunday, September 3, 2023. The festival meanwhile will take place from 8 am until 12:30 pm. There are bike rentals available for those who wish to participate but don’t own a bike.
Read more about Chicago’s Bike the Drive event.
9. Catch the Art on TheMART summer projections
Holding the title of the world’s largest permanent digital art projection, Art on theMART attracts thousands to the Riverwalk and Wacker Drive in downtown Chicago every week from spring through fall by transforming the 2.5-acre river façade of the Merchandise Mart.
The 30-minute shows currently run twice nightly at 9 pm and 9:30 pm. The best places to view the projections are from the jetty section of the Chicago Riverwalk between Wells and Franklin Streets.
Read more about Chicago’s Art on TheMART projections.
10. Kayak down the Chicago River
There are few better ways to see the city than by kayaking down the Chicago River in summer. Flanked on either side by Chicago’s famous highrise architecture, you can venture through the city’s heart via skyscraper canyons and under historic bridges.
An evening kayak makes for a truly memorable night navigating the waters while the sun sets and the hustle and bustle of the riverwalk activity takes off around you.
Single kayaks, tandem kayaks, and kayaking tours are all available, allowing you to navigate Chicago’s winding river at whichever pace you desire. Learn about the sights with a tour guide, or explore the river independently and see where it takes you.
You can also paddle past the aforementioned Art on the MART projections for a truly memorable evening.
Read more about kayaking experiences in Chicago.
11. Take it to the rooftops
From the waters of Chicago to the rooftops up among the Windy City’s sublime skyline. Among its soaring cityscape, numerous rooftops can be found offering exhilarating experiences drinking and dining among the skyscrapers of Chicago. You will struggle to find a more memorable Chicago evening than one spent sipping cocktails under the stars on a summer’s night.
Of the many choices, there is always something happening at River North’s vibrant and verdant Joy District rooftop whilst an iconic experience can be had at Cindy’s Rooftop in the Loop where you’ll find sweeping panoramic views of Millennium Park and award-winning cocktails from a lavish setup.
Few rooftops can better the stunning vistas of the Chicago River and Michigan Avenue found at London House Chicago however.
Read the full list of our favorite Chicago rooftops.
12. Cool off at a rooftop pool
A winning formula can be found by combining rooftops and cooling off in the water. Although Lake Michigan is practically in everyone’s backyard, we sometimes need an escape from the unpredictable boundless waves for something more serene, and that’s when we can again look to higher ground.
From luxurious hotels to member only-clubs, Chicago is beaming with rooftop pools, and finding the right one can be tricky, so head to our complete guide to rooftop pools to find our favorites that you can lounge at this summer.
Read our top recommendations for rooftop pools.
13. Watch an outdoor movie
With the weather allowing outdoor fun to thrive, another fantastic summer plan comes in the form of catching an outdoor movie showing.
From a lakefront screening to a projector in the middle of a baseball field, you’ll find an open-air screening at almost any Chicago park. So, pack a picnic of your favorite snacks and drinks, keep a cozy blanket on hand, and round up your friends to indulge in the perfect movie night.
Check out our full summer guide to free movie screenings in Chicago.
14. Kick back at MCA’s free ‘Tuesdays on the Terrace’ summer concerts
One of the most anticipated free summer experiences in Chicago comes in the form of the Museum of Contemporary Art’s free Tuesdays on the Terrace — a free musical event series for Illinois residents that runs from mid-June to late August each year.
Offering Chicagoans the chance to turn the average underwhelming Tuesday into a jubilant evening at the MCA’s Anne and John Kern Terrace Garden, Tuesdays on the Terrace.
Running from 5:30 pm until 8 pm, the free shows will take place every Tuesday through August 29, 2023, highlighting artists from Chicago’s internationally renowned musical community all summer long.
Though traditionally hosting jazz performances, the Museum of Contemporary Art has announced that this year, for the first time it is branching out beyond its jazz focus to include more diverse genres and styles that have unique Chicago roots.
Read more about Tuesdays on the Terrace.
15. Be captivated by an outdoor Candlelight Concert
Talking of outdoor concerts, Chicago’s sublime Candlelight Concert series offers breathtaking spectacles throughout the year but in summer extra special concerts take place in extraordinary outdoor and indoor venues all over the city.
Flickering candles and melodic sounds combine phenomenally to create magnetic atmospheres in some of Chicago’s most unique spaces.
See the full list of candlelight concerts taking place in Chicago.