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 summer months are by far the most lively months of the year. Months that we fill with an array of euphoric experiences and enjoyable activities. As well as positive vibes it means numerous days of rallying the troops, agreeing on times, buying tickets, and traveling to and fro, and so forth…
The city is more alive than ever in July and August and there is so so much happening sometimes it can feel challenging trying to check off all the things you want to do. We’ve here rounded up the best plans for a summer in Chicago whether you’re a seasoned local or an inquisitive tourist.
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[/trackLink] 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 largest permanent digital art projection in the world, 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.
Now a new set of projections have begun illuminating the Merchandise Mart for the 2023 summer season including a new commission by the Chicago Black Dance Legacy Project.
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.
16. Check out the Morton Arboretum’s towering new sculptures
A new exhibition has opened at the Morton Arboretum featuring a collection of brand-new towering arbor-inspired sculptures. Titled “Of the Earth“, the exhibition features five exclusive new works from Polish-American artist Olga Ziemska and replaces those on display for Human + Nature.
Having unveiled five breathtaking sculptures by renowned multi-disciplinary South African artist Daniel Popper back in May 2021, Human+Nature was already the largest-ever exhibition of Popper’s work before it then added three additional sculptures in June of 2022.
The adored exhibition then officially closed at the end of February paving the way for “Of the Earth” which opened on May 26 similarly showcasing the largest exhibition of artist Olga Ziemska’s work to date.
According to an official Morton Arboretum release, Ziemska’s sculptures have been predominantly created from reclaimed tree branches and other natural materials gathered from various locations throughout the Arboretum’s grounds.
Read more about the Morton Arboretum’s “Of the Earth” exhibition
17. Explore Chicago’s incredible parks and gardens
Chicago is no far friend from nature. With its lush parks, riverside excursions, the Lakefront, and incredible hiking trails, the city is abound with opportunities to get back in touch with Mother Nature. These offer wonderful paradises alive with growth and wildlife during the summer heat.
We’ve rounded up some of the most celestial secret gardens and parks around Chicago so you can take a look and choose one (or more) this summer for a euphoric day out in nature.
Read our full list of the best natural spots in Chicago.
18. Visit Illinois’ largest waterpark
The largest waterpark in Illinois, Raging Waves, opened for the summer at the start of June for its 16th year. The public can once again enjoy 32 water slides, 43 private cabanas, the enormous wave pool, the relaxing lazy river, and much more.
For those thrill-seekers looking for their fill of adrenaline, Raging Waves is now also home to the first Proslide RallyRACER™ in the Midwest and one of three in the world.
The six-lane mat racing water slide, named Aussie Mat Dash, invites up to 5 friends or family members to rocket down slides next to each other and see who is the fastest of the pack.
19. Spend a Sunday at Maxwell Street Market
Maxwell Street Market, Chicago’s longest-running open-air market, first debuted back in 1912 has returned in 2023 for its 111th summer stretch with handmade crafts and undetected treasures.
Open every Sunday at 800 South Des Plaines Street from 9 am to 3 pm through to Sunday, October 29, shoppers can expect a Sunday of spirited live music, and sensational street food as well as an eclectic array of bric-à-brac.
The historic market makes for a wonderfully wholesome summer activity in the sun.
Read more about Maxwell Street Market.
20. Peruse the local farmers markets
A sign of the thriving summer months is also evident in the return of Chicago’s weekly farmer’s markets. The open-air stalls are always bustling with local vendors and filled to the brim with produce, sweet treats, artisan cheesemakers, and candles alike.
Head over to one of the many markets near you for a special day spent with friends. These markets are a real Chicago highlight and keep going all through summer offering fresh ingredients to feed your summer soul.
Read a full breakdown of Chicago’s farmers markets.
21. Kick back with goats and beer
If there’s one way to relax and let your mind unwind this summer it’s with a pasture full of adorable billy kids followed up by a selection of craft beer.
Brews n ‘Baahhs’ invites you to escape to the idyllic setting of GlennArt Farm for an hour hanging out with their playful and adorable goats before doubling down on those warm fuzzy feelings with a flight of craft beers on the rooftop of One Lake Brewing.
Buy tickets for a Brews n ‘Baahhs’ experience.
22. Make the most of Chicago happy hours
Waiting for Friday after a tedious work week can feel light years away, especially if it’s a dreaded Monday. However, we don’t have to wait until the weekend to see friends and pay for overpriced drinks at a crowded bar to get boozy—a budget-friendly outing awaits you after completing the day’s worth of tasks.
Whether your office is in the loop or your Uptown bedroom, head to the nearest neighborhood bar and take advantage of the best happy hours Chicago has for a midweek excursion.
Read more about the best Chicago happy hour deals.
23. Embrace the peak of patio season at Chicago’s largest patio
Chicago doesn’t play around when it comes to patio season. Come rain or shine, if a patio is opened somewhere in the Windy City, guaranteed Chicagoans are out there clinking drinks. One of the best in the city has to be Recess’s gigantic patio bar.
Nestled within 30 shipping containers on a West Loop corner, Recess is home to a cozy amalgamation of bars, food stands, and cabana houses within a 14,500-square-foot space that holds the title of the largest patio in Chicago. The stacked shipping containers give it an awesome reclaimed industrial vibe while the fusion of plant life and vibrant murals make it a brilliant summer hideout.
Read more about Recess Chicago.
24. Explore Chicago’s most amazing murals
Taling of murals, the street art and graffiti scene in Chicago is alive and kicking more than ever before with new pieces popping up all over the city every week. Some of these are so esteemed that they’ve embedded themselves in the very fabric of Chicago and are now as much part of the Windy City’s identity as its iconic sculptures and landmarks.
Today murals do more than just provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for equality, celebrate different heritages, and honor the heroes of society.
With the summer sun shining, there’s never a better time to plan a walk around the city and check off some of its most marvelous murals.
Check out our extensive list of must-see murals around Chicago.
25. Enjoy the 606 and Lakefront trails
Chicago’s stunning 606 trail is another popular spot for walking, running, and biking. Built on an abandoned railroad line, this elevated multi-use trail is Chicago’s take on NYC’s The Highline. Running through Logan Square, Humboldt Park, Wicker Park, and Bucktown, the trail is full of murals, lookout points, and green spaces offering a unique trip overlooking some of Chicago’s busiest North Side neighborhoods.
The Lakefront Trail on the other hand offers an iconic stretch of 18 miles with the city’s sensational skyline on one side and the blue waters of the lake on the other. From the south of Chicago up to the north, you’ll pass harbors, museums, beautiful beaches, and much more.
Cycling the Lakefront Trail is a wonderful summer activity and bikes can be easily rented for full days or, for complete newcomers, the Chicago bike tour, known as Bikes, Bites, and Brews takes guests on a bike tour tasting signature Chicago dishes and sampling legendary Chicago craft beer along the way.
26. Head out to Starved Rock State Park
A little journey outside of Chicago, but still just a one-tank trip under 100 miles away is Starved Rock State Park. Added to the National Register of Historic Places in 1998, Starved Rock is an incredible natural escape from the city offering over 13 miles of hiking trails, numerous cascading waterfalls, and 18 different canyons.
At any time of the year, the ecological cosmos offers a captivating paradise steeped in both history and beauty. Outdoor enthusiasts, hikers, and nature lovers flock here year-round to reap the rewards of a natural escape so close to the Windy City but it is in summer when it becomes an easy and enjoyable day out for family and friends.
Read about our seven natural wonders of Illinois.
27. Take a break by visiting small towns near Chicago
There are so many reasons to be titillated with Chicago—stunning architecture, a vivacious music scene, and savory restaurants at every corner—however, every so often, we all need an escape.
While there are many options for beautiful small towns in the vicinity of Chicago, distinctive historic ones stand out. Whether you want to meander down a secluded beach at sunset or peek into an antique shop for a treasured book, these small towns near Chicago will make you feel as if you have fallen straight into the scene of a Nicolas Sparks film.
Escape the city with local wineries, cobblestone streets, and beach sunsets at these enchanting small towns just a few hours away from Chicago.
Read about some of the most beautiful small towns near Chicago.
28. See out summer with the Chicagohenge autumn equinox
Ok ok we know, this is the end of summer but it is also one of the most stunning spectacles of the year and it’s a brilliant way to mark the end of summer and the beginning of fall.
Due to Chicago being built on a grid system and streets lining up near perfectly on compass north to south and east to west, the sun lines up with Chicago’s east-west facing streets and beams down the heart of the city during the spring and fall equinoxes.
The magic of nature and Chicago’s glorious architecture collaborate harmoniously to put on a breathtaking spectacle that people from all over come to witness.
[Featured image from Shutterstock]