30 Exciting Bucket List Ideas For The Perfect Chicago Summer

Nowhere appreciates summer like Chicago.

As our thriving metropolis moves into summer temperatures, riverside bars, lakefront beaches, and our plethora of 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. Places like North Avenue beach, Oak Street Beach, and Ohio Street Beach become some of the most popular places to be during the summer months as Chicago heats up, for obvious reasons.

Whether you’re playing volleyball, rented 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 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.

3. Enjoy a Concert Under The Stars

Concerts Under The Stars will set you back in time with unique vintage sounds in beautiful star-lit venues. Experience the works of Sinatra, Ella Fitzgerald, Amy Winehouse, moving movie ballads, and more presented by Chicago’s finest while sipping a martini in a jazz-age vibe.

Both Sinatra Under the Stars concerts and From Ella to Amy: A Tribute to Female Jazz Legends concerts are taking place on the Aire Rooftop at the Hyatt Centric The Loop Hotel and the stunning Guild Row Rock Garden in both July and August.

There will also be an extra special Tribute to Frankie Valli & The Four Seasons on the Aire Rooftop on the 2nd and 30th of August.

4. Catch the Art on the MART 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.

34 digital projectors display moving art created by local artists, and international artists as well as work from schools and renowned exhibitions.

From Thursday, June 30, at 9 pm, the mart will be showing Billiken by Shkunna Stewart and Wills Glasspiegel, explore by Jonas Denzel, and Nick Cave’s Ba Boom Boom Pa Pop Pop.

5. 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 Art on the MART projections for a truly memorable evening.

6. Watch a firework display on Navy Pier

Another great waterside location is of course our beloved 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, 28 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.

7. Enjoy a yacht party

If you’re looking to push the boat out this summer, regular weekend booze cruises offer an unforgettable night on the water.

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!

8. Take it to the rooftops

From the waters of Chicago to the rooftops 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. The photographer’s paradise has been revamped for a botanical rooftop “Luminescence” experience that will last all through summer.

9. 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. Every Tuesday from July 12 through August 30, movies are shown on Millennium Park’s state-of-the-art, 40-foot LED screen. Guests may take a seat at the Jay Pritzker Pavilion or lounge on the Great Lawn and catch movies like Encanto and Harry Potter and the Sorcerer’s Stone.

There are also free movies on Mondays from July 18 through August 29 at Navy Pier with a focus on families, and free movie showing at Gallagher Way in Wrigleyville on select Wednesdays through the end of September.

10. Be captivated by an outdoor Candlelight Concert

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.

11. Check out the Morton Arboretum’s towering sculptures

This year Chicago’s beloved Morton Arboretum will celebrate its 100-year anniversary. To celebrate such an occasion, the 1,700-acre tree museum and research center is kicking off a yearlong centennial celebration building up to its 100th birthday. Already an incredible place to visit any season of any year, the Arboretum is currently home to 8 enormous arbor-inspired sculptures by renowned multi-disciplinary South African artist Daniel Popper.

After opening in May of 2021, the Morton Arboretum’s arbor-inspired exhibition ‘Human + Nature‘ has been a huge success. The arboretum has now added three brand-new sculptures to the mix which will now be on show through May 2023.

As well as being the largest exhibition of Popper’s work to date, the sculptures were crafted especially for Arboretum visitors. They feature a merge of technology and nature highlighting the deep roots between humans and trees.

12. Explore parks

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.

13. Visit Illinois’ largest waterpark

The largest waterpark in Illinois, Raging Waves, opened for the summer on June 4 and is celebrating its 15-year anniversary. 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 Illinois 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.

14. Jump around on the world’s biggest bounce house

The world’s biggest bounce house (The Big Bounce America)is currently bouncing its way across North America on a multi-city tour and will spring up just a hop, skip, and a jump away from downtown Chicago in suburban Rolling Meadows’ Busse Park.

Covering an area of just over 13,000 square feet and towering at 32 feet from the ground, the behemoth Guinness World Records-certified World’s Biggest Bounce House will offer children of all ages a weekend to remember from Friday, July 22nd, to Sunday, July 24th.

With candy-colored turrets, basketball hoops, ball pits, climbing towers, giant slides, and a DJ the crazy inflatable landscape promises a spectacular summer experience for all the family.

15. Check out State Street’s weekly interactive block parties

Last year, with the pandemic still lingering Chicago Loop Alliance announced an exciting 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 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 last year, it is now coming back with an extended footprint, 250 artists, businesses, workshops, and more after a hugely successful inaugural year.

16. 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.

17. Visit Chicago’s new Museum of Ice Cream

When you think of the summer months you usually imagine sun, beaches, patios, and ice cream. The latter is synonymous with summer all around the world and luckily Chicagoans are about to be treated to a museum dedicated entirely to ice cream.

The Museum of Ice Cream, a fabulous wonderland for all things colorful, will open its doors in the Windy City on Saturday, July 16th. Described on the Museum of Ice Cream website as “a Willy Wonka factory come to life that you won’t want to leave”, the exciting new museum will feature 14 magical and interactive installations reimagined just for Chicago.

The new Michigan Avenue location, the fourth Museum of Ice Cream on the planet, will span over 13,500 square feet of The Shops of Tribune Tower where the Chicago Tribune formerly resided. Guests will be invited on 60 to 90-minute tours through the many ice cream-themed features with breaks to sample various sweet treats between enjoying the installations.

18. 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 ducks will race on August 4 from the Columbus Drive Bridge on the Chicago River.

19. Gaze at the skies for the Chicago Air and Water Show

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 the 20th and 21st of 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 be the first full-scale Chicago Air and Water Show since 2019 following a full cancellation in 2020 and a scaled-back version featuring a solo demonstration by the Navy Blue Angels in 2021.

20. Hit up the Salt Shed this summer

Early last year the Chicago City Council approved plans to redevelop the old Morton Salt Factory for nonindustrial use. The Elston Avenue property is known for the enormous “Umbrella Girl” sign that can be seen from the Kennedy Expressway. After purchasing the property from Morton Salt for $15 million in 2017, Chicago developers, Blue Star Properties and R2 were given the thumbs up to redevelop the property for nonindustrial use and turn it into an exciting new riverfront music venue.

Roll on over a year and an estimated $50 million+ later and the new venue, dubbed ‘the Salt Shed’, will kick off an exciting lineup of concerts on Wednesday, August 3rd beginning with an outdoor show from indie-folk band Fleet Foxes. Other summer highlights include performances from Jorja Smith, Angel Olsen, Iron & Wine, and Sharon Van Etten.

21. Attend a Tuesday on the Terrace at MCA

Every Tuesday through summer, the Museum of Contemporary Art hosts Tuesdays on the Terrace — a free musical event series for Illinois residents. It offers Chicagoans a chance to turn the average underwhelming Tuesday into a jubilant evening at the MCA’s Anne and John Kern Terrace Garden experiencing free music that highlights artists from Chicago’s internationally renowned jazz community.

Two sets of live music take place every Tuesday evening from 5:30 pm and run until 8 pm through August 31.

22. 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 and often well into the fall season.

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.

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. Chicago’s art scene is unparalleled and with the many talented local artists frequently at work, it is equally as exciting for both tourists and locals alike. With the summer sun shining, there’s never a better time to plan a walk around the city and check off some of the most marvelous murals.

Many of these wonderful murals reside in West Town in the mile-long street art corridor in Chicago’s Fulton Market meatpacking district known as the B_Line. With the West Town Street Art Walking Tour run by Tours By Native you can enjoy an immersive tour that will engage the senses like never before! Alternatively check out our extensive list of must-see murals around Chicago here.

25. 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.

26. 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 andbikes 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.

27. Admire the magic of Grant Park’s Buckingham Fountain

Inspired by one of the fountains at the Palace of Versailles in France but more than double its size, Chicago’s beloved Buckingham Fountain in the center of Grant Park is one of the world’s largest fountains. Operational from early May through mid-October the fountain is synonymous with Chicago’s more pleasant months.

Running from 8 am to 11 pm daily it produces a major water display for 20 minutes every hour on the hour shooting water to a height of 150 feet up into the air. Every evening at 10:35 pm an extra spectacular show concludes the day with an accompanying light and music display.

Location: Columbus Drive (301 East) and Congress Parkway (500 South) in Grant Park.

28. Marvel at a 360° exhibition featuring the iconic art collection of the Louvre™

The Musée du Louvre™ in Paris is undeniably one of the most iconic and recognizable art museums worldwide, drawing over 7 million visitors a year to its famous rhombus-shaped glass museum.

This summer Louvre™ Fantastique: The Exhibition will come to the Chicago area offering art lovers the chance to marvel at some of the world’s most astounding artworks. Opening on July 15th Louvre™ Fantastique: The Exhibition offers a 360° experience, showcasing over 70 reimagined masterpieces that are famously on display at the Louvre™.

More information and tickets can be found here.

29. 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 – 10:30 am on Sunday, September 4, 2022. 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.

More information can be found at bikethedrive.org.

30. 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]