Chicago's Ultimate 2023 Summer Bucket List (2024)

It's finally here: Summertime in Chicago. And that means the Playpen is open for days on the water, free outdoor concerts and movies are back, and our favorite patios, beaches, day trips, and festivals are calling our names!

To make things easy, we rounded up all the events and activities you need to add to your 2023 summer bucket list in Chicago. Grab some sunscreen, put on your shades, and get ready to make the most of Summertime Chi. 😎

This year's summer bucket list is sponsored by Long Drink, a top-selling category of alcohol in Finland that's now available in America. Long Drink is helping Chicago have the happiest summer ever by giving away $1000 in summer bucket list experiences from our site! Enter to win by sharing this post to your Instagram story and tagging @longdrink and @chicagobucketlist!

The Best Things to Do in Chicago This Summer

Hit the Shore for a Beach Day

Visitors may not always know about the beach options in Chicago, but thanks to Lake Michigan, there are 26 official stretches of sand near the city! North Avenue Beach is Chicago’s most popular, and during the summer, you’ll find the spot packed with people enjoying volleyball games, sandcastles, and jumping in and out of the lake to cool off. If you’re on the Southside, try Foster Ave or 63rd Street!

Where: Various locations.
More information.

Shop Local at Chicago Farmers Markets

Summertime makes eating berries and fruits while strolling in the sun even better. Fortunately, Chicago has so many neighborhood markets that finding one to fit your schedule is easy. The Green City Market, for example, hits the streets in Lincoln Park on Wednesdays and Saturdays. The always-happening Logan Square Farmers Market between Milwaukee and Whipple Street starts in June!

Where: Various locations.
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Visit the Malibu Barbie Cafe

Take a mini trip to California by visiting the Malibu Barbie Cafe! This colorful wonderland offers fun food and drinks with unmatched vibes, so make sure you stop by while this unique pop-up is in town.

Where: 324 South Racine Avenue, Chicago, IL
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See the Cubs Play from Wrigley Rooftops

It’s not summer without a trip to see the Cubs play. This year, get a unique view of the game from Wrigley Rooftops! Perfect for group outings or parties, you can choose from 11 unique rooftops along Waveland and Sheffield avenues and take in unobstructed views of the game without the crowds. Plus, it's all-inclusive, so all you have to do is show up—the drinks, food, and fun are taken care of!

Where: Various locations.
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Tailgate Lake Michigan on a Party Boat Cruise

A great summer requires a great lake, and Bucket Listers is excited to partner with Tailgate the Lake Charters to offer you exclusive pricing to the party boat cruise of our dreams! For three hours, you and 13 of your crew can set sail, play beer pong and flip cup, and dance the day away in and out of the water. Reservations start May 2023 and go all summer long.

Where: 400 East Monroe Street, Chicago, IL
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See Free Movies & Concerts at Millennium Park

Whether you’re more into film or music, Millennium Park has a summer option for you. Bring your own food, drinks, blankets, and chairs, and settle in for some incredible free entertainment. Films are every Tuesday, while music happens on Monday or Thursday. Make sure to check the schedule for the most up-to-date information!

Where: 201 E Randolph St., Chicago, IL
More information on Film Series and Music Series.

Race in the BTN Big10K

Rep your Big Ten school in this iconic summer event. Wear your school-specific shirt and join thousands of Big Ten alums on July 15. Run/walk a 5K or 10K along the beautiful Chicago lakefront. After the race, join your fellow alums and the Big Ten mascots for the biggest Tailgate party in the Midwest! All runners get a Big Ten medal, sunglasses, and free professional photos from the event.Register here.

Where: Soldier Field, Chicago, IL
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Try Some Cheesecake at the Golden Girls Kitchen

Get ready to be completely immersed in the world of Golden Girls! This iconic pop-up has made its way to Chicago and includes nods to many of the Golden Girls' favorite Miami spots. True fans will appreciate the details and decor, and new fans will fall in love. Get ready to take plenty of photos—and don't forget the cheesecake!

Where: 1367 North Milwaukee Avenue, Chicago, IL
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Grab an Iced Coffee and Shop Along Armitage Ave

Located in the vibrant Lincoln Park neighborhood, Armitage Ave has become a hub of trendy boutiques and shops you can spend the day browsing! For a luxe weekend morning this summer, grab a coffee at La Colombe (we love their semi-sweet oat milk lattes), and snag a small-batch, colorful vegan donut at Beacon Donuts to fuel up.

Then, explore the numerous shops along the lengthy street, including a definite visit toOutdoor Voices, some creative inspiration at needlework shop Third Coast Stitches, and another stop at the quirky home decor shop Art Effects.

Where: 955 W Randolph St to start at La Colombe, Chicago, IL
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Attend a Summer Show

There are so many great concerts and shows coming to Chicago this season. Check out Hot Summer Nights featuring Shaggy and TLC in June, or relive your emo days at Sad Summer Fest, headlined by Taking Back Sunday in July. And, of course, Grant Park will once again host Lollapalooza, showcasing over 170 bands across nine stages in August.

Where: Various locations.
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Sample Brews at Chicago Craft Beer Fest

Chicago Craft Beer Festival is back for its tenth year at Jonquil Park. Enjoy refreshing cold brews and sample up to 12 beers from Illinois breweries. Or, spring for the VIP package, which includes 12 standard sampling plus 5 additional specialty craft beer tastings, a custom-tasting glass and keepsake, a private seating area and restrooms, and an exclusive entrance for easy access to the event.

Where:Jonquil Park: 1001 W. Wrightwood Ave, Chicago, IL
More information.

Get Moving at a Fitness Festival

Looking to work on your fitness game this summer? This festival at North Avenue Beach on June 24 will have 40 fitness instructors, 24 classes, and 8 studios ranging in everything from spinning and strength training to dance and boxing. If you're looking for something more chill, try out a sound bath or yoga session. There will also be six stages, three bars, and two live DJs—come for the fitness classes and stay for the music, drinks, and summer beach vibes.

Where: North Avenue Beach, Chicago, IL
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Experience Glow in the Park

For a nighttime summer adventure, you need to check out Glow In The Park! On select Friday nights, you can try this unique climbing and zipline experience at The Forge under the stars with special lights, music, glow sticks, and more. Enjoy ropes course obstacles, rock climbing, rappelling, and a 1000-foot zipline over The Forge Quarry.

Where: The Forge: Lemont Quarries: 1001 Main St, Lemont, IL
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Attend Taste of Randolph

Taste of Randolph is back for another year, bringing together the biggest and brightest names in Chicago dining. Spend a summer afternoon sampling food from over 16 restaurants with delicious menus and unique flavors. You'll also enjoy live music from up-and-coming bands and musicians, as well as the biggest names in Chicago house music, performing on two stages and a DJ stage!

Where: 900 W Randolph St., Chicago, IL
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Summer Nights at the Ballpark

A leisurely afternoon at the ballpark is a classic summer staple for a reason. Stop by Guaranteed Rate Field to catch the White Sox in action. With a cold beer and hot dog in hand, there’s no better way to spend a summer night.

Where: 333 W 35th St, Chicago, IL
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Kayak on the Riverfront

From Happy Hour to sunset, there’s a kayak tour for everybody! Spend an afternoon on the lakefront in Monroe Harbor, where you’ll experience calmer paddling conditions that are perfect for beginners and families.

For a little more adventure, rent single and tandem kayaks along the Chicago River location! This is for the slightly more experienced paddlers, but it offers an up close and personal view of the city's coolest buildings and is a major hit for tourists and residents alike to view the city.

Where:
Lakefront Location: 110 N. Lakeshore Dr, Chicago, IL
Riverwalk Location: 435 E. Chicago Riverwalk,Chicago, IL
More information.

Celebrate Chicago Pride

Pride Fest is back on June 17 and 18 this year, and it’s bigger and better than ever, with three stages, incredible food and drinks, arts and craft vendors, drag shows, and a pet parade. Then, on June 25, watch the annual Chicago Pride Parade!

Where: 800 W Waveland Ave, Chicago, IL
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Go To a Y2K Beach Party

Pull on your low-rise jeans, grab your flip phone, and party like it’s 2003 at North Avenue Beach on June 24. This Y2K Beach Party celebrates the era that brought us Boy Bands and defined the millennium with groundbreaking music, tech, and fashion. Enjoy a huge beachfront beer garden, live DJs, immersive photo ops, a foam party, a silent disco, beach volleyball, and more!

Where: North Avenue Beach, Chicago, IL
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Watch a Drive-In Movie

Drive-in movies are back this summer! With the city skyline as your backdrop, you can cozy up in your car and enjoy classic films or new releases on the big screen while munching on your favorite snacks. Come early, bring lawn chairs to set up outside of your car, order tacos and beers from the bar and grill and enjoy the movie under the stars.

Where: 2343 S. Throop Street, Chicago, IL
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Check Out Summer Events in Rosemont

You may not know it, but Rosemont, located just 30 minutes from downtown Chicago, is full of amazing restaurants and unique entertainment—and it has a packed schedule of summer events. From a free Fitness in the Park series beginning in June to a Classic Car Super Show in July, there's something for everyone.

Kicking off summer festivities on Memorial Day Weekend is the return of the free summer concert series, "Rockin’ in the Park." Every Thursday and select Friday and holiday evenings from June 1 through August 31, you can swing by and catch live music alongside food and beverage tents. Bonus: Thursday night concerts will culminate with a musical fireworks display!

Where: Rosemont, IL
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Take a Day Trip to Starved Rock

Even the most loyal city dwellers occasionally need a change of pace. Luckily, Chicago is surrounded by nature, art, breweries, and more—perfect for road-tripping this season.

In less than two hours, you can breathe the fresh air and take in the beautiful views of Starved Rock State Park. They even offer river cruises if you're feeling extra adventurous. For more ideas, check out our roundup ofthe best day trips from Chicago.

Where: One Lodge Lane, Oglesby, IL
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See Live Comedy on a Rooftop

Every Sunday this summer, you can enjoy some laughs on The Comedy Bar’s rooftop patio. Featuring a mix of local acts along with national headliners, breathtaking views of the Magnificent Mile, and a full dinner menu from Chicago’s famous Gino’s East pizza, this is the ultimate comedy experience. Tickets include seating and a welcome drink!

Where: Comedy Bar: 162 E Superior St, Chicago IL
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Wake Surf on the Lake

If you love to be on the wateror simply want to explore more of Downtown Chicago, there’s a new experience with your name on it. Wakesurfing is a towable sport that can provide a smooth surfing experience right on Chicago’s sparkling lakefront!

Boat drivers, surf instructors, life jackets, towels, wetsuits, and boards—plus water and other refreshments—are all provided so all you have to do is show up and practice your 360s.

Where: Diversey Harbor: 2601 N Cannon Dr, Chicago, IL
More information.

Dine al Fresco at Chicago's Best Patios

Dining al fresco is in Chicagoans' DNA—and warmer weather certainly helps! Whether it's the 80-seat, globally-inspired patio at Beatnik on the River, enjoying co*cktails and Mexican eats under the wood beams of Pilsen Yards, or sharing oysters at hipster vintage saloon The Frontier, you can’t go wrong.

Where: Various locations.
More information.

Explore the Gold Coast Art Fair

Calling all art lovers! On July 17 and 18, the Gold Coast Art Fair returns to Grant Park with amazing art, music, and activities. Flex your own skills at the Paint and Sip activation, which includes a one-hour lesson and a premium drink (exclusive to Bucket Listers ticket holders!).

Where: Grant Park: Butler Field: S Lake Dr & E Monroe St, Chicago, IL
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See Chicago's Shores with a Boat Trip Around Lake Michigan

This summer sailing adventure offers spectacular views and an unforgettable day on the water. Choose from a variety of sails, including an afternoon tour featuring true stories of piracy, an evening tour featuring architecture and Chicago's skyline, or even a Pirates Pub Sail where you'll listen and sing to the traditional songs of the pirates!

Where:Navy Pier: Tall Ship Windy 600 E Grand Ave
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Listen to Jazz at Shedd Aquarium

The popular midweek Jazzin’ at the Shedd series returns this June with an exciting lineup of Chicago’s top jazz ensembles. Between listening, visitors can relax with a drink on the airy terrace with gorgeous city views or stroll through the aquarium and see the unbelievable animals that live inside.

Where: 1200 S. DuSable Lake Shore Drive, Chicago, IL
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Cool Off with a Sweet Treat

If you need an excuse to grab yourself a frozen treat, consider this your sign. Stop by Rainbow Cone, and try the city's most colorful cold dessert. Annette's is a longstanding ice cream shop in Lincoln Park and has some of the best cold sweet treats around, or try Ava's Italian Ice for a flavorful sweet treat that has no artificial colors, flavors, or sweeteners and boasts organic fruit in every recipe.

Where: Various locations.

Try Yoga After Dark

Sunset yoga and a glass of wine? What more could you want? This summer, you can enjoy twilight yoga at either Happy Camper Pizza or Paradise Park, and each event ends with a little vino.

Where:
Happy Camper Pizza – Wrigleyville: 3458 N Clark St, Chicago, IL
Paradise Park: 1913 W North Ave, Chicago, IL
More information.

Charter a Private Yacht

Grab your hats and sunscreen, and get out on the water on a private boat! Perfect for summer celebrations and making memories with friends, every boat includes multiple entertainment zones, a Bluetooth sound system, and a kitchenette. They're also BYOB, so you can get a little wild if you want to while seeing the city from a whole new point of view.

Where: 3155 South Lake Shore Drive, Chicago, IL
More information.

Attend a Hard Seltzer Festival

All of the nation’s top seltzer brands are gathering for Seltzerland, a new kind of adult beverage event. On June 10, you can try dozens of refreshing canned hard seltzers, plus enjoy guacamole and chips, a live DJ, Instagrammable photo-ops, tons of games and activities, and plenty of swag to take home.

Where: 1340 W Washington Blvd, Chicago, IL
More information.

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