Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right Illinois icon-chevron-right Chicago icon-chevron-right Find your fun in Chicago this summer

Find your fun in Chicago this summer

Raise your fun factor this summer with our guide to the best events and activities in town—and how to kick the good times up a notch
Time Out in association with Crocs |

Chicago summers are packed with fun things to do—from biking the 606 to picnics in the city's many parks to hopping on a water taxi and zooming down to Chinatown. This season, though, we want to get out there and explore even more, so Time Out is teaming up with Crocs to really amp up your summer. First, we’re helping you find your fun with great activities right near you; then, we’re telling you how to take that fun to the next level. Try these great fun starters and use the hashtag #FindYourFun to show off your best summer yet.

See The SpongeBob Musical

Take the kids to see SpongeBob Squarepants and friends come to life on stage at the Oriental Theatre (24 W Randolph St), with original songs by more than a dozen rock and pop stars like Cyndi Lauper, John Legend, Sara Bareilles and Panic! At the Disco.

Make it more fun: Kids whose rock & roll imaginations are stirred by the music can toss on a pair of Kids' CrocsLight Fire Dragon Clogs and further their education at School of Rock Chicago and get a head start on writing a musical of their own. Shop now.

North Avenue Beach was the perfect place to watch aerial acrobatics at the Chicago Air and Water Show on August 15, 2015.
Photograph: Anthony Soave

Go to the Air & Water Show

See planes soar through the sky and boats speeding across Lake Michigan at the Air & Water Show (North Avenue Beach, 1600 N Lake Shore Drive), an annual display of death-defying stunts that draws thousands of curious onlookers to North Avenue beach.

Make it more fun: Show off your Isabella Sandals while relaxing and playing oversized Jenga on the city’s largest outdoor rooftop terrace during the Streeterville Social rooftop at the Loews Hotel (455 N Park Drive), all while stunt planes loop by on the horizon. Shop now

Lagunitas showed off its new Douglas Park brewing facility and taproom.​
Photograph: Martha Williams

Visit the Lagunitas Taproom

Take a trip to the gigantic Lagunitas Brewery (1843 S Washtenaw Ave), near Douglas Park on Chicago’s Southwest Side, where you can try some hop-heavy beers in an elevated taproom that overlooks the production floor.

Make it more fun: Take a tour of the brewery. Slip on some Yukon Mesa Clogs and take a guided walk along the brewery’s extensive catwalk system, where you’ll learn more about how Lagunitas brewers make all of those delicious beers. Shop now

Taste of Chicago
Photograph: Martha Williams

Head to Taste of Chicago

Grab lunch at Taste of Chicago in Grant Park (337 E Randolph St), with tasty, cheap bites from local vendors all over the city, from food trucks to pop-ups.

Make it more fun:  Stay late for the concert in a pair of Isabella Sandals or, better yet, take the day off and stay late for drinks and free concerts while you chow down on some of the city’s best. Shop now


Take a distillery tour

There are plenty of distilleries in Chicago, so just pick one—Few, Rhine Hall and KOVAL (5121 N Ravenswood Ave) all have tours, and learn a bit about some local spirits.

Make it more fun:  Slip on a pair of Leigh Graphic Wedges and take a cocktail class at KOVAL. For $30, you can take classes on bartending basics or a seasonal class about brushing up on your cocktail mixing skills, so you’ll be in style both in front of and behind the bar. Shop now

Photograph: Andrew Nawrocki

Spend a day at Chicago Gourmet

With tents upon tents of the city’s best restaurants offering tastings of their menus and wine and beer samplings, it’s easy to spend the day eating your way through the festival and lounging in the sun in Millennium Park (201 E Randolph St).

Make it more fun:  Hit the VIP Lounge Area in a pair of Leigh Graphic Wedges. The Harris Theatre Rooftop will host a wine tasting and gourmet spirits for a reprieve from the sun with savory sips. Shop now

Photograph: Mark Wright

Tour the Beverly Arts Center

Appreciate work by local, regional and national artists when you peruse this gallery (2407 W 111th St) in the historic Beverly/Morgan Park neighborhood.

Make it more fun:  Take the little ones in their bright pink Kids’ Karins Clogs and head to Original Rainbow Cone (9233 S Western Ave) for even more color and sweetness. Shop now

Big Star is one of the best spots for outdoor dining in Chicago.
Photo: Martha Williams

Drink a margarita on the Big Star patio

Order a pitcher on the sunny Big Star (1531 N Damen) patio with a group of friends and order a few tacos as the sun sets.

Make it more fun:  Slip on a pair of Sloane Platform Flips and tour the city’s mescal bars. Chicago’s got three mescal bars (Mezcaleria Las Flores, Masa Azul and La Mez), so get your agave on and try different kinds of the limey cocktail. Shop now

Photograph: Courtesy CC/Flickr/Daniel X. O'Neil

Enjoy a burger and a scoop at Bunny Hutch

Grab a burger, a scoop of ice cream and a soda at Bunny Hutch (6438 N Lincoln Ave), an old-timey diner in Lincolnwood, a quaint neighborhood just outside of Chicago.

Make it more fun: Mini golf and batting cages Take the kids and walk over to Novelty Golf and Games in a pair of Kids' Karin Clogs for a round of mini golf, or knock a few balls out of the park at the batting cages. Shop now

Humboldt Park
Photograph: Jaclyn Rivas

Hang around Humboldt Park

One of Chicago’s largest parks also boasts one of the most varied culinary selections in the city. Don’t forget to sample cultural eats while in the heart of the city’s Puerto Rican neighborhood.

Make it more fun:  Fit on the Kids’ Swiftwater Clogs and wade into the waters at the newly reopened Humboldt Park Beach. Shop now

Shoppers browsed a selection of handmade goods at the Renegade Craft Fair.
Photograph: Jaclyn Rivas

Shop at the Renegade Craft Fair

Head to The Hideout (1354 W Wabansia Ave) for the summer Renegade Craft Fair on June 25 & 26 and shop until you drop, with access to tons of stellar local artists and craftspeople selling housewares, jewelry, food and more.

Make it more fun:  Keep the creative energy flowing in a pair of Karin Floral Clogs and sign up for a woodworking workshop at Rebuilding Exchange (1740 W Webster Ave). Shop more

Chicago Sandblast ultimate frisbee tournament at Montrose Beach, 7/11/10
Photograph: Max Herman

Lay out on Montrose Beach

Hit the family-friendly Montrose Beach (4400 North Lake Shore Drive) just north of the city center for a more relaxing afternoon in the sun and sand.

Make it more fun:  Take the dogs! Slip on a pair of Sloane Platform Flips and walk with man’s best friend in this sandy, dog-friendly area of beautiful lakefront beach. Shop now


Stroll through the historic Graceland Cemetery

Tour the beautiful grounds of this historic cemetery (4001 N Clark St) and take in a wealth of history, including seeing the graves of famous Chicagoan architects like Daniel Burnham and Ludwig Mies van der Rohe.

Make it more fun:  Have a picnic in Graceland Arboretum, home to more than 2,000 trees, in a pair of Leigh Graphic Wedges. Shop now

Logan Square Farmers Market
Photograph: Wendell Remington

Stock up at a farmers' market

Dig out the recipe book before heading to the nearest farmers’ market like the Logan Square Farmers Market (3107 Logan Blvd)  to pick some great local produce and some beautiful flowers for a fun summer meal.

Make it more fun:  Order a CSA box from a local farm Plan your meals ahead by signing up for a CSA, short for community supported agriculture, and get supplied with weekly fresh, colorful produce. Slip on a pair of Karin Floral Clogs and prepare for a barbecue or two on the patio. Shop now

A busy Saturday afternoon at Gene's Sausage Shop in Lincoln Square.

Fill up at Gene's Sausage Shop and Delicatessen

Shop for Gene’s specialties like premium-grade, grass-fed certified organic beef or even fruit-shaped marzipan baskets.

Make it more fun:  Slip on a pair of Yukon Mesa Clogs and head to the rooftop, where you can get smoked sausages and bratwurst cooked on an open wood sausage grill. Shop now

Discover more fun activities

Garfield Conservatory
Photograph: Jaclyn Rivas

Explore Garfield Park

Mosey through the 185-acre park and check out the historic Golden Dome field house at Garfield Park (300 N Central Park Ave, 312-746-5100). Cool off with a dip at the pool or take a few swings with a friend on the tennis courts.

Make it more fun: Tread through Garfield Park Conservatory, one of the largest indoor conservatories in the world, and match your surroundings with a pair of Karin Floral Clogs. Shop now.

Maggie Daley Park

Play at Maggie Daley Park

Maggie Daley Park (337 E Randolph St, 312-742-3918) has a little something for everyone, including one of the most imaginative playgrounds in the city and first-rate views of the skyline.

Make it more fun: Send your little ones sparkling up the Maggie Daley rock wall in a pair of Kids’ CrocsLights Fire Dragon Clogs. Shop now

Oak Street Beach
Photograph: Kaitlin Hetterscheidt

Hang out at Oak Street Beach

Head over to this downtown beach for an unbeatable close-up view of the skyline and soak up some rays at one of the city’s most popular beaches, Oak Street Beach. (1000 N Lake Shore Dr, 312-742-5121)

Make it more fun: Slip on a pair of Leigh Graphic Wedges and have frozen drinks at the Oak Street Beach bar (1001 N Lake Shore Dr). Shop now.

Photograph: Katie Kullen

Explore Chicago's museum campus

Wander through several museums and an aquarium (1200 S Lake Shore Dr, 312-939-2438) in a single day. Be sure to turn around and check out the skyline! The campus boasts one of Chicago’s best city views.

Make it more fun: Be stylish and comfy in a pair of Sienna Flats and sign up for one of the many tours at Adler Planetarium, Shedd Aquarium or the Field Museum conducted by expert staff. Shop now.


Take a walking tour

Learn about Chicago’s iconic architecture with a tour from the Chicago Architecture Foundation (224 S Michigan Ave, 312-922-3432). When you take a tour by foot, you’ll get to experience how the locals live.

Make it more fun: Throw on a pair of Yukon Mesa Clogs and hop on a Segway to ride in comfort as you roll through Chicago. You’ll get to cover more ground and really see everything the city has to offer. Shop now.

Tall Ship Windy
Photograph: Courtesy CC/Flickr/Bart Heird

Climb aboard Tall Ship Windy

Head over to Navy Pier (600 E Grand Ave, 312-595-7437) with the whole family and travel like the pirates did, on the open sea—err, lake.

Make it more fun:  Slip on a pair of waterproof Swiftwater Clogs and take over Lake Michigan with your own captain with a private daytime sailboat rental from Chicago Sailboat Charters. Shop now.


Spend an evening at WhirlyBall

Hit one of 12 bowling lanes at WhirlyBall (1825 W Webster Ave, 773-486-7777) in Bucktown, where you can go for a strike (or, more realistically, a spare) while enjoying a full bar and food menu.

Make it more fun: Hop into a bumper car and take on an opposing team in a game of WhirlyBall—a combination of lacrosse, hockey and basketball. In your Yukon Mesa Clogs, you’ll have no trouble dominating on the court. Shop now

Chicago skyline from Promontory Point
Photograph: Courtesy CC/Flickr/JohnPickenPhoto

Take the Hyde Park History walking tour

Stroll around the beautiful Hyde Park neighborhood and take in all of the rich history the area has to offer. Start at the Hyde Park Historical Society (5529 S Lake Park Ave, 773-493-1893), which lives in a building that acted as a waiting room for cable car personnel during the 1893 World’s Columbian Exposition and head out on foot with your to check out some of the gorgeous historic architecture in the area.

Make it more fun: Head across Lake Shore Drive to Promontory Point and have a picnic while looking at one of the best views of Chicago’s skyline in the entire city. Afterwards, enjoy a delightful stroll along the Lakefront Trail in your Sienna Flats. Shop now

Green Music Festival brought a bike-powered stage and eco-friendly vendors to Wicker Park.
Photograph: Kaitlin Hetterscheidt

Attend the Green Music Fest

Spend a weekend at the Green Music Fest (between North Ave and Schiller sts) in Wicker Park, an annual street festival that celebrates sustainability and welcomes local and national bands to its stages.

Make it more fun: Get in on the fun by getting on a stationary bike and pedaling to generate electricity for one of the stages. If you’re sporting Yukon Mesa Clogs, you’ll be able to rack up some wattage in no time. Shop now. 

Lincoln Park Zoo Summer Camp
Photograph: Todd Rosenberg

Head to Lincoln Park Zoo

Trek out to the always free Lincoln Park Zoo (2001 N Clark St, 312-742-2000) and gawk at the animals in one of the best urban zoos in the entire country. 

Make it more fun: Channel your inner Monet by taking a couple of laps around Lincoln Park’s Caldwell Lily Pond. If you’re donning a pair of Isabella Sandals, your style will be as inspiring as the landscape. Shop now

Navy Pier
Photograph: Grace Allen

Hang out at Navy Pier

Stroll down Navy Pier (600 E Grand Ave, 312-595-7437) and take a ride on the new and improved Ferris wheel for some of the best views of the city. Enjoy carnival rides, games, performances and fireworks at night all summer long.

Make it more fun:  Make a splash in Kids’ Karin Clogs at the Chicago Children’s Museum. The flowing water playground is stocked with pulleys, wheels, pipes, boats and rubber duckies to make sure everyone has an awesome time. Shop now

Photograph: Jaclyn Rivas

Go on a walking food tour

Walk a mile or two on one of Chicago Food Planet’s walking food tours. Whether you want to explore a new neighborhood (you can pick from Gold Coast and Old Town, Bucktown and Wicker Park, Chinatown or Lincoln Park) and try all the eats or just want a fun weekend activity, you’ll get to try spots like Chiu Quon Bakery (1127 W Argyle St) and Sultan’s Market (2521 N Clark St)

Make it more fun:  Head to the Pilsen Food Truck Social, which brings in not only the city’s best food trucks, but great local art, retail and craft vendors. Get a taste of all the food trucks with sample tickets, drink some beer and shop around. Afterwards, enjoy a stroll in your Sienna Flats through colorful Pilsen. Shop now

Chicago Helicopter Experience

Take a helicopter tour

Enjoy the view from high above the skyscrapers on a helicopter tour of the city, provided by Chicago Helicopter Experience (2420 S Halsted St, 855-414-8687). Tours take off from a small heliport in Bridgeport, so you don’t have to go far to get sky high.

Make it more fun:  Spring for the private helicopter tour and get ready to soar above Lake Michigan with one of your closest friends. Make sure to bring a pair of Yukon Mesa Clogs to wear when you land safely back on the ground. Shop now

Chicago Architecture River Cruise

Go on an architecture cruise

You can almost always find an architecture cruise to jump on in Chicago in the summer, but the Chicago Architecture Foundation (224 S Michigan Ave, 312-922-3432) tour is among the best. Explore different styles of architecture from the river. Line up early and be among the first people to board to ensure you get an open-air spot on the boat for plenty of photo ops.

Make it more fun: Slip on a pair of Swiftwater Clogs and get closer to the water when you rent a kayak and traverse the Chicago River with Urban Kayaks. Shop now

Photograph: Jaclyn Rivas

Discover public art

Take an easy walk through the Loop to see a Miro (69 W Washington St), Picasso (50 W Washington St), Calder (Dearborn and Adams sts) and a Dubuffet (100 W Randolph St), among others.

Make it more fun:  Venture off the beaten path in a pair of Sienna Flats and check out “Statue Stories,” where he likes of Abraham Lincoln, Leif Erikson and even Hebe tell you how they got to Lincoln, Humboldt and Grant parks, respectively. Shop now

The 606
Photograph: Zach Long

Take a trip on the 606

Chicago’s new trail winds through some of the city’s hottest neighborhoods, connecting Logan Square, Humboldt Park, Wicker Park and Bucktown. Hop on and off the 606 (773-661-9172) to explore nearby shops, restaurants, bars and more in the area. You can easily access the 606 from the Western and Damen Blue Line stations. Stroll down the path to uncover public art and a sense of nature in the heart of the city. 

Make it more fun: Slip into a pair of Karin Floral Clogs, and catch even more of the trail in record time by bike. Don’t worry, there are plenty of Divvy stations nearby if you don’t have your own. Shop now

Tilt gives visitors a unique view of the city from the top of the John Hancock Center.
Photograph: Martha Williams

Take in the views at 360 Chicago

Hop in the elevator and zoom up to the 94th floor of the John Hancock Building (875 N Michigan Ave, 312-751-3681), where you can take in stunning views of the city, from the lake to the Loop and beyond.

Make it more fun: Slip into your comfy Sienna Flats, put on a brave face, and step into Tilt!, which gives you a whole new perspective on the city from 1,000 feet up. The first of its kind, Tilt! is an experience that actually moves the visitors on an angle to feel like they’re hovering above the city. Shop now

Find something great to do in Chicago this week
Photograph: Jason Little

Meander through Millennium Park 

Taking selfies with the Bean or spreading out on the lawn at Jay Pritzker Pavilion (201 E Randolph St) isn’t just for tourists. Spend an afternoon in the heart of the city exploring public art and splashing in Crown Fountain.

Make it more fun: Catch a free dance lesson in your Isabella Sandals at SummerDance. Held throughout the summer, this free event teaches Chicagoans how to dance everything from the cha-cha to the waltz. Shop now

Photograph: Jaclyn Rivas

Speed through town on a water taxi

Cabs in the summer are a stuffy bore—skip the road and take a Chicago Water Taxi (400 N Michigan Ave, 312-337-1446) to navigate the city through the river.

Make it more fun: Take the taxi all the way to Chinatown, then hop out and meander through one of Chicago’s best neighborhoods on foot in a pair of Karin Floral Clogs. From great restaurants to tea shops, KTV lounges, bubble tea spots, public art and more, there’s plenty to uncover in Chinatown. Shop now



Photographer Nick Ulivieri captured these images of the Wrigley field construction from a helicopter.
Photograph: Nick Ulivieri

Take a tour of Wrigley Field

See the ivy up close and personal on a guided tour of Wrigley Field’s (1060 W Addison St) hallowed grounds, and learn about the park’s history. 

Make it more fun: There’s no better way to enjoy Wrigley than by sitting in the bleachers on game day while eating a hot dog. Get tickets to cheer on the team in what’s sure to be a momentous season. Step into a pair of Yukon Mesa Clogs, grab your peanuts and Cracker Jacks, and root, root, root for the Cubbies! Shop now


Happy Lobster
Photograph: Jaclyn Rivas

Escape the office during your lunch hour

Enjoy Chicago’s best season by heading out of the office and exploring the Loop on your lunch hour. Take in the city’s best architecture, swing by the lakefront, stroll along the river, and enjoy those rare days full of sunshine that every Chicagoan lives for.

Make it more fun: Head to Daley Plaza (50 W Washington St) for loads of great offerings from local food trucks. This summer the square is home to not only Picasso’s most famous public work but also some of the best bites in the city. In Sienna Flats, your feet will be happy to take you from counter to counter to taste offerings from across the city and around the world. Shop now


Photograph: Jeremy Atherton

Stroll down the Riverwalk 

The recently renovated Riverwalk makes for a great place for an evening stroll after work or a chill spot to spend a few hours on a Saturday. Hop on the riverfront path at East Upper Wacker Drive and North Michigan Avenue, and relax on the steps and take in the view, or pop into one of the restaurants and bars along the river for an easygoing bite and drink.

Make it more fun: Slip into your waterproof Swiftwater Clogs, and rent a kayak to paddle through the river. See the whole city from a new perspective as you make your way through the Loop and up the north branch of the river on a guided tour. Shop now

Ravinia Kids Concerts

Catch an outdoor concert at Ravinia

The always-impressive summer music lineup at Ravinia (418 Sheridan Road) has something for everyone, from classical nights by the Chicago Symphony Orchestra to pop, jazz and country music, plus concerts for the kids.

Make it more fun: Pack a picnic and lay out blankets for the night while listening to your favorite music. Concertgoers at Ravinia take this very seriously, so step up your spread! Slip into your comfy Sienna Flats and kick back for a night of music under the stars. Shop now


Families flock to the riverfront Ping Tom Park in Chinatown for screenings under the stars.
Photograph: Courtesy Chicago Park District

Enjoy a picnic in the park

Pack your best basket of food—or let some of our favorite restaurants and shops pack one for you—and sprawl out on a blanket to bask in summer nights in the city with a view.

Make it more fun: Put on your coziest Sloane Platform Flips, and feast on your picnic while watching a movie in the park. All summer long, the city offers tons of free screenings, from ’80s classics to the latest hits, so plan your schedule and get there early to score a great spot on the lawn. Shop now


Kids and Kites Festival, Cricket Hill

Spend an afternoon on Cricket Hill

Spend the day playing games and soaking up the sun on this grassy knoll in Lincoln Park (2045 N Lincoln Park West).

Make it more fun: Have the kids slip on a pair of playful CrocsLights Fire Dragon Clogs, and join Chicago families at the annual Kids and Kites Festival on May 7. The festival is free—to participate, just pack your kite and watch the sky fill with a multitude of colors. If you miss the festivities, you can always fly your own kite from this prime location on another summer day. Shop now


More to explore