Find your fun in Chicago this summer

Explore Garfield Park

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.

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

Hang out at Oak Street Beach

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.
 

Explore Chicago's museum campus

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

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.

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. 

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. 

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. 

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. 

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. 

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. 

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. 

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. 

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. 

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

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

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

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

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

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

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

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

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

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