Our 10 Favorite Summer Activities in Chicago

Here’s how to make the most of the summer season in the Windy City.

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Every April, my sister Colleen and I talk about moving to a warmer climate, as our winters in Chicago seem to last forever. But when May hits, the birds start chirping again, the trees start to fill in and the memorable smells of summer return – and we fall in love all over again. Here are our favorite ways to enjoy Chicago in the summer.

1. Electric Boats and Cycle Boats

Photo by: Chicago Electric Boats

Chicago Electric Boats

Lake Michigan and the Chicago River are a couple of places where we love to hang out in the city during the summer. Bring your cooler and hop onto one of the electric boats that cruise along the legendary Chicago River. This experience is a unique and an environmentally friendly way to see the beautiful sites and architecture of Chicago. You can drive your own boat, or hire someone to drive you around the river. We love going on an evening cruise and watching the fireworks, which take place every Wednesday and Saturday night in the summer, right off the Chicago River by Navy Pier. Also, check out the brand-new Chicago Cycle Boats. It’s BYOB or BYOF (bring your own food) as well, and fun with a large group of people. Pedalers sit on comfortable bike seats at a table as they pedal at their own pace on the Chicago River. Riders can sit or stand while they enjoy the view. The bikes are electric with a captain guiding the way, so pedaling is fun but entirely optional.

2. Shopping and Champagne

Photo by: Randolph Street Market

Randolph Street Market

Randolph Street Market is located in the Fulton Market area in the West Loop. People come from all over to shop and find the best in vintage clothing and antique treasures. You’ll feel like you’re in your own episode of Flea Market Flip. Half the fun is negotiating, so bring cash.

Photo by: Anthony Tahlier

Anthony Tahlier

After you've gotten your shopping high, stop in at one of our favorite places, RM Champagne Salon. Tucked away down an enchanting alley off of Green Street in the heart of the West Loop, RM Champagne Salon offers one of the most delightful atmospheres in the city, with a dinner menu inspired by Parisian comfort food. Sit outside and enjoy the bistro lights that flicker over the cobblestone patio and enjoy the ultimate urban dining experience.

3.Wrigleyville/Chicago Cubs Game

Photo by: Chicago Cubs

Chicago Cubs

Chicago loves their Cubs, and we’re still feeling the excitement of our World Series win in 2016. So, while we always recommend experiencing a ball game while visiting Chicago, you can also take a tour of Wrigley Field or even enjoy an outdoor concert. There’s nothing better (besides watching the game) than sitting in the bleachers and taking in the view from the infield, listening to Jimmy Buffet, Pearl Jam, Luke Bryan or Billy Joel (all of whom are coming to Chicago this summer). Wrigley Field also has a new plaza located just outside the ballpark called Gallagher Way. In the summer, they have farmers markets, movie nights and musical performances on Thursdays.

4. Street Festivals

Photo by: The Trip Sisters

The Trip Sisters

If there’s one thing we know in Chicago, it’s food and street fests. They take place every weekend in the summer all throughout the city. Find a full guide of all the events here, or check out a few of our top picks:

- Chicago Gourmet: The Chicago Gourmet (pictured above) actually takes place in September, but in our opinion, it’s one the best food and wine festivals in Chicago. So, mark your calendars and buy your tickets early since this fest sells out quickly.

5. 360 Chicago

Photo by: The Trip Sisters

The Trip Sisters

If you like seeing the sites from 1,000 feet in the air, you’ll love 360 Chicago. It’s located on top of the John Hancock Center and gives you a 360-degree view of Chicago’s beautiful skyline. If you’re feeling daring while you’re there, you can also check out TILT. As the name implies, this thrill ride tilts you at a 30-degree angle high above the city for an unforgettable view. 360 Chicago is also a nice place to have a drink before dinner, or if you’re in town on a Friday night, bring your friends and stay for trivia. Find the full line-up of activities on their website. It’s also a great spot to watch the fireworks every Wednesday and Saturday, and of course the Air & Water Show in August.

Tilt! at 360 Chicago
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6. Ravinia

Photo by: Ravinia Festival

Ravinia Festival

Ravinia Festival is the oldest outdoor music festival in the United States, with a series of outdoor concerts and performances held every summer from June to September. It’s a spectacular way to take in the sounds of great musical acts with more than 140 shows to choose from this year. The Ravinia concert series offers every type of music from Yo-Yo Ma to John Legend to The Chicago Symphony Orchestra. Located about 25 miles from Chicago, you can drive, but we recommend taking the train in from the city. Bring your own chairs (or you can rent them) and food and make it a picnic. Feel like being waited on instead? Have dinner at one of their brand-new restaurants that just opened this summer, The Tree Top, Park View and Lawn Bar.

7. Vavoom Pinups

Photo by: Vavoom Pinups

Vavoom Pinups

Vavoom Pinups is a complete head-to-toe photography experience that captures your inner pinup girl. This activity is a little outside of the box, but it’s one we highly recommend trying with a group of friends or solo. Get ready to be pampered as you step back in time to 1940s Hollywood and get all “dolled up” for your photo shoot. This is one experience we tell all of our girlfriends to do when visiting Chicago. It’s perfect for a girls’ getaway weekend or bachelorette party.

8. Helicopter Tours

Photo by: Chicago Helicopter Experience

Chicago Helicopter Experience

See Chicago from a bird’s-eye view as you soar through the city with Chicago Helicopter Experience. Take a daytime tour and see iconic skyscrapers like Willis Tower and the John Hancock, then head down to Wrigleyville and take in a Cub’s game from the sky. Learn all about Chicago as your pilot narrates the history while you enjoy the views. It’s a breathtaking experience and perfect for Facebook and Instagram posts. They also have an evening tour of the city that departs after sunset and includes a cool glass of champagne. Enjoy the sparkling lights below as you fly through the night sky.

9. iO Theater

Photo by: iO Theater

iO Theater

Chicago is well known for comedy theater. We proudly claim the likes of Tina Fey, Amy Poehler, Stephen Colbert, Chris Farley and Neil Flynn, who all learned the art of improv right here in Chicago. They trained at the famous iO Theater in the Lincoln Park neighborhood (formerly known as Improv Olympics), along with many other Saturday Night Live alumni like Jason Sudeikis, Seth Meyers and Cecily Strong. If you want to catch both iO alumni and new and up-and-coming comedy acts this summer, be sure to visit the Bentwood Comedy Festival, August 10 through 19. The iO Theater also has two full bars, a beer garden and a kitchen where you can relax and have a casual American cuisine dining experience before or after the show.

10. Museums

Photo by: National Museum of Mexican Art

National Museum of Mexican Art

There’s no shortage of must-visit museums throughout Chicago, but here are a couple of our favorites:

The Museum of Science and Industry: This is one of our favorite museums in Chicago and a great adventure for all ages. Among the museum's exhibits are a full-size replica of a working coal mine, a German submarine U-505 captured during World War II, a 3,500-square-foot model railroad and the command module of Apollo 8. Be sure to check out Science Storms and try to change the course of a 40-foot tornado as well as see a 20-foot Tesla coil. Give yourself plenty of time here as there is so much to see and do. The museum is located in the Hyde Park area about 15 minutes from downtown.

National Museum of Mexican Art: For an enriching cultural experience this summer, check out the National Museum of Mexican Art (pictured above). Located in Chicago’s Pilsen neighborhood, this museum showcases the beauty of Mexican art and culture. The museum is also currently hosting several unique summer exhibits through August 19, such as Arte Diseno Xicago, which includes life-size bronzes, and Best of Yollo, which features a teen-curated exhibition of artworks by young artists. After the museum, be sure to stop by 5 Rabanitos for a little Mexican cuisine.

As you can see, there is so much to do in Chicago. Yes, it’s cold in the winter, but experiencing a Chicago summer makes it all worthwhile! Follow us @theTripSisters for more of our adventures.

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