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7 Fun Things to Do in Chicago in the Summertime

In 2022, Chicago was named the “Best Big City in the US” for the sixth year in a row by the Conde Nast Traveler Readers’ Choice Awards. This was due to Chicago being a world-class travel destination with a vibrant history, cultural institutions, and world-class restaurants.

If you’re looking for things to do in Chicago during the summertime, it’s easy to get overwhelmed by the sheer volume of options. To plan the best summer vacation, you’ll need to learn where to go to get the most out of your visit.

Keep reading this guide to learn seven fun things to do in Chicago during your summer vacation!

1. Attend a Summer Festival

Festival season is what makes summer in Chicago a truly unique experience. First, you’ll be able to find plenty of street markets with live music and street food vendors. Maxwell Street Market and the Suenos Music Festival are popular events.

Also, you don’t want to miss the most famous festivals in Chicago, which include:

  • Grant Park Music Festival
  • Millennium Park Summer Music Series
  • Chicago Friday Night Flights
  • Lollapalooza
  • Chicago Blues Festival
  • Windy City Smokeout
  • Taste of Chicago

Finally, June is Chicago Dance Month, which features an entire month of dance from various genres performed all over the city.

2. Get Out on the Water

A Chicago vacation isn’t complete without spending some time on the water. The Chicago River flows past some of the city’s most amazing restaurants, buildings, and river walks. You’ll be able to see it all close up and personal when you take a sightseeing cruise.

You can find plenty of sunset cruises from the Navy Pier to enjoy Lake Michigan during the long summer nights.

If you want some freedom, consider renting a canoe, paddleboard, or jet ski to take in the scene on your own.

3. Visit the Navy Pier

The Navy Pier is one of the most popular attractions in the city and for good reason. There are so many activities going on at the pier during the summertime. To begin with, the Navy Pier is where you’ll find all the best lakefront cruises.

You can also enjoy a ride on the Centennial Wheel. It offers 360-degree views of the city and measures almost 200 feet high. The Centennial Wheel came to Chicago in 1893 during the World’s Columbian Exposition.

Summer fireworks are another popular event you’ll find at the pier throughout the summer. Fireworks displays are on Wednesday and Saturday nights from Memorial Day through Labor Day.

Finally, bike tours, movies, dancing, free live music, and a waterfront beer garden will round out the evening.

4. Spend a Day on the Beach

Chicago has mile after mile of beautiful sandy lakefront beaches to enjoy. You can lounge at Foster Beach and enjoy a calm day relaxing or rent a bike.

Rainbow Beach has some of the most breathtaking views of the Chicago skyline. It’s also called Rainbow Beach for a good reason. You’ll find dunes with a rainbow of colors all along the shoreline. These dunes are an ecologically important area of Chicago and well worth the visit.

Rainbow Beach also has amenities like:

  • Fitness center
  • Gym
  • Multipurpose rooms
  • Community gardens
  • Basketball and tennis courts
  • Two playgrounds

Or, if you want to spoil yourself, visit the Shore Club Chicago and reserve a cabana at North Avenue Beach.

There are also plenty of kayak or paddleboard rentals to choose from, no matter which beach you visit.

5. Visit an Escape Room

During your trip to Chicago, you’ll definitely have those days when you need to get out of the sun. It’s the perfect chance to experience a Chicago escape room.

It makes for a unique and memorable experience, so you’ll want to add it to your list.

You can visit The Great Escape Room, voted one of America’s best escape room experiences. Try the infirmary escape room and solve clues to stop a deadly virus. Or, you can attempt to escape from the president’s bunker in under 60 minutes.

Click here for escape rooms to find the perfect experience for your summer vacation.

6. Stop by the Local Farmer’s Markets

From May to October, you’ll find dozens of fresh markets for shopping. These markets aren’t just for locals to grocery shop at either.

You’ll find fresh products and unique food vendors selling meat, veggies, and fresh fruits. You can even find tasty treats like pastries made to order at popular markets like Logan Square Farmer’s Market.

In addition, Maxwell Street Market serves up delicious Mexican food and a wide range of seasonal produce. After you eat, you’ll have fun finding bargains on clothes, furniture, household items, and antique collectibles.

7. Take a Tour

Going on a tour is one of the best ways to take in the city and get the most out of your visit. Not to mention, summertime tours allow you to see things you may not be able to see at other times of the year.

You can go on Free Tours by Foot and learn about the iconic architecture that makes up the city. These tours offer food, bike, and walking tours with no upfront cost, and you can decide at the end how much the tour was worth.

It’s much like a “pay what you want” type of touring experience that’s great for anyone on a budget.

Chicago Walking Tours is another great option that takes you downtown, focusing on the interiors of buildings. You’ll get the inside scoop on specific architectural elements and see unique hidden details of buildings most people never notice.

Don’t forget to go on a bike tour to explore the unique Chicago neighborhoods as well as the rest of the city. Weird tours are also fun, taking you through haunted houses where you’ll hear spooky stories.

Enjoy These Fun Things to Do in Chicago

Now that you have a list of the top seven things to do in Chicago, you can start planning your summer vacation.

Chicago has so much to offer, so keep researching to find more events you might be interested in. Don’t be afraid to walk around downtown to see where the day takes you. You’ll be sure to find something fun and unexpected.

For more exciting lifestyle and travel tips, make sure to check out the rest of our blog today!

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