4 Fun Things to Do in Chicago This Summer

things to do in Chicago

Chicago is one of the most popular destinations in the US, with tourists and locals alike flocking to the bustling city streets to soak up the sights and sounds. Known as the ‘Windy City,’ Chicago hosts an eclectic mix of world-class museums, restaurants, art, comedy, sports, and music. If you’re visiting the city this summer and are looking for some interesting and entertaining ideas, look no further! Chicago is my hometown so I gathered for you some of the best things to do in Chicago this summer.

things to do in chicago, navy pier
Navy Pier

1. Spend the Day at Navy Pier

Navy Pier is Chicago’s iconic lakefront destination and it plays host to a number of popular restaurants, shops, boat tours, and much more. Originally created to be nothing more than a freight dock, Navy Pier has evolved over the decades into the hotspot that it is today. Navy Pier now features a children’s museum, a theater, a seasonal beer garden, shopping, restaurants, bars, and even some thrilling rides. Let’s not forget to mention Navy Pier also has one of the best views of Lake Michigan and the Chicago skyline!

Navy Pier offers a bunch of free events throughout the year, including cultural events, art exhibits, outdoor movies, and more. Many cruise operations also run out of Navy Pier. Speedboat tours, dinner cruises, architectural cruises, and sightseeing tours start here. Be sure to ride Navy Pier’s infamous icon, the Centennial Wheel, which takes you up 200 feet for an amazing view of the shoreline.

2. Take a Street Art Tour 

Chicago has long been recognized for its passion of street art. Many visitors flock to visit such eye-catching and unique creations. The city is full of jaw-dropping urban art and the best way to see it is by booking a unique street art tour. Guides will not only show you some of Chicago’s most memorable urban art, they will also take the time to explain the meaning and history behind it. Artists, photographers, and social media fans will love touring and sharing photos of Chicago’s street art scene.

things to do in chicago
The Wrigley Building and Chicago River

3. Cruise around the City via Motorcycle

Cruising around any city on a motorcycle is one of the best ways to take in the sights. In Chicago, there are different local routes and rides, both long and short, to get a comprehensive view of everything the city offers. To add to this, there are other exciting motorcycle related events such as the Chicago Motorcycle Show. It’s easy and affordable to rent a motorcycle in Chicago too, no matter what kind of tour or trip that you have planned. Just be sure to wear appropriate clothing and don’t forget your helmet!

4. Delight in Chicago Food

While Chicago is well-known for its famous deep dish pizza, the Windy City actually has a number of local delicacies and food spots that will amaze you. Booking a food tour is a fun way to try them all, devouring Chicago classics like hot dogs and Italian beef sandwiches. Here’s a quick list of our most notable foods and/or food establishments:

  • Pizza – Giordano’s, Lou Malnati’s, Pizzeria Due/Pizzeria Uno, Pequod’s, Pizano’s, Gino’s East
  • Italian Beef – Portillo’s, Al’s Italian Beef, Mr. Beef
  • Hot Dogs – Portillo’s, Superdawg, Gene & Jude’s
  • Popcorn – Garrett’s popcorn (try the Chicago mix of caramel and cheese popcorn!)
  • Desserts – Frango mints (Macy’s), Eli’s Famous Cheesecake, the Doughnut Vault
things to do in chicago
Cloud Gate, aka “the Bean”

Other notable sightseeing in Chicago:

  • Take a cruise along the Chicago River
  • See “the Bean” (officially known as Cloud Gate) and beautiful Millenium Park
  • Walk the Chicago Riverwalk
  • Visit the Brookfield Zoo or the Lincoln Park Zoo (It’s free!)
  • Shop along Michigan Avenue
  • Walk to Buckingham Fountain and see beautiful Lake Michigan
  • Visit the Skydeck on the 103rd floor of the Willis Tower (once known as the Sears Tower)
  • Spend a day touring amazing museums (most notably The Museum of Science and Industry, The Field Museum, and The Art Institute of Chicago)
  • Tour the Chicago Botanical Garden
  • Catch a Cubs game in historic Wrigley Field
  • Visit one of Frank Lloyd Wright’s homes (specifically his home and studio in Oak Park or the Robie House in Hyde Park)

Exploring Chicago during the summer months is a fantastic way to spend a week. Boats are out on the lake, outdoor dining resumes, and the city comes alive again after our long, cold winters. There is so much history and culture here that you’d need weeks to see it all. However, this short list of things to do in Chicago should be a great start for your epic urban vacation!

Happy Travels!


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