Best Things to do When Visiting Chicago

Chicago is such a fabulous city! It’s full of culture, stunning architecture, delicious food and entertaining sports teams. The Windy City is a top destination that you should visit May - September. Summers in the city are lively and will fill your travel cup!

As you plan your trip to the midwest, take note of my top 5 places to see during your stay. Keep reading to the end to see which bonus places I had to include, just in case you have extra time to explore.

5 Places to Check out During Your Visit

  1. Learn about the unique buildings along the Chicago River during the Chicago River Boat Architecture Tour. During the guided tour, you will take in the stunning scenery of the city and information about the different styles of architecture. Over 50 buildings are highlighted. The guides are extremely knowledgable and you’ll be surprised with all of the information that you learn during the tour. The excursions begin just about every hour between 10 am - 8 pm and last 90 minutes. If you decide to begin your tour on Navy Pier, plan on a 2 hour tour. Tickets begin at $49 for adults and $30 for children ages 7-12. Those 6 and under are free. If you are traveling in the warmer months, this is a must-do activity!

  2. The Windy City is full of incredible museums that each offer a unique experience. If you are short on time and can only visit one museum, purchase tickets to go to the Art Institute of Chicago. There are many pieces of well-known pieces of art that line the walls of the museum. Be sure to check out the rotating exhibits. Van Gogh and the Avant-Garde: The Modern Landscape runs through September 4, 2023. Ticket prices begin at $34.

  3. Visiting a large city, calls for a having a drink at a fun rooftop bar. Visit Cindy’s Rooftop, which is located on the 13th floor of the Chicago Athletic Association. The Open-air terrace provides stunning views of Millennium Park and more! The cocktails at Cindy’s are sophisticated and unique. Reservations are available 30 days in advance. Take my advice and book those reservations as soon as you can. Note that reservations are for 2 hours or less.

  4. Head on over to Wrigleyville to catch a Chicago Cubs game! Wrigley Field is a classic baseball field that is incredible for all to experience. Any seat in the stadium is a good one. Sitting in the bleachers is a lot of fun, too! Bleacher seats are first come, first served. Stop by the statue of Harry Caray and visit restaurants in the area before and after the game. The neighborhood comes alive on game days!

  5. Enjoy the scenic Chicago Lakefront Trail by foot or bike. This path is a great way to take in views of Lake Michigan and the stunning city of Chicago. The trail is 18.5 miles long. Enjoy any part of the pathway.

A Few Bonus Places

  1. Enjoy the warm weather and listen to live music at Ravinia. Tickets for concerts are available beginning of June - beginning of September. There are many musicians that you are familiar with that perform at this outdoor venue.

  2. See the start of Route 66 in downtown Chicago. This well-known route began in 1926 at the corner of Jackson Boulevard and Michigan Avenue. The famous route ends on the Santa Monica Pier in California. Route 66 was created to carry heavy traffic and many people remember it for the historic small towns that popped up along the highway.

If you plan on really making the most of your visit, I suggest purchasing a Chicago Citypass. For $104 per ticket entrances are included to the following experiences; the Art Institute of Chicago, Shedd Aquarium and Skydeck Chicago and two of the following: the Field Museum, the Museum of Science and Industry, 360 CHICAGO Observation Deck, the Adler Planetarium or Shoreline Sightseeing Architecture River Tour. The Citypass is the way to go if you plan on seeing multiple attractions.

What is a site that you suggest seeing in Chicago?

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