Top 10 Places to Visit in Chicago
Before you call our expert reservation specialists to book your trip, finalize your itinerary with all of the places you want to go in and around Chicago. If you need some inspiration, check out our top 10 recommended attractions, restaurants, and more below:
1. Green Mill Jazz Club
This lounge is a hot spot for jazz, with more than 100 years of history behind it. Enjoy delicious drinks, performances by skilled jazz musicians, slam poetry, and a 1940s vibe.
Address: 4802 N Broadway, Chicago, IL 60640
Phone: (773) 878-5552
2. Woolly Mammoth Antiques and Oddities
If your group is feeling adventurous, check out this strange antique shop. It features wall-to-wall displays of taxidermy, used hearing aids, loose teeth, lice powder, and more.
Address: 1513 W Foster Ave, Chicago, IL 60640
Phone: (773) 989-3294
3. Gullivers Pizza
You can’t leave Chicago without grabbing a slice of pizza. For a pizzeria that’s truly out of the ordinary, try Gullivers Pizza, which is packed with fine art, statues, and mouth-watering Italian dishes.
Address: 2727 Howard St, Chicago, IL 60645
Phone: (773) 338-2166
4. Secret Agent Supply Co.
Ever wanted to be a secret agent? Chicago has an entire store dedicated to gadgets, supplies, disguises, and more that spies need to succeed. Proceeds from your purchase go to the 826Chi, a non-profit that helps kids develop their writing skills.
Address: 1276 N Milwaukee Ave, Chicago, IL 60622
Phone: (773) 772-8108
5. Big Joe’s
What could be better than a neighborhood dive bar? A neighborhood dive bar with turtle racing! Visit Big Joe’s to see which turtle is slow enough to win the grand prize.
Address: 1818 W Foster Ave, Chicago, IL 60640
Phone: (773) 784-8755
Right photo Credit: Thrillist, Sean Cooley
6. Wrigley Hostel
If you’re traveling with a big group, consider staying in dormitory-style lodging like the Wrigley Hostel. They host trivia nights, movie showings, and pub crawls, and you can play games like ping pong or darts in their community room.
Address: 3514 N Sheffield Ave, Chicago, IL 60657
Phone: (773) 598-4471
7. Music Box Theatre
Since 1929, the Music Box Theatre has entertained movie lovers and cinephiles. Add this historic theatre to your itinerary for independent, foreign, and cult classic film showings.
Address: 3733 N Southport Ave, Chicago, IL 60613
Phone: (773) 871-6604
8. Magnificent Mile
For the shoppers in your group, add the Magnificent Mile to your list of must-sees. This stretch of Michigan Avenue is lined with high-end stores such as Lord & Taylor, Neiman Marcus, Saks Fifth Avenue, and more.
Address: North Michigan Avenue, Chicago, IL 60611
9. The 606
This former industrial rail line is now a nature trail and park for the public. The 606 is an excellent place to bike, run, or walk on a sunny day. You can even enjoy snowshoeing and cross-country skiing here in the winter!
Address: Chicago, IL 60647
Phone: (312) 742-4622
10. Wrigley Field
As the second-oldest MLB ballpark in the U.S., this baseball stadium is as rich in history as it is in local color. Come to see the Cubs take on one of their rivals, or take a tour of the stadium to learn more about the history of the team and the sport.
Address: 1060 W. Addison St., Chicago, IL 60613
Phone: (773) 404-2827
312-392-0239
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