We devote thousands of hours of research to help you get Big Travel with Small Money. You support us by signing-up for credit cards through partner links which earn us a commission. Here’s our full Advertising Policy.
Chicago is a great city to visit. There are lots of great restaurants and bars, beautiful outdoor parks, and tons of museums. Plus, it has so much great architecture, and it’s awesome to see a city prioritize the art of creating homes & buildings. I spent a few years living in Chicago, and here are my top 5 things to do.
The Million Mile Secrets team will be in Chicago October 19-21, 2018 for the Chicago Seminars. Come stop by and say hello to us!
5 Best Things to Do in Chicago
1. Architecture Boat Tour
The architecture boat tour is my favorite activity to do in Chicago. You’ll cruise around the Chicago River and get a historical tour of the buildings you see. A must for architecture buffs! Check Groupon for discounts on tickets.
2. Experience Deep Dish Pizza
Deep dish pizza is like no other pizza. One slice is a meal in itself. Chicagoans can get into heated arguments over which pizzeria makes the best pizza. Reader Michael swears by Lou Malnati’s, and his mom even ordered a few to be shipped to his college town because he missed it so much.
3. The Skydeck
The Skydeck, located in the Sears (Willis) Tower is expensive, but worth doing once. Tickets are ~$24 for adults. They have glass boxes that extend 4 feet out and are freaky to stand on.
4. Chicago Style Dog and Italian Beef
Chicago’s known for not only pizza, but hot dogs, too! You won’t any find any ketchup on these dogs, though. The hot dog is topped with classic yellow mustard, diced white onions, sweet pickle relish, a dill pickle spear, fresh tomatoes and pickled sport peppers.
Chicago has a lot of really great museums. The Field Museum has the Lions of Tsavo, which are the famous man eaters from the Val Kilmer movie “The Ghost in the Darkness.” The Museum of Science and Industry is the last major building remaining from the 1893 World’s Fair. If you have kids, they may love a trip to the Chicago Children’s Museum. Team member Jasmin took her kids there, and they had a blast!
What are your favorite things to do in Chicago?