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Top things to do in Chicago

See all 167 things to do in Chicago

What to Do in Chicago

AARP® Travel Center Powered by Expedia® is here to help you take your Chicago holiday to places you'll remember for years to come. With fascinating historical tours to stunning aerial tours, there is something available that is most likely on your bucket list, or that you can't wait to show your friends. We've put together a list of activities and outings that are certain to elevate your vacation in Chicago and create lasting memories.

Let Us Guide Your Next Adventure

  • The activities in Chicago are among the best. We have 102 things to do in Chicago, and you can make them yours starting at just $8. AARP members can get their favorite activities and day trips for significant savings, and you will still have enough cash for a luxurious Chicago hotel room or a rental car in Chicago while you’re in town.
  • Our list includes plenty of choices historically based outings and excitement. With private and full-day tours that allow you to experience a rare side of the city like a Guided Tour of Legendary Chicago Sports Venues to unique ways to see a lot of what Chicago is popular for like Hop-On Hop-Off City Tour, you'll have to plan another Chicago flight or two to have the time to do all the activities you want. Go through our review section if you need a little advice on what which activity to go on.

Book Your Chicago Adventure Today!

From excursions that provide you an opportunity to see Chicago as few tourists do to countryside tours with spectacular views, you may be motivated to go on a trip like this every chance you get. Isn't about time that you start making the most out of your well-deserved vacation? You have the opportunity to enjoy more, see more, and do more on your vacation to Chicago with the AARP® Travel Center Powered by Expedia®. Book your trip today, and get ready for your next Chicago vacation to be an adventure!