We highly recommend a river architecture tour if it's your first time visiting Chicago! Bob took Joanna on one during her first trip to Chi town in October 2021 and she loved it! It's such a fun way to see the city. There are several companies that offer the tour. We've done both the Wendella and the Chicago Architecture Center tours.
Another of Joanna's favorites in Chicago is the Shedd Aquarium. Check out the sharks, sea otters and don't forget about the arapaima fish!
The Field Museum of Natural History is home to the famous T-Rex, Sue! Explore interactive displays on natural history, ancient civilizations, gemstones, wildlife, and dinosaurs.
The Field Museum is right next to the Shedd Aquarium if you want to see both in one afternoon!
The famous Riverwalk is a beautiful path along the Chicago river. It's a nice place to take a leisurely walk or stop into many of the riverfront restaurants for a drink or meal.
Please note that most access to the riverwalk is via stairs. There are other accessible entrances. Here is a map for ADA compliant ramps: https://www.chicago.gov/city/en/sites/chicagoriverwalk/home/accessibility.html