Things To Do
The Bean at Millennium Park
This is the iconic Chicago landmark, colloquially named "The Bean" but officially named Cloud Gate. It is located in Millennium Park, which is on the lakefront of Chicago's downtown Loop. You can take the Chicago CTA train (there are multiple color lines - use Google Maps to guide you) to the State/Lake stop, which is approximately 2 blocks away from the park.
Naperville Riverwalk
Something a little closer to the hotel. Cute downtown area of Naperville. Full of lots of fun little shops and restaurants!
Wrigley Field
We went to our first Cubs game over a decade ago and never leave Wrigley disappointed. There is a Cubs home game on 9/12/25 at 1:20pm. Friday day games are awesome, because it is much less rowdy, much less busy, and there is way more seating at the surrounding restaurants/bars.
Au Cheval
Calling all foodies! Best burger joint in Chicago (yes, I'll bet you). Plan for a minimum 2-3 hour wait because they do not take reservations. There are multiple bars in the area (this is West Loop), so I'm sure you'll find something to do in the meantime!
The Chicago Theatre
The iconic Chicago Theatre can be found on the State/Lake stop of the Chicago CTA Train. The theatre sits right next to the bridge that leads to River North, which is full of fun restaurants and beautiful buildings. The Chicago River flows through downtown Chicago, so the views are incredible. The theatre is also a 2 block walk from Millennium Park and Cloud Gate (the Bean)!
Lincoln Park Zoo
Free zoo located close to downtown Chicago. Worth a stroll near the lakefront.
Mr. Beef
This is the inspiration for "The Bear". The restaurant is located in River North, which is a beautiful neighborhood to wander.
Chicago River Boat Architecture Tours
There are multiple companies that offer these tours. I would look into each and see who offers the best price. The cruise will take you down the Chicago River and give insight into the history of the city.