If your here long enough take the Architecture Water Tour

Why not see what Chicago is most known for!?  

https://www.wendellaboats.com/Boat-Tours/Chicago-River-Architecture-Tour

Go to the Signature Room at the 95th located in the John Hancock building or the Terrace at the Trump. Enjoy a drink or meal with a nice view. Oh and don't bother going to a Cubs game, they suck.  Hope you have a good time!

I love touring here. I like Eatally on E Ohio which is. 3 floors of all things Italaian and the best latte in town. I love getting a divvy bike and cycling along the lake - when it's a bit warmer.minlike shopping along the Magnificent Mile and just over the river. The architecture boat trip is brill.mjust walking around the loop and river North is fun.mgo up the Sears building to see the view and the Trump Tower for the bar.
It's my favourite downtown to walk around when I have some down time between bookings

Room Service 2000 (RS2000) is both an advertising and verification site used my many here in the Chicago area.  Local providers can give you more details.

If there is only one thing to visit when in Chicago, my go to place is the modern wing of the art institute.  I've been to the museums in NY and the new one outside Paris, but Chicago may have the best.  And if the weather is nice eat upstairs at the Terzzo Piano.  Great view of the city, lake and park.

Lincoln Park zoo and aborateum. Any of the river  boat architectural tours at navy pier. Maggie Daly Park. The Bean. The waterwall. Must eat deep dish pizza at Lou Malnati's. These are just a few and you haven't even gone out into the neighbors. It's gonna be a cool week so dress appropriately

The Ledge are these glass boxes that hang off the side of the Sears Tower (no self respecting Chicagoan calls it Willis Tower) and you can actually order Giordanos pizza and have a private party up there.  If only you could have sex on the ledge that would be the best date ever.  Barring that, you really should do all three even if separate.  I know it's a total tourist trap thing, it would be like going to Paris without seeing the Eiffel Tower or eating at a fine french restaurant.