My hubby and I love to take a weekend or over night trip to Chicago to celebrate our spring anniversary. We haven't been since Covid, but here are the two hotels we stayed in and loved:
Renaissance Chicago Downtown Hotel, 1 W Wacker Dr, Chicago, IL 60601
(which is not the same one that Sara listed, but pretty close. This one was right on the river so it was close to all the State street shopping and stuff and just a couple blocks from the Michigan Ave shopping. That was my favorite of the two, so these were both great locations
Hyatt Regency Chicago, 151 E Wacker Dr, Chicago, IL 60601
This one is also on the river, but further away from State street shopping. I love the stuff on State street better than Michigan ave personally because there is a Blick art store which is my FAVE and then more normal shopping places that I can afford. Ha ha!
One of the things I highly recommend is going to the restaurant on the top of the John Hancock building. We went for a glass of wine and dessert and it was a little pricey, but the view was amazing and totally worth the experience. We just walked up to the door and there wasn't a wait (in March or April) and we got a table right next to the window. You'd probably have to look up what the rules are now with covid stuff.