Chicago in Feb

While per city guidelines you are supposed to quarantine upon arrival OR receive a negative test 72 hours prior, there's not really much enforcement of it. It's not really possible.

One thing to watch out for is if you're booking a hotel, some of them may require it, depending on where you're coming from. I think it's been hit and miss.

Otherwise, the city is actually slowly starting to open back up. As of Saturday, indoor dining resumed and theaters/museums were allowed to reopen.

Other than it being cold as hell, assuming you follow the normal covid guidelines of wearing a mask, etc., then I doubt you'll have any issues.

Though indoor dining reopened, as mentioned, at very limited capacity, there are more places than I anticipated that are choosing to remain closed for to-go or outdoor only. Outdoor is relative for some places... you’ll see true outdoor patios with heaters or enclosed tents that really pushed the city’s restriction.

In general, it’s not the worst time to visit Chicago with the lifted restrictions, but it’s cold and you’ll need a reservation for the weekend. I went to Recess on Friday night and stayed for one beer. It was one degree with the windchill and the fire pit didn’t do much.

ETA: To answer your question, my buddy had a pretty small wedding earlier in the month. Most everyone from out of town stayed at theWit down in the Loop. No one quarantined, if that tells you anything.