Looking to do an anniversary trip this fall at the end of October. (4-5 days in USA only) We want to try locations new to us. Still trying to decide, but our top contenders are Boston or Chicago. Friends have suggested many other places too that we are considering. We're also trying to avoid places we've been before. We like to explore/ see things as opposed to just chilling on a beach or in a cabin. Some relaxation is cool, just not a whole trip like that. My quick question for now is about Covid vaccines and restrictions. Have all the big cities dropped their vaccine and booster requirements/ checking cards ? I've googled, but read mixed things about enforcement. Is anyone checking at all anymore? Will there be restaurants still asking? Any other thoughts related to that? Do you think they could bring it back if numbers go up?
Also, how's the weather at that time? I'm guessing a toss up. We went to the northeast in late October years ago and had gorgeous weather in the 70s, but reading weather blogs that looks like an anomaly. What should I expect truly? Both cities show the same average high/ low for our dates. What about feels like? Which is better weather wise for exploring the city on foot?

Any other info appreciated. If you'd pick one over the other, share away.

Just got back from Chicago a month ago and nobody required proof of any vaccines or even masks. Public transit still has signs up saying masks are required, but it's 50/50 most places you go.

Definitely recommend Chicago as a destination, though. Stayed inside the west loop and had a great time, tons of walking but we saw a lot. We saw the Cubs at Wrigley and did an architecture boat tour with Wendella (both must-dos). We felt safe and everyone we encountered was nice. Also do Sears Tower, Millennium Park, and try multiple pizza places (Lou Malnati's and Giordano's are so different).

Thank you for taking the time to reply. I really appreciate it. It looks like we are doing Chicago. We only have Saturday- Wednesday. Travel to Boston ended up always having a connection (using airline miles) so the flight time was much longer and with the current airline climate of cancellations/ reschedules too, we felt it too hard for this trip. We'd be traveling most of the first and last day which would leave us only 3 days really. Chicago had plenty of nonstops which left lots of time for us on arrival and departure days and less risk with flights.

Any other Chicago advice is appreciated.

Of those two cities, I have far preferred Boston, but people do love Chicago. Weather in early October or more likely to be very pleasant in both cities, I'd even say that's an ideal week. Tons to do in both cities, so they are perfectly good picks.

On the COVID front, I would be really surprised if you have any problems, even if there is another surge. But according to many, we are in a surge right now that might be bigger than Omicron, and things are fine. But what do I know… two weeks to stop the spread, right? All that being said, IF there is to be a problem with COVID, those cities are going to be amongst the first to revert, along with NY, Seattle, and LA.

I'll throw out on location that nobody ever considers: Flagstaff, Arizona.

Flagstaff is a mountain town that, if you were plopped into it and just looked around, you'd guess you were in Colorado, so not what you typically thing of for Arizona. From Flagstaff, you are within an hour or two of the Grand Canyon, Sedona, Monument Valley, Petrified National Forest, Meteor Crater park, and even Phoenix if you want something in a city. You can even do a day trip to Zion or Bryce from Flagstaff, although a little farther away.

If your wanting a city vacation, that's not the pick, but if you want adventure and lots to do, it provides a lot.

Edit: I see you made your pick. Have fun in Chicago. Weather should be perfect.