2 days in Chicago then driving to Florida - any tips?
Taking 3 weeks this winter for a leisurely round trip. Leaving Tampa in time for Christmas in Denver. Heading up to Rapid City to see the big heads, then shooting over to Chicago in time for New Year’s.
I’m sure Chicago isn’t lacking stuff to do to bring in the New Year, and we are there from 29th-1st. Good areas to stay? Hidden gem things to do/see? We are prepared to be cold as shit, so not opposed to outdoor activities.
Trip from Chicago back to Tampa - we have no idea what’s along the way. We like quirky markets/antiques, historic districts, pretty stuff in nature, etc.
We are taking a few days to get back, so if there’s a place worth staying on the way (we were thinking Chattanooga?) we have a good amount of spare time.
Thanks in advance!

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