Winter is really pretty in Chicago- sure it’s a little cold, but if you bundle up, have proper hats, scarves, gloves, and boots you’ll be fine!
Go to State Street and look at all the lights and window decorations- especially at Macy’s. Inside Macy’s they’ve also got it all decorated up. The Walnut Room restaurant has a giant Christmas tree.
Michigan Avenue also has tons of lights– it’s really really pretty!
Grab a sled or a piece of cardboard and find a nice hill- this one is in Lincoln Park near Wrightwood Ave.
Go for a run, LOL. It’s brisk!
Find a Christmas Tree seller and take a deep breath.
Or just walk around any of the many great Chicago neighborhoods, get a hot chocolate or a meal.