For something a little different, we highly recommend the Chicago crime tour. We actually did it one year as a Christmas gift to each other and had the best time—think mob stories, speakeasies, and plenty of fascinating history. It’s a fun way to see the city and switch things up from the usual sightseeing.
Chicago's legendary comedy club helped launch SNL legends like Tina Fey, Amy Pohler and Chris Farley. Catch a sketch or improv show in Old Town. It's a short cab ride from the hotel and a fun way to warm up on a February night. Make sure to grab a drink at Corcoran's or Old Town Ale House before the show!
See the city from above, just a block away from the hotel! Skydeck at Willis Tower: Step out onto The Ledge, 103 floors up, for views across the city and Lake Michigan.