Chicago is a great city - regardless of the season. Yes, even in the winter, there is plenty to do...just bundle up! This guide includes a jam-packed Chicago weekend itinerary meant for the winter. With a good balance of indoor and outdoor activities and sightseeing, you're sure to have a great trip. I've sorted this guide in the order we did things - day by day - for easy use! This is not just a list of ideas, but an actual itinerary. I did the planning and research, so you don't have to! This guide is geared toward adults. In this guide, you'll find: -Hotel recommendation -Restaurants we went to (and notes on whether they take reservations or not) -Outdoor sightseeing -Guided tour recommendation -Interactive Shows (and how to get discounted tickets) -A dispensary (it's legal in Chicago!) -Cool photo opps -Tips and tricks for a smooth experience -And more! Everything listed in this guide are things I personally did during a weekend trip to Chicago - so I am speaking from experience and honest reviews. We flew in on a Friday night so that we could kick our itinerary off first thing Saturday morning, and flew out on an early Monday morning flight. There was only a one-hour time difference from our home city, so we didn't really need to adjust to the time difference.