Chicago In A Weekend - Winter Edition

Chicago In A Weekend - Winter Edition

Emily Winshel
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.
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Where to Stay 

Chicago Marriott Downtown Magnificent Mile
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We stayed at the Chicago Marriott Magnificent Mile. We got a good deal (I think we paid about $150 a night) and it is in a really great and walkable location. The lobby isn't huge but it does have a bar/small restaurant which also offers Happy Hour. The room was large enough and comfortable for two. We also had a nice view of the city. 

Friday Night

We got in on Friday night. We didn't plan to do too much except get settled into the hotel but ended up making a spur-of-the-moment plan to go check out 5 Iron Golf, which is an indoor golf-simulator place. They serve food and drinks and it was a fun time! While they do offer walk-ins, on a weekend night you're probably best off pre-reserving your bay. I think we lucked out and were able to snag a last minute cancellation slot online.

Five Iron Golf - The Loop
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Saturday

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ABOUT THE AUTHOR
Emily Winshel
Hi there! I am a 20-something woman living in the Philadelphia area, where I am a member of the Yelp Elite team. I am a type-A planner - I'm the person on the trip who creates and manages the detailed excel sheet itinerary, carefully created from months of research. I find the best places to see and eat, and always know the best time of day to go (and whether we need reservations or not). I love sharing my tips with friends and family and am excited to share with a wider audience!
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