Weekend In Chicago In Winter: How To Make The Most Out Of Your Gateway

Hello there! I hope everyone had a great holiday season. My husband and I have just come back from an amazing 3 days weekend in Chicago, and I couldn’t wait to share it with you. Truth be told, the idea of going to a windy city occurred when we realized that our yearly Christmas trip to Denver, CO was not going to happen. 
We have been to Chicago 3 years ago in September, but have never experienced it during winter. We were warned about the cold and snow, but that’s what the holiday season is about for us. (Especially because we live in Austin, TX). Long story short, it took me about 15 minutes to find flights and accommodation and another 5 minutes to convince my husband that it’d be a great idea because Chicago, IL is still among the best cities for a weekend gateway in the USA. We desperately needed to get out of Texas and experience something different. 
Now, if you’re planning a relaxing weekend gateway to this amazing one of a kind city in winter, maybe our input would help you. 

Winter in Chicago is far from mild, and it is nothing like snowy Colorado. But they’re so many things to do and see, and so many places where you can treat yourself to a cup of hot chocolate or tea, that it doesn’t seem to be an issue. In the end, you’re always on the go. 

The last time we came, we went for a hotel that was farther from downtown, so we could save some $$. However, this time I wanted “home away from home” with a walking distance to most places. Airbnb seemed like a great option, and I would highly recommend finding the apartment that would be in a great neighborhood. For instance, we stayed next to Dave&Busters, just next to Lou Malnati’s Pizzeria.

The public transportation system in Chicago (CTA) is something I wish for here in Austin. You can easily avoid traffic by taking train and/or bus to a destination. It would take you about 45 minutes to get from Chicago O’Hare International Airport to Downtown by train. I would highly recommend purchasing Unlimited-ride passes from any Ventra Vending Machine. They can be used on both buses and trains and will save you a lot of money on transportation. Unlike in Europe, where your day pass would be valid until midnight of the same day. 

If you’re hoping to have a relaxing weekend in Chicago rather than a busy expedition, I would suggest spending more time wandering around beautiful neighborhoods of the city. In the end, that’s what it is famous for. We also:

  • spent a day at The Art Institute of Chicago. I consider it to be the best museum in town, so it’s worth time and money. Even if you have only a few hours to spare, this museum is a must.
  • went ice skating at the McCormick Tribune Ice Rink. Located at Millenium Park, this is a perfect place to enjoy this winter activity. We both like ice skating but it’s hard to find an outdoor ice rink of that size in Texas. You can stay for as long as you wish and the only charge is skate rentals. Also, the good news is the rink is scheduled to remain open through March 8. 
  • Recorded our version of “Smellly cat” at Friends Central Perk Pop Up at AT&T store at Michigan Ave. If you love “Friends” TV Show as much as we do, this place will bring you so much joy!
  • Spent so much time exploring Christkindlmarket Chicago. If you have never been to Christmas Markets in Germany, but would love to get a sneak peek, that’s the place to be. It is truly one of a kind experience. You can find anything from German mulled wine and pretzels to traditional toys and decorations. 
  • we did some shopping as well. Because how can you not shop when in Chicago? 😉 



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