Chicago North America

Chicago Winter Bucket List 2.0

Last year, I created a short Winter Bucket List (read more here) on the blog and to my surprise, it’s now become my most read, saved, and shared post OF ALL TIME. I found myself creating a short list on my phone of upcoming activities and thought, why not share with all of you! 

With the craziness of the holidays approaching (and one too many trips planned), it’s nice to have a few nights laid out with my husband and our friends. To be honest, winter is my favorite time of year in Chicago. Reservations are easy to snag, lines are short, and one of my favorite festivals comes to town (see #1).

Without further adieu, here’s what I am looking forward to this winter:

Drink Mulled Wine at the Christkindlmarket. 

This is hands down one of my favorite things to do in Chicago. It’s a large, German Christmas festival that sets up in the Loop . There is endless mulled wine, authentic German food, ornament stores, and hundreds of vendor booths. A great place to snag unique presents!

Grab a Friend and Head to the Mag Mile Lights Festival

The weekend before Thanksgiving, the big celebration kicks off. Grab a friend and head to Michigan Avenue to secure a spot along the parade route and watch as they light up the holiday trees during the nation’s largest evening holiday celebration.

Get in Line at SNL: The Exhibit

I am heading to this exhibit next week and could not be more excited! As a huge SNL fan, the sets designs look insane and it will be so fascinating to dive into the history of such an iconic show. I’ll be sure to share more after I explore the exhibit!

Rent an Igloo at City Winery

This genius idea was created for us Chicagoans that want to be outside, no matter the weather. You can rent one of these domes for up to 6 people for 90 minutes (which includes wine and a charcuterie board). I think this would be a fun way to celebrate a birthday or anniversary!

Hit Up One of the City’s Newest Bars

My never-ending list of restaurants and bars seems to be getting longer and longer. In fact, I am hardly making a dent. Some of my favorite spots this winter will include: The new Boka restaurant next to the Viceroy hotel, Somerset; Chicago’s first self-pouring bar, Tapster; and the hidden gem, Blind Barber, found in the back of a barber shop.

Spend the Evening at a Broadway Show. 

An evening at the theater always sounds like a romantic evening to me. This year, Broadway in Chicago is showcasing some incredible shows. From Les Miserable to Wicked to The Color Purple, there is definitely a show for you.

Take a Spin on the Rink.

Chicago has numerous ice skating rinks throughout the city, and almost all of them seem to have an amazing view. My personal favorite is the new Maggie Daley Ice Skating Ribbon. You’ll find skaters of all ages and the incredible Chicago skyline as your backdrop. After skating, grab a Hot Chocolate to go and head over to take a quick picture at the Bean.

Take a Stroll through the Garfield Park Conservatory.

When the winter blues start to hit, you can find yourself some signs of summer at the Garfield Park Conservatory. Open all year round, this conservatory is free to the public and features multiple “rooms” such as the Palm House or Desert House.

Snag a Reservation for Chicago Restaurant Week.

If you’re a foodie like me, Chicago Restaurant Week is a dream come true. Back for it’s 11th year, hundreds of restaurants offer prix fixe menus for lunch and dinner during this week in January.

What is at the top of your Winter Bucket List?

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