Where to Stay

Ambassador Chicago

This Gold Coast gem is absolutely stunning this time of year. From the gorgeous Christmas decorations to the historic memories of the hotel and the fun musical performances in the bar area, this is a must for anyone visiting or living in Chicago. If you’re visiting, this is a great option and if you’re local, check out the bar for a little date night.

Where to Eat

• Deuces and the Diamond

This fun little spot in Wrigleyville is known for being a great place to go at 1 a.m. *cough, cough. That doesn’t mean it should be looked over. It has incredible decorations and is a perfect spot for Christmas content for the ‘gram.

• The Walnut Room

This is a classic in Chicago. Located in the middle of the historic Macy’s, the Walnut Room is adorned with a jaw-dropping tree and is perfect for a Christmas-themed brunch.

• There are so many Christmas themed restaurants this year. Eater did a great summary of them here.

Where to Shop

Macy’s

Probably an obvious but the Macy’s in Chicago is a great holiday shopping destination. The exterior mirrors the Fifth Ave. window displays in New York City and the golden trumpets are a sight to see. The store has gorgeous decorations, a fun Christmas market section on its lowest level and is a great place to snag Chicago-themed Christmas gifts.

What to Do

• Christkindlmarket

Again, another obvious, but the Christkindlmarket in Chicago is one of my favorite holiday traditions. Sample delicious hot chocolate and treats, explore unique crafts and holiday decor and enjoy the spirit of Christmas. It gets insanely crowded during the weekends, so I recommend trying for a Monday-Thursday visit.

• Ice Skating Rink at Millennium Park

I’m not a fan of ice skating but I’m glad I can say I skated under the bean one year. It’s a great experience and just a beautiful sight. While waiting in line last year we say four proposals so if you like romance, it’s a great place to people watch.

• Zoolights

The Lincoln Park Zoolights are so much fun! Grab hot chocolate or wine (21+ years old please!), walk around the zoo and see the colorful lights. Often in fun shapes, the lights are magical. You can often see some of your favorite animals too!

Honestly there is so much to do in Chicago at Christmas time, it’s pretty overwhelming. This list is pretty classic, but I’m a fan of classic during the holidays. These are my favorites, and pretty much must-dos, since moving here.

Have you been to Chicago in Christmas time? What’s your favorite winter activity?