Snowing in Chicago

Chicago is a wonderful city with endless opportunities for entertainment and recreation. Chicago’s world-class cultural attractions and amazing architecture are the standouts of this great city. Unfortunately, many tourists never consider Chicago to be a winter vacation destination due to the frequent snow storms and frigid temperatures. Luckily, many of the best attractions are located indoors, and the festive outdoor attractions are worth braving the cold, bundled up of course!

Do you think of Chicago as a summer only destination? You are missing out big time if a winter vacation has never crossed your mind! In Chicago, there is plenty of fun to be had year-round! As a long time former resident, I have come up with some of my favorite things to do over the winter months. In fact, I actually prefer the winter months due to the quieter atmosphere and abundance of tranquil dreary, snowy days. Fewer crowds, discounted hotels and attractions, and a laid-back appeal are just some benefits of visiting over the winter season.

Whether you are a local looking for new interesting activities this winter, or a tourist planning a winter getaway, you are bound to find a few ideas for winter fun on my list. What are your favorite Chicago winter activities? Feel free to give your own suggestions in the comments below!

1. Visit The Art Institute

Art Institute of Chicago at Christmas

The Art Institute of Chicago is one of the world’s best art museums. Visiting at any time of the year is a once in a life experience, however, visiting during the holiday season is even more spectacular! The beautiful lions out front wear festive wreaths during the holiday season! On a budget? Visit Thursday nights for free admission (5-8pm for Illinois residents). Special holiday displays (Neapolitan Crèche), festive decor, and choir performances add an extra festive touch during the season.

Address: 111 S. Michigan Ave. Chicago, IL 60603

2. Ice skate in Millennium Park

Millennium Park Ice rink

Ice skating at the McCormick Tribune Rink at Millennium Park is one of my favorite winter past times in the city. There is nothing better then heading downtown on a brisk, snowy winter day, and taking in the spectacular Chicago architecture while skating along to holiday music. Great prices for a city rink! One of the few city ice rinks you will find offering free admission (your only cost will be skate rentals, unless you own a pair). Bonus – free skating lessons are offered weekend mornings. Snacks, coffee, and hot cocoa available for purchase.

Address: 55 N. Michigan Ave. Chicago, IL 60601

3. Take a stroll down Michigan Avenue

Magnificent Mile in Chicago

Michigan Avenue: home to the world famous Magnificent Mile shopping district. How could you not want to spend your holiday season shopping along this beautiful street, complete with prestigious shops, amazing restaurants, and scenic holiday decor?! Definitely plan for a stop at Water Tower Place, an upscale 8 floor shopping center located at 835 N. Michigan Ave.

In addition, be sure to check out the Magnificent Mile Holiday Lights Festival, which takes place every November. This popular, festive event include many activities: a parade, concerts, and a fireworks show over the Chicago River.

Address: N. Michigan Ave. Chicago, IL 60610

4. Experience an authentic Italian dinner at The Rosebud

The Rosebud - Chicago

A winter visit to Chicago would not be complete without a delicious Italian dinner at my favorite restaurant, The Rosebud. This upscale restaurant located in Chicago’s Little Italy neighborhood features a spectacular menu, a romantic setting, and impeccable service. Try the Cheese Ravioli or Chicken Parmesan. On an interesting side note, this charming restaurant was Frank Sinatra’s favorite: imagine that!

Address: 1500 W. Taylor St. Chicago, IL 60607

5. Be amazed at Lincoln Park ZooLights Festival

Lincoln Park Zoo Lights Chicago

Take advantage of this festive display of over 2 million lights, held annually each year at Chicago’s beautiful Lincoln Park Zoo. This free event features multiple themed holiday activities including ice carving demonstrations, carolers, and a synchronized music and light show. The ice carvings are absolutely fantastic; these artists really have a unique talent. Strolling around Zoo Lights is the perfect holiday and date night activity: strolling around with a hot chocolate in hand while taking in the wonder of all the dazzling lights is really one of the best things to do in the city in December.

Update: Admission is now $5. Mondays are free.

Address: 2001 N. Clark St. Chicago, IL 60614.

6. Visit the spectacular dinosaur & mummy exhibits at The Field Museum

The Field Museum Chicago

Most of you have probably heard about Chicago’s famous Field Museum. Reading about this museum is much different than actually seeing the incredible dinosaur fossils in person. Home to “Sue,” the most complete fossil, The Field Museum is tops on my list of must-dos in the city. Take a break from shopping in the cold, brisk Chicago air to tour this incredible museum! If you plan on visiting The Field & the Shedd, along with other Chicago museums and attractions, you should definitely look into a combined attraction discount from CityPass.

Address: 1400 S. Lakeshore Drive Chicago, IL 60605