Traveling to Chicago in the Wintertime

Written by: Patrick Bailey

When people choose to travel in winter, they tend to travel somewhere tropical or at least warm and sunny. Either there’s enough cold air, ice and snow where they live or if there’s not, they prefer to keep it that way.

Why Chicago, Why Now?

That doesn’t mean you shouldn’t think about cooler options, such as traveling to Chicago in the winter. You won’t get a tan from laying on a sandy beach, but it can still be a memorable and magical experience. 

You could even argue that winter is the best time to travel to Chicago because: 

  • The area is less crowded during winter. 
  • Airfares and hotels are more affordable — maybe offering discounts — since it is not the peak season.
  • The snow-capped city skylines are illuminated by festive lights, and the cold is displaced in warm winter gardens. 

Prepare for Your Trip

You will need to plan and prepare for your trip. Outdoor fun requires dressing for the weather, which can be below freezing, even below 0 degrees (F). 


  • Pair of warm thermal pants and undergarments. 
  • Fleece layer to wear on top of the thermal and regular shirt. 
  • Down jacket or puffer jacket. Not only will they trap heat better than wool, but they are crushable, affordable, and easy to pack.
  • Parka-length, hooded coat, with a high down collar with a zip, 

Plan Your Itinerary

Not everywhere or everything you might want to do will be open. Some will be closed because it is winter. Some will be closed due to the COVID-19 pandemic. And some may require reservations to make sure the numbers remain COVID-appropriate. 


  • Chicago Botanic Garden. Twenty-seven gardens, including a bonsai collection, on and around nine islands, with special events. Reservations and timed entry required.
  • The Morton Arboretum. Established in 1922 as a “great outdoor museum” of trees.
  • Christkindlmarket. The European style holiday market has gone virtual this year
  • Restaurants. Dining-in may not be safe or allowed, but outside dining in an open-sided tent with good airflow and a heat source may still be possible. 
  • Parks. Among the city’s many parks are Lincoln Park and its zoo, Jackson Park and its Osaka Japanese Garden (a restoration and expansion of Japan’s pavilion for the 1893 World’s Columbian Exposition), and Skokie Northshore Sculpture Park, .
  • Winter sports. Sledding and ice-skating rinks are available at several city parks. Some less conventional activities include cross country city skiing and hiking in snowshoes. Even winter biking is practical. 


Chicago also boasts many special events throughout the winter, though how many will carry on during the pandemic is not certain. 

Among them are:



  • Alton-Audubon Eagle Ice Festival. Approximately 300 miles from Chicago, but what a biathlon: an ice sculpture competition and eagle bird-watching excursions. 
  • Chicago Sketch Comedy Festival. Stage 773 theater hosts the largest event of its kind with improv groups from around the world. 
  • Illinois Snow Sculpting Competition (Rockford). Artists from the Prairie State compete to represent the Land of Lincoln in the US Nationals Snow Sculpting Competition. It’s 85 miles from Chicago, but worth a side trip. 


  • Enchanted Railroad at The Morton Arboretum (Lisle). A tiny train travels through trees from around the world. Not confirmed for 2021 yet. 
  • Chicago Restaurant Week. Make that two weeks. Diverse cuisine and prix fixe menus from hundreds of the Windy City’s best eateries. 


  • Chicago Theatre Week. Why should restaurants get all the fun? Sample the output of Chicago’s many stages and troupes.
  • Big Muddy Film Festival (Carbondale). Explore the best of the cinema (assuming the cinemas open), both up-and-comers and accomplished masters. It’s more than 300 miles from Chicago, but dedicated cinephiles might want to consider it; the filmmakers take questions from the audience.

Due to COVID-19 pandemic, always confirm that attractions are open and events are happening before you plan your trip.

Author Bio: Patrick Bailey is a professional writer mainly in the fields of mental health, addiction, and living in recovery. He attempts to stay on top of the latest news in the addiction and the mental health world and enjoys writing about these topics to break the stigma associated with them. If you want to find more articles by Patrick, you can find them on his personal blog or in Sunshine Behavioral Health.