Chicago Winter Travel Tips

By Viator, May 2014

4.5 928 Reviews | Add your review

Despite unpredictable weather and often chilly temperatures, winter can be a great time to travel to Chicago. However, it also takes a bit of preparation to make sure your trip goes smoothly. Here are a few Chicago winter travel tips to keep in mind as you plan your next visit.

Fly into Midway

When bad weather strikes Chicago, O’Hare seems to feel the effects more than Midway. As the smaller of the two airports, Midway generally does not experience the same level of delays and cancellations when a snowstorm or other inclement weather strikes. Along the same lines, pay attention to the weather forecasts in the days leading up to your trip in case you need to make a last minute change due to the weather.

Dress appropriately

You know the saying, there is no bad weather, just inappropriate clothing? Well that definitely applies to Chicago in the winter. Bring warm, waterproof boots to navigate snowy or slushy sidewalks; a long, down or wool jacket to protect you from the wind; and a hat, scarf and gloves or mittens to keep the rest of you nice and warm. Dressing in layers is recommended as well; it may be cold outside but when the heat is cranked up inside the restaurant or museum you’re visiting, you will want to shed a layer or two.

Embrace the cold

Many of the best things about Chicago in the winter involve spending some time outdoors. Visit the Christkindlmarket in Daley Plaza, check out the Zoo Lights at the Lincoln Park Zoo, lace up your skates to go ice skating in Millennium Park or watch the river being dyed green on St. Patrick’s Day (yes, March is still winter in Chicago). You will enjoy yourself the most if you decide to simply embrace the cold rather than fight it.

If all else fails, head inside

Not a fan of the cold? No problem, just head indoors. Winter is a great time to enjoy theater in Chicago, whether it’s a Broadway production at a theater downtown or a more intimate show at the Apollo Theater in Lincoln Park or the Shakespeare Theater at Navy Pier. It is also a good time to enjoy slightly shorter lines to visit the SkyDeck at the Willis Tower. Sports fans should head to the United Center to catch the Chicago Bulls or Blackhawks in action while museum buffs can linger for hours inside the Art Institute of Chicago, the Field Museum or the Museum of Science and Industry. And at the end of a long day of sightseeing, relax with a hot drink in front of a fireplace at the Grafton in Lincoln Square, Simon’s in Andersonville or the Ten Cat Tavern in Lakeview.

Stay warm while you sightsee

For those who don’t want to hassle with public transport or brave the cold while seeing the city, hop-on, hop-off tours are a great option. They offer narration that helps you learn about the city while traveling between major attraction in a toasty warm bus. Other bus tours may be geared towards a specific interest. Learn about the history of Chicago Blues, visit the locations where several movies were made in Chicago, or immerse yourself in the seedy history of Chicago’s mobsters.

Tours & Tickets

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Chicago City Hop-on Hop-off Tour, Chicago, null

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 864 Reviews

See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $33.00
Lake Michigan Sightseeing Cruise, Chicago, Hop-on Hop-off Tours

Lake Michigan Sightseeing Cruise

4.5 star rating: Recommended 61 Reviews

Admire all of Chicago's fabulous lakefront sights and attractions on this 40-minute Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing ...  Read more

Location: Chicago, Illinois
Duration: 40 minutes (approx.)

From USD $19.60
Chicago Holiday Stroll and Food Tour, Chicago, Day Cruises

Chicago Holiday Stroll and Food Tour

5 star rating: Highly Recommended 3 Reviews

Experience the magic of the holidays, Chicago style, on a food and walking tour of the lively downtown. Your knowledgeable guide shares holiday traditions such ...  Read more

Location: Chicago, Illinois
Duration: 3 hours (approx.)

From USD $59.00

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