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Know Before You Go: Visiting Chicago in Winter

By Viator, October 2017

4.5 995 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 Chicago Midway International Airport
When bad weather strikes Chicago, O'Hare International Airport 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.

Dress appropriately
You know the saying: "There's no such thing as bad weather, only inappropriate clothing." This definitely applies to Chicago in 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
Luckily for winter travelers, Chicago has a number of world-class indoor attractions. Check out the theater scene, whether it's a Broadway production downtown or a more intimate show at the Apollo Theater in Lincoln Park, or enjoy slightly shorter lines at the SkyDeck at 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 dont 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 attractions in a warm bus. Other bus tours geared toward specific interests may cover Chicago blues history, famous movie film sites, or Chicago's seedy mobster past.

Tours & Tickets

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

4.5 star rating: Recommended 908 Reviews

Explore Chicago at your own pace during this hop-on hop-off bus trolley of the city. Choose between a 1-, 2-, or 3-day pass depending on your trip time. See ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $30.99
Chicago Holiday Stroll and Food Tour, Chicago, Hop-on Hop-off Tours
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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 $53.10
$59.00 Save $5.90
Lake Michigan Sightseeing Cruise, Chicago, Walking Tours
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Lake Michigan Sightseeing Cruise

4.5 star rating: Recommended 84 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 $25.76

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