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 ... 

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Tours & Tickets

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 523 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 $35.00

Lake Michigan Sightseeing Cruise

4 star rating: Recommended 3 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 $18.53

Chicago Holiday Stroll and Food Tour

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 $54.45

Chicago Pizza and Christmas Sights Walking Tour

Combine holiday sights with real Chicago pizza on a 3-hour Christmas walking tour around the city! While admiring the city’s traditional Christmastime ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $47.00

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