Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Winnipeg to Chicago is WestJet.
Cheapest Month
August
Travel Period: March 2025 - February 2026
The cheapest month(s) to fly from Winnipeg to Chicago is August.
Cheapest Day of the Week
Monday
The cheapest day(s) of the week to fly from Winnipeg to Chicago is Monday.
How far is Chicago from Winnipeg?
The flight distance between Winnipeg and Chicago is 1154km. Check all available flights on Wego.
Popular Destinations From Chicago
Popular Destinations From Winnipeg
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel Central Loop
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel
