Chicago to Winnipeg Flight Tickets
Compare the best flight deals from Chicago to Winnipeg
About Chicago - Winnipeg Flights
Find the best prices for flights between Chicago (United States) and Winnipeg (Canada) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Chicago has 6 airports, while Winnipeg has 1 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Chicago - Winnipeg Flights
Best month to fly
June 2026 - 7,024 ₺
June 2026
7,024 ₺
1 stops
CheapestApril 2026
21,066 ₺
1 stops
| Ay | Flight Type | Price |
|---|---|---|
| June 2026Cheapest | 1 stops | 7,024 ₺ |
| April 2026 | 1 stops | 21,066 ₺ |
Prices may change. Based on recent searches.
Popular Chicago - Winnipeg Flights
Chicago - Winnipeg
Winnipeg - Chicago
Airlines on Chicago - Winnipeg Route
Chicago Airports
Winnipeg Airports
Alternative Routes
Alternative Routes from Chicago
Chicago - Winnipeg Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
Chicago and Winnipeg - Airport Transportation
O'Hare International Airport (ORD)
How to Get to the Airport
Metro/Train: You can reach the airport in 40-45 minutes by taking the CTA Blue Line train from downtown Chicago. Services run every 5-15 minutes and operate 24 hours a day.
Bus: You can reach the airport by taking buses departing from downtown bus stops (e.g., around Union Station). The journey takes approximately 45-60 minutes, with buses departing every 15-30 minutes.
Taxi: Transportation from downtown Chicago to O'Hare by taxi is possible. The journey takes 30-60 minutes depending on traffic, and taxis operate 24 hours a day.
Airport App-Based Rides (Uber/Lyft): You can reach O'Hare from downtown via Uber or Lyft. You can request a ride through the app and board at designated pickup points.
Car Rental: You can reach the airport by renting a car from rental offices located in the city center. Information on rental procedures can be obtained from rental offices at the airport.