Winnipeg to Chicago Flight Tickets
Compare the best flight deals from Winnipeg to Chicago
About Winnipeg - Chicago Flights
Find the best prices for flights between Winnipeg (Canada) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Winnipeg has 1 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Winnipeg - Chicago Flights
Best month to fly
June 2026 - 6,798 ₺
June 2026
6,798 ₺
1 stops
CheapestApril 2026
12,931 ₺
2 stops
| Ay | Flight Type | Price |
|---|---|---|
| June 2026Cheapest | 1 stops | 6,798 ₺ |
| April 2026 | 2 stops | 12,931 ₺ |
Prices may change. Based on recent searches.
Popular Winnipeg - Chicago Flights
Winnipeg - Chicago
Chicago - Winnipeg
Airlines on Winnipeg - Chicago Route
Winnipeg Airports
Chicago Airports
Alternative Routes
Alternative Routes from Winnipeg
Winnipeg - Chicago Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
Winnipeg and Chicago - Airport Transportation
Winnipeg J.A. Richardson International Airport (YWG)
How to Get to the Airport
Uber: You can easily reach the airport from the city center using the Uber app. The journey takes approximately 15-20 minutes. Uber service is active 24/7, and you can plan your trip by making a reservation in advance.
Taxi: Transportation to the airport is possible from taxi stands in the city center. The journey time is 15-20 minutes depending on traffic. Taxi service is available at any time of the day.
Rental Car: You can return rental cars hired in the city center at the airport. The drive takes about 15-20 minutes on average. Most rental car companies operate 24/7.
Bus: Although there is no direct bus line from the city center to the airport, transportation is possible via Winnipeg Transit's transfer routes. Bus services are limited and may require additional transfers.
Bicycle: It is possible to reach the airport by bicycle from the city center. The journey takes approximately 30-40 minutes, and weather conditions should be taken into account.
O'Hare International Airport (ORD)
From Airport to City Center
Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.
Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.
Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.
Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.
Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.