Chicago to Winnipeg Flight Tickets

Compare the best flight deals from Chicago to Winnipeg

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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

Popular Chicago - Winnipeg Flights

Airlines on Chicago - Winnipeg Route

Chicago Airports

Winnipeg Airports

Alternative Routes

Chicago - Winnipeg Flight Summary

AIRLINES
United Airlines

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.

Winnipeg J.A. Richardson International Airport (YWG)

From Airport to City Center

Uber: You can reach the city center from the airport terminal via the Uber app. The journey takes approximately 15-20 minutes depending on traffic. Uber service operates 24/7, with drivers waiting at designated pickup points.


Taxi: Official taxi stands are located at the terminal exits and provide direct access to the city center. The journey time again varies between 15-20 minutes depending on traffic. Taxi service is offered 24/7 without interruption.


Rental Car: There are offices of several rental car companies within the terminal. Driving to the city center takes about 15-20 minutes. Car returns can be made at any time of the day, but some companies may offer limited service during night hours.


Bus: There is no direct bus line between the airport and the city center, but transfer via Winnipeg Transit is possible. Bus services are limited and may require additional transfers.


Bicycle: There is a bicycle path infrastructure around the airport. Cycling to the city center may take about 30-40 minutes, but weather conditions should be considered.

Frequently Asked Questions About Chicago - Winnipeg Flights

Chicago to Winnipeg flight ticket prices vary depending on the season, airline, and how far in advance you book. Use the search form above to see the latest prices.
For Chicago, you can use Meigs Airport (CGX), Chicago Rockford International Airport (RFD), Chicago Executive Airport (PWK), Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), DuPage Airport (DPA). For Winnipeg, you can use Winnipeg J.A. Richardson International Airport (YWG).
The flight duration from Chicago to Winnipeg varies for direct flights. Connecting flights may take longer depending on the number of layovers.
United Airlines operate direct flights from Chicago to Winnipeg.
Generally, off-season periods and weekdays offer more affordable tickets. Booking early can also help you save on prices.
Various airlines operate on this route. Search to see the latest prices.