ORD - YWG
Find cheap flights from Chicago to Winnipeg from C$ 254
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 20/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap flight deals from Chicago to Winnipeg (ORD-YWG)
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.Flights from Chicago to Winnipeg - Travel Insights & Trends
Get data-powered insights and trends into flights from Chicago to Winnipeg to help you find the cheapest flights, the best time to fly and much more.
What’s the cheapest day of the week to fly from Chicago to Winnipeg?
If your flying dates are flexible, you should consider flying to Winnipeg on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago to Winnipeg. For your return ticket, we recommend flying on a Sunday and avoiding Fridays for the best deals.
What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?
The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost C$ 521 on average. On the other hand, the most expensive months are December and August, where the average cost of tickets is C$ 1,226 and C$ 1,007 respectively.
How far in advance should I book a flight from Chicago O'Hare Intl Airport to Winnipeg?
To get a below average price on the flight from Chicago O'Hare Intl Airport to Winnipeg, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 days before departure.
Which airlines provide the cheapest flights from Chicago to Winnipeg?
The cheapest return flight ticket from Chicago to Winnipeg found by KAYAK users in the last 72 hours was for C$ 528 on WestJet, followed by Delta (C$ 642). One-way flight deals have also been found from as low as C$ 317 on Air Canada and from C$ 328 on Delta.
How many flights are there between Chicago O'Hare Intl Airport and Winnipeg per day?
There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Winnipeg, with an average flight time of 2h 26m. The most common departure time is 1:00 p.m. and most flights take off in the afternoon. Each week, there are 7 flights.
Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Winnipeg?
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
How long does a flight from Chicago to Winnipeg take?
Direct flights cover the 1,829 km separating Chicago to Winnipeg in about 2h 24m.
What’s the earliest departure time from Chicago to Winnipeg?
Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 1:03 pm and will be landing in Winnipeg at 3:29 pm.
What’s the latest departure time from Chicago to Winnipeg?
If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Winnipeg jets off at 1:03 pm and lands at 3:29 pm.
When to book flights from Chicago to Winnipeg
FAQs for booking Chicago to Winnipeg flights
Top tips for finding a cheap flight from Chicago to Winnipeg
Prefer to fly non-stop from Chicago to Winnipeg?
Find which airlines fly direct from O'Hare Intl to Winnipeg, which days they fly and book direct flights.
Nonstop departures
Chicago O'Hare Intl to Winnipeg
Monday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Tuesday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Wednesday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Thursday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Friday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Saturday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Sunday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Nonstop returns
Winnipeg to Chicago O'Hare Intl
Monday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Tuesday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Wednesday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Thursday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Friday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Saturday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Sunday
Air Canada, Air New Zealand, United Airlines
Air Canada, Air New Zealand, +1 more
Top airline flying from Chicago to Winnipeg
All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.
All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.
You do not have a space for flight cancelled. BUT!!! Air Canada handled it great. Was booked on another airline for the next day. The original flight was booked solid. But he precheck by the maintenance found a mechanical problem and the plane was not safe to fly. It was an inconvenience to have to wait until next day but I would rather arrive safely.
Very good other than we have to wait for one crew and we’re delayed and the pilot and his co- pilot has to make a difference to be right on time arrival. Disappointed about no food service also.
I had written all my complaints on my trip from Grand Junction to Denver so I will repeat it here! I was absolutely appalled that I had to pay for a regular seat that I choose 24 hrs before boarding! Also I checked my large bag which I had to pay for as well, and by the time I boarded all the room in the bins were gone so also had to check that one. I noticed people pulling out oversized suitcases, bigger than the measurements stated for carry on, and also large pack packs stuffed full! So these people were taking up 2 or 3 spaces that the rest of us should have been able to use but couldn’t! NoTV on the flight! Thankfully I had downloaded the United Airlines app and was able to watch movies on my phone. Don’t remember the last time I flew in a plane with no movie screens!
Easy boarding, roomy seats, plenty of good food, very helpful snd friendly staff. Very smooth flight! Only thing that could have been better was to have cranberry juice. Women like this as it helps avoid UTI’s and not as sweet as other juices.
The crew was friendly, the seats are too small. Air travel is barely tolerable anymore.
Food was icecold or frozen including breakfast. Hopeless service. Rude crew.
The flight was very uncomfortable and there was no snacks served for the 13 hours international flight. In addition, the flight was delayed 3 hours
Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.
Cabin crew were great. Seats are criminal for tall people
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Chicago - Winnipeg Flights
Departure:
Chicago (ORD)United States
Destination:
Winnipeg (YWG)Canada