ORD - YWG

C$ 123 Find Cheap Flights from Chicago to Winnipeg

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 11/10. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
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Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Winnipeg

Sat, 27 Sep - Tue, 30 Sep
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 255WestJet
Find Deal
Sat, 27 Sep - Sat, 4 Oct
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
WestJet Logo
6:15 p.m. - 4:43 p.m.YWG-ORD
22h 28m2 stops
C$ 301WestJet
Find Deal
Sat, 27 Sep - Mon, 29 Sep
Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
Logo
9:00 a.m. - 5:26 p.m.YWG-ORD
8h 26m1 stop
C$ 302
Find Deal
Mon, 22 Sep - Tue, 30 Sep
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 311WestJet
Find Deal
Fri, 26 Sep - Tue, 30 Sep
WestJet Logo
5:30 p.m. - 11:41 a.m.ORD-YWG
18h 11m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 323WestJet
Find Deal
Sat, 27 Sep - Sat, 4 Oct
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
WestJet Logo
6:30 p.m. - 4:43 p.m.YWG-ORD
22h 13m1 stop
C$ 329WestJet
Find Deal
Fri, 26 Sep - Tue, 30 Sep
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 330WestJet
Find Deal
Thu, 25 Sep - Tue, 30 Sep
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 332WestJet
Find Deal
Sat, 27 Sep - Sun, 28 Sep
Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
Logo
9:05 p.m. - 10:31 a.m.YWG-ORD
13h 26m2 stops
C$ 334
Find Deal
Mon, 22 Sep - Fri, 3 Oct
Logo
6:00 a.m. - 9:30 p.m.ORD-YWG
15h 30m2 stops
Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 336
Find Deal
Expert advice

Expert advice for your flight from Chicago to Winnipeg

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Economy Plus offers up to 15 cm more legroom than standard economy seats.


United's Priority Boarding places you in Zone 2, avoiding overhead bin space issues.

Read more about United Airlinesby Stefanie Waldek
Air Canada

Air Canada's Preferred Economy seats offer up to 10 extra cm of legroom.


Air Canada offers priority check-in for higher fare classes and elite status travelers.

Read more about Air Canadaby Stefanie Waldek
Airports
ORD

For a quick security check, avoid peak times at ORD as lines can exceed 30 minutes. Off-peak hours are much faster.

Read more about ORDby Stefanie Waldek
YWG

Use the ArriveCAN app to fill out your customs declaration in advance at YWG, saving time at the electronic kiosk.

Read more about YWGby Mark Stachiew
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Air Canada and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Mark Stachiew

Mark Stachiew

Expert on YWG

Mark Stachiew

Mark Stachiew

Mark Stachiew has been exploring the world and writing about it for more than 30 years. His travel stories have appeared in numerous newspapers, magazines and online publications in Canada, the United States and beyond.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to Winnipeg flights

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?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Winnipeg clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Winnipeg on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Chicago to Winnipeg. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Winnipeg, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost C$ 319 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is C$ 974 and C$ 900 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Winnipeg?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 417 on average.

Find deals

Good to know

Low seasonSeptember
Cheapest flightC$ 123
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly (31% more expensive on average)
Flight from Chicago to Winnipeg

When to book flights from Chicago to Winnipeg

Are your dates flexible? Find out the best times to travel from Chicago to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Winnipeg flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Winnipeg?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was C$ 89 for a one-way ticket and C$ 184 for a round-trip.

  • Which airports will I be using when flying from Chicago to Winnipeg?

    Chicago airport is called Chicago O'Hare Intl and the only airport in Winnipeg is Winnipeg.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

  • Which aircraft models fly most regularly from Chicago to Winnipeg?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.

  • Which airline alliances offer flights from Chicago to Winnipeg?

    Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.

  • On which days can I fly direct from Chicago to Winnipeg?

    There are direct flights from Chicago to Winnipeg on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Chicago to Winnipeg?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Winnipeg.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Winnipeg Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Winnipeg

Monday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Tuesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Wednesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Thursday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Friday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Saturday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Sunday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

See more nonstop flights

Direct returns

Winnipeg to Chicago O'Hare Intl

Monday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Tuesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Wednesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Thursday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Friday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Saturday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Sunday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

See more nonstop flights

Reviews of the top airline flying from Chicago to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Winnipeg. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 10000 reviews
6.3Food
6.8Entertainment
7.1Comfort
7.3Boarding
7.8Crew
Airline reviews

Very bad, flight was cancelled due to strike and staff was unable to rebook us

2.0 MediocreAnonymous, Aug 2025ORD - YUL
Read more Air Canada reviews

Very bad, flight was cancelled due to strike and staff was unable to rebook us

Because of a change in aircraft, I was unable to experience the business class I paid for and was disappointed.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

Very clean plane, staff were courteous, complimentary wifi and beverages are nice, and it was nice to have a whole row to myself! I do miss having seatback entertainment, though. And the prices are getting ridiculous, especially with the different teared tickets. But the flight overall was great.

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

Nuts would be better than pretzels as the non sweet snack

It was a short flight, and no entertainment. That was not a problem for us, but there is no option for "not applicable". There was a bit of turbulence, so there was no food service.

Everything you need to know for your flight from Chicago to Winnipeg

Information on your arrival and departure airports

Chicago (ORD)
Winnipeg (YWG)

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