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ORD - YWG

Find cheap flights from Chicago to Winnipeg from C$ 250

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 19/6. 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.
1 adult
0 bags
Sat 25/5
Sat 1/6

Search 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
In the last 7 days, travellers have searched 44,979,812 times on KAYAK, and here is why:

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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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:40 p.m. - 3:25 p.m.ORD-YWG
20h 45m2 stops
6:30 a.m. - 9:06 p.m.YWG-ORD
14h 36m2 stops
C$ 512
Find Deal
Tue, 28 May - Wed, 3 Jul
10:57 p.m. - 7:03 p.m.ORD-YWG
20h 06m3 stops
6:30 a.m. - 9:06 p.m.YWG-ORD
14h 36m2 stops
C$ 516
Find Deal
Tue, 28 May - Wed, 3 Jul
3:55 p.m. - 11:29 p.m.ORD-YWG
7h 34m1 stop
6:55 a.m. - 2:59 p.m.YWG-ORD
8h 04m1 stop
C$ 545Delta
Find Deal
Tue, 11 Jun - Thu, 13 Jun
8:30 a.m. - 7:48 p.m.ORD-YWG
11h 18m2 stops
8:00 a.m. - 4:31 p.m.YWG-ORD
8h 31m1 stop
C$ 554
Find Deal
Sun, 26 May - Fri, 5 Jul
7:00 a.m. - 3:25 p.m.ORD-YWG
8h 25m1 stop
8:00 a.m. - 6:34 p.m.YWG-ORD
10h 34m1 stop
C$ 558
Find Deal
Wed, 29 May - Thu, 4 Jul
3:55 p.m. - 11:29 p.m.ORD-YWG
7h 34m1 stop
6:55 a.m. - 4:48 p.m.YWG-ORD
9h 53m2 stops
C$ 568Delta
Find Deal
Tue, 11 Jun - Thu, 13 Jun
6:07 a.m. - 10:40 p.m.ORD-YWG
16h 33m2 stops
8:50 p.m. - 5:05 p.m.YWG-ORD
20h 15m1 stop
C$ 571WestJet
Find Deal
Tue, 4 Jun - Sat, 8 Jun
9:15 p.m. - 9:47 a.m.ORD-YWG
12h 32m1 stop
7:30 a.m. - 2:54 p.m.YWG-ORD
7h 24m1 stop
C$ 608Air Canada
Find Deal
Fri, 21 Jun - Tue, 25 Jun
5:40 a.m. - 3:25 p.m.ORD-YWG
9h 45m1 stop
8:00 a.m. - 11:59 p.m.YWG-ORD
15h 59m1 stop
C$ 621WestJet
Find Deal
Wed, 29 May - Mon, 8 Jul
9:15 p.m. - 9:47 a.m.ORD-YWG
12h 32m1 stop
4:18 p.m. - 11:59 p.m.YWG-ORD
7h 41m1 stop
C$ 645Air Canada
Find Deal
Tue, 18 Jun - Wed, 19 Jun

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?

The average price of all 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 Wednesday, 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 Saturdays 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 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$ 522 on average. On the other hand, the most expensive months are December and August, where the average cost of tickets is C$ 1,228 and C$ 1,009 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Winnipeg?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Winnipeg, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
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 price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago to Winnipeg found by KAYAK users in the last 72 hours was for C$ 545 on Delta, followed by WestJet (C$ 571). One-way flight deals have also been found from as low as C$ 275 on WestJet and from C$ 300 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?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
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 26m.

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.

Good to know

Low season

January

High season

July

Cheapest flight

C$ 250
Best time to beat the crowds (20% less expensive on average)
Most popular time to fly and prices are also 11% lower 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$ 183 for a one-way ticket and C$ 374 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.

See more FAQs

Top tips for finding a cheap flight from Chicago to Winnipeg

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 276 or less one-way.

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

See more nonstop flights

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

See more nonstop flights
See more nonstop flights

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.
7.0
Air CanadaOverall score based on 6862 reviews
6.2food
7.0comfort
7.8crew
7.2boarding
6.8entertainment
Airline reviews

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

2.0 MediocreAnonymous, Apr. 2024LGA - YYZ
Read more about Air Canada reviews

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

Flight was delayed 1.5 hrs due to problem with a previous flight to mine; I was informed appropriately via Text & Email, however, website did not keep up with messages sent by nearly an hour. When checking-in warm & friendly reception at check-in desk until female Air Canada Rep noticed my flight number and instantly pivoted to a condescending & sarcastic comments about getting my bag checked in since I’m running so late; then tone instantly changed again few minutes later when she muttered, “Oh, they’ve delayed it” another sign systems & worse front line staff, not fully informed or simply not reading their flight status updates. Flight crew were very friendly & did a great job trying to make up lost time due to the delay.

It was great, love the experience and will definitely recommend 👌. Communication was great

My flight was great! Gate attendants and crew were great… pleasant and in good spirits. Flight delayed several hours and we were well informed of the status while on plane. Thank you!

The fact that I got to Toronto alive and well and safe is a huge plus. I thank the captain and crew for a safe flight The comfort of the aircraft leaves much to be desired. Human beings should not have to be that cramped and squashed on a flight that we pay a lot for and even have to pay for lousy food choices The cabin crew were pleasant and helpful Kudos to them as the flight was packed to capacity and there was a lot of work for them in a short space of time All in all a good experience, but too cramped

It was great to check carryon luggage at no charge when there was no room for ours. A hidden benefit of having low-tier tickets. Also great to stay off plane as long as possible. Airline gave us seats we wanted on this last leg, again at no charge.

The late departure Of two hours waitresses, immature, and gossiping

We had a good flight, service was good and lots of leg room. Service was good and the staff were friendly.

Book cheap flights from Chicago to Winnipeg

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Winnipeg found on KAYAK in the last 72 hours.
19/6Wed
1 stop
18h 04mORD-YWG
C$ 250
21/7Sun
3 stops
15h 12mORD-YWG
C$ 267
26/5Sun
1 stopWestJet
8h 25mORD-YWG
C$ 275
23/7Tue
1 stopDelta
7h 28mORD-YWG
C$ 300
23/7Tue
2 stopsDelta
10h 00mORD-YWG
C$ 307
22/7Mon
2 stopsWestJet
9h 25mORD-YWG
C$ 363
26/5Sun
directAir Canada
2h 26mORD-YWG
C$ 419
19/6Wed
directAir Canada
2h 26mORD-YWG
C$ 565
21/7Sun
directUnited Airlines
2h 26mORD-YWG
C$ 747
26/5Sun
directUnited Airlines
2h 26mORD-YWG
C$ 860

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Last minute flights from Chicago to Winnipeg

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Winnipeg that are departing in the next 10 days.
29/4Mon
multi-stopWestJet
9h 53mORD-YWG
1/5Wed
multi-stopWestJet
14h 58mYWG-ORD
C$ 613
28/4Sun
multi-stop
17h 05mORD-YWG
3/5Fri
multi-stop
9h 27mYWG-ORD
C$ 617
30/4Tue
multi-stop
18h 31mORD-YWG
1/5Wed
multi-stop
24h 03mYWG-ORD
C$ 624
28/4Sun
multi-stopWestJet
17h 05mORD-YWG
1/5Wed
multi-stopWestJet
14h 58mYWG-ORD
C$ 642
29/4Mon
multi-stopWestJet
9h 53mORD-YWG
30/4Tue
multi-stopWestJet
9h 28mYWG-ORD
C$ 645
29/4Mon
multi-stopWestJet
8h 10mORD-YWG
1/5Wed
multi-stopWestJet
16h 22mYWG-ORD
C$ 649
28/4Sun
multi-stopDelta
5h 19mORD-YWG
30/4Tue
multi-stopDelta
11h 22mYWG-ORD
C$ 784
30/4Tue
multi-stopDelta
11h 40mORD-YWG
2/5Thu
multi-stopDelta
11h 05mYWG-ORD
C$ 862
30/4Tue
multi-stopAir Canada
12h 20mORD-YWG
4/5Sat
multi-stopAir Canada
7h 50mYWG-ORD
C$ 1,007
30/4Tue
multi-stopAir Canada
12h 20mORD-YWG
2/5Thu
multi-stopAir Canada
7h 50mYWG-ORD
C$ 1,009

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Chicago - Winnipeg Flights

Departure:

Chicago (ORD)United States

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago

Cabin classes:

C$ 728

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