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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 191

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago O'Hare Intl Airport departing on 8/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Winnipeg to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Winnipeg to Chicago.

Cheap last-minute flights

Planning a quick getaway from Winnipeg to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Winnipeg to Chicago

Find recent round-trip train or bus tickets from Winnipeg to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:30 a.m. - 12:05 p.m.YWG-ORD
28h 35m2 stops
6:33 p.m. - 3:10 p.m.ORD-YWG
20h 37m2 stops
C$ 470
Find Deal
Tue, 10 Dec - Thu, 12 Dec
5:00 p.m. - 4:35 a.m.YWG-ORD
11h 35m2 stops
5:15 a.m. - 3:10 p.m.ORD-YWG
9h 55m1 stop
C$ 471
Find Deal
Fri, 22 Nov - Tue, 26 Nov
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 561United Airlines
Find Deal
Mon, 3 Feb - Tue, 4 Feb
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
7:10 a.m. - 1:27 p.m.ORD-YWG
6h 17m1 stop
C$ 575United Airlines
Find Deal
Tue, 10 Dec - Thu, 12 Dec
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
7:20 a.m. - 4:24 p.m.ORD-YWG
9h 04m1 stop
C$ 576Air Canada
Find Deal
Mon, 3 Feb - Sun, 9 Feb
6:45 a.m. - 1:06 p.m.YWG-ORD
6h 21m1 stop
9:03 a.m. - 4:24 p.m.ORD-YWG
7h 21m1 stop
C$ 579Air Canada
Find Deal
Sat, 22 Mar - Tue, 1 Apr
6:55 a.m. - 11:40 a.m.YWG-ORD
4h 45m1 stop
1:45 p.m. - 11:34 p.m.ORD-YWG
9h 49m2 stops
C$ 618Delta
Find Deal
Tue, 26 Nov - Sat, 7 Dec
6:40 a.m. - 4:51 p.m.YWG-ORD
10h 11m1 stop
6:00 a.m. - 11:57 p.m.ORD-YWG
17h 57m2 stops
C$ 657WestJet
Find Deal
Wed, 9 Apr - Sat, 24 May
5:00 a.m. - 4:33 p.m.YWG-ORD
11h 33m2 stops
4:45 p.m. - 12:44 a.m.ORD-YWG
7h 59m1 stop
C$ 667WestJet
Find Deal
Sat, 22 Mar - Mon, 31 Mar
6:55 a.m. - 3:54 p.m.YWG-ORD
8h 59m2 stops
8:25 a.m. - 4:55 p.m.ORD-YWG
8h 30m2 stops
C$ 796Delta
Find Deal
Thu, 28 Nov - Thu, 5 Dec
7:30 a.m. - 11:51 p.m.YWG-ORD
16h 21m1 stop
C$ 191
Find Deal
Sun, 8 Dec
7:30 a.m. - 9:00 p.m.YWG-ORD
13h 30m1 stop
C$ 195
Find Deal
Mon, 18 Nov
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 315United Airlines
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Thu, 9 Jan
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
C$ 322Air Canada
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Thu, 9 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 324Air Canada
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Fri, 10 Jan
12:45 p.m. - 9:15 p.m.YWG-ORD
8h 30m2 stops
C$ 331Delta
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Sat, 11 Jan
12:20 p.m. - 9:55 a.m.YWG-ORD
21h 35m2 stops
C$ 368WestJet
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Fri, 10 Jan
5:00 a.m. - 12:55 p.m.YWG-ORD
7h 55m2 stops
C$ 375Delta
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Thu, 9 Jan
5:45 p.m. - 10:14 p.m.YWG-ORD
4h 29m1 stop
C$ 476WestJet
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Sun, 17 Nov
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
C$ 481United Airlines
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Mon, 18 Nov
8:15 p.m. - 2:41 p.m.YWG-ORD
18h 26m2 stops
9:55 p.m. - 3:10 p.m.ORD-YWG
17h 15m1 stop
C$ 932
Find Deal
Sat, 9 Nov - Mon, 11 Nov
7:15 a.m. - 7:43 p.m.YWG-ORD
12h 28m1 stop
5:00 a.m. - 9:09 p.m.ORD-YWG
16h 09m2 stops
C$ 1,024
Find Deal
Thu, 7 Nov - Tue, 12 Nov
7:15 a.m. - 7:43 p.m.YWG-ORD
12h 28m1 stop
9:55 p.m. - 3:10 p.m.ORD-YWG
17h 15m1 stop
C$ 1,075
Find Deal
Thu, 7 Nov - Mon, 11 Nov
11:35 a.m. - 6:41 p.m.YWG-ORD
31h 06m3 stops
9:11 p.m. - 9:09 p.m.ORD-YWG
23h 58m3 stops
C$ 1,250
Find Deal
Sat, 9 Nov - Mon, 11 Nov
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
6:38 p.m. - 8:28 a.m.ORD-YWG
13h 50m1 stop
C$ 1,287Air Canada
Find Deal
Thu, 7 Nov - Mon, 11 Nov
12:15 p.m. - 7:32 p.m.YWG-ORD
7h 17m1 stop
7:20 a.m. - 4:18 p.m.ORD-YWG
8h 58m1 stop
C$ 1,294Air Canada
Find Deal
Sat, 9 Nov - Sun, 10 Nov
5:00 a.m. - 9:05 p.m.YWG-ORD
16h 05m2 stops
6:00 a.m. - 11:27 p.m.ORD-YWG
17h 27m1 stop
C$ 1,333WestJet
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Wed, 6 Nov - Sun, 10 Nov
8:45 a.m. - 4:21 p.m.YWG-ORD
31h 36m2 stops
6:00 a.m. - 11:31 a.m.ORD-YWG
5h 31m1 stop
C$ 1,383WestJet
Find Deal
Thu, 7 Nov - Sun, 10 Nov
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 1,397United Airlines
Find Deal
Thu, 7 Nov - Mon, 11 Nov
12:15 p.m. - 7:32 p.m.YWG-ORD
7h 17m1 stop
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 1,404United Airlines
Find Deal
Sat, 9 Nov - Mon, 11 Nov
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 561United Airlines
Find Deal
Mon, 3 Feb - Tue, 4 Feb
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 579Air Canada
Find Deal
Sun, 22 Dec - Tue, 31 Dec
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 596Air Canada
Find Deal
Thu, 28 Nov - Thu, 5 Dec
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 609United Airlines
Find Deal
Tue, 26 Nov - Sat, 7 Dec
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 615United Airlines
Find Deal
Mon, 23 Dec - Tue, 7 Jan
2:15 p.m. - 4:36 p.m.YWG-ORD
2h 21mdirect
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
C$ 651Air Canada
Find Deal
Wed, 9 Apr - Sat, 24 May
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 660United Airlines
Find Deal
Mon, 3 Feb - Sun, 9 Feb
2:15 p.m. - 4:36 p.m.YWG-ORD
2h 21mdirect
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
C$ 671United Airlines
Find Deal
Sat, 22 Mar - Mon, 31 Mar
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:52 p.m. - 3:28 p.m.ORD-YWG
2h 36mdirect
C$ 693Air Canada
Find Deal
Tue, 10 Dec - Thu, 12 Dec
2:15 p.m. - 4:36 p.m.YWG-ORD
2h 21mdirect
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
C$ 767Air Canada
Find Deal
Sat, 22 Mar - Tue, 1 Apr

United Airlines flights from Winnipeg to Chicago O'Hare Intl Airport

Our best United Airlines deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
United Airlines
3 Feb
YWG2:15 p.m.Winnipeg
2h 36m
ORD4:51 p.m.Chicago O'Hare Intl
4 Feb
ORD12:56 p.m.Chicago O'Hare Intl
2h 32m
YWG3:28 p.m.Winnipeg
United Airlines
10 Dec
YWG2:15 p.m.Winnipeg
2h 30m
ORD4:45 p.m.Chicago O'Hare Intl
12 Dec
ORD7:10 a.m.Chicago O'Hare Intl
6h 17m
1 stop
YWG1:27 p.m.Winnipeg
United Airlines
22 Dec
YWG2:15 p.m.Winnipeg
2h 36m
ORD4:51 p.m.Chicago O'Hare Intl
31 Dec
ORD2:05 p.m.Chicago O'Hare Intl
6h 53m
1 stop
YWG8:58 p.m.Winnipeg

Air Canada flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Air Canada deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Air Canada
3 Feb
YWG7:45 a.m.Winnipeg
7h 00m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
9 Feb
ORD7:20 a.m.Chicago O'Hare Intl
9h 04m
1 stop
YWG4:24 p.m.Winnipeg
Air Canada
22 Mar
YWG6:45 a.m.Winnipeg
6h 21m
1 stop
ORD1:06 p.m.Chicago O'Hare Intl
1 Apr
ORD9:03 a.m.Chicago O'Hare Intl
7h 21m
1 stop
YWG4:24 p.m.Winnipeg
Air Canada
16 Jan
YWG7:45 a.m.Winnipeg
7h 00m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
19 Jan
ORD7:10 a.m.Chicago O'Hare Intl
6h 17m
1 stop
YWG1:27 p.m.Winnipeg

How to get the cheapest flight ticket from Winnipeg to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

January. The cheapest time of year to fly to Chicago O'Hare Intl Airport from Winnipeg is January. The most expensive is May.

What is the cheapest day to depart Winnipeg for Chicago O'Hare Intl Airport?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Friday

When is the cheapest time to fly from Winnipeg to Chicago O'Hare Intl Airport?

In the evening. Winnipeg to Chicago O'Hare Intl Airport flights are approximately 27% more expensive in the afternoon than in the evening

What is the cheapest airline that flies to Chicago O'Hare Intl Airport from Winnipeg?

Delta. Delta, Air Canada, and United Airlines are the most popular carriers operating from Winnipeg to Chicago O'Hare Intl Airport

How far in advance should you book Winnipeg to Chicago O'Hare Intl Airport flights?

43 days before. The cheapest time to buy a flight from Winnipeg to Chicago O'Hare Intl Airport is approximately 43 days to departure

How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per day?

3 flights are operational weekly from Winnipeg to Chicago O'Hare Intl Airport as of November 2024. The most popular departure time for this route is 2:00p.m., with 100% of flights per day taking off in the afternoon.

How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per week?

21 flights are operational weekly from Winnipeg to Chicago O'Hare Intl Airport as of November 2024. The most popular departure day for this route is Sunday, with 14% of flights per week taking off on this day.

Can stopping save me money on Winnipeg to Chicago O'Hare Intl Airport flights?

You could potentially save up to 39% on your flight if you consider stops on a Winnipeg to Chicago O'Hare Intl Airport flight.

How have Winnipeg to Chicago O'Hare Intl Airport flight prices changed over time?

As of November 2024, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 0% more expensive when compared to flights at the same time last year.

When to book flights from Winnipeg to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Chicago O'Hare Intl Airport (YWG to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago O'Hare Intl Airport

Best price found

C$ 191

Fastest flight time

2h 21m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is C$ 191. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 470.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 21m
Direct flights go from Winnipeg to Chicago O'Hare Intl Airport every day.

  • How far is Winnipeg to Chicago O'Hare Intl by plane?

    Winnipeg and Chicago O'Hare Intl are 1130.2 km apart from one another. Flights usually cover this in 2h 21m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Winnipeg to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Winnipeg to Chicago O'Hare Intl Airport?


Best airlines flying from Winnipeg to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Winnipeg to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 457Free CancellationRating
7.0
8,123 reviews
Search Air Canada flights
DeltaPriceFrom C$ 483Free CancellationRating
8.0
8,829 reviews
Search Delta flights
WestJetPriceFrom C$ 513Free CancellationRating
7.3
2,803 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 550Free CancellationRating
7.4
9,226 reviews
Search United Airlines flights
  • United Airlines Flights From Winnipeg to Chicago O'Hare Intl Airport

    United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 7 times per week, with 9,226 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Winnipeg to Chicago O'Hare Intl Airport in the last 72 hours was C$ 394 (round-trip), much lower than the average airfare cost of C$ 524 for United Airlines flights on this route.

  • Air Canada Flights From Winnipeg to Chicago O'Hare Intl Airport

    Air Canada is also a popular choice for this route. Air Canada flight deals for Winnipeg to Chicago O'Hare Intl Airport start from as low as C$ 328 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 492. Air Canada operates 7 flights to Chicago O'Hare Intl Airport from Winnipeg in an average week. Users have rated it 7.0/10 across 8,123 reviews.


Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Winnipeg to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?

All flight searches from Winnipeg to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Winnipeg to Chicago?

Once you have performed a search for Winnipeg to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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