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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 198

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 19/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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. - 5:55 a.m.YWG-ORD
22h 25m2 stops
3:56 p.m. - 11:20 p.m.ORD-YWG
31h 24m3 stops
C$ 501
Find Deal
Tue, 21 Jan - Tue, 28 Jan
7:00 p.m. - 8:13 p.m.YWG-ORD
25h 13m2 stops
5:11 a.m. - 10:45 a.m.ORD-YWG
29h 34m2 stops
C$ 510
Find Deal
Tue, 21 Jan - Tue, 28 Jan
5:37 p.m. - 9:58 p.m.YWG-ORD
4h 21m1 stop
6:35 p.m. - 11:55 a.m.ORD-YWG
17h 20m2 stops
C$ 598Delta
Find Deal
Fri, 17 Jan - Fri, 24 Jan
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 605Air Canada
Find Deal
Wed, 29 Jan - Wed, 5 Feb
2:20 p.m. - 4:48 p.m.YWG-ORD
2h 28mdirect
9:15 p.m. - 1:09 p.m.ORD-YWG
15h 54m1 stop
C$ 612United Airlines
Find Deal
Fri, 4 Apr - Mon, 7 Apr
12:45 p.m. - 5:29 p.m.YWG-ORD
4h 44m1 stop
6:45 a.m. - 4:47 p.m.ORD-YWG
10h 02m2 stops
C$ 619Delta
Find Deal
Tue, 21 Jan - Tue, 28 Jan
4:25 p.m. - 12:35 a.m.YWG-ORD
8h 10m1 stop
7:50 p.m. - 1:09 p.m.ORD-YWG
17h 19m1 stop
C$ 621United Airlines
Find Deal
Fri, 4 Apr - Mon, 7 Apr
12:20 p.m. - 8:34 p.m.YWG-ORD
8h 14m2 stops
4:45 p.m. - 9:08 a.m.ORD-YWG
16h 23m1 stop
C$ 626WestJet
Find Deal
Fri, 4 Apr - Mon, 7 Apr
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
7:10 a.m. - 1:27 p.m.ORD-YWG
6h 17m1 stop
C$ 644Air Canada
Find Deal
Fri, 17 Jan - Sun, 19 Jan
12:20 p.m. - 8:34 p.m.YWG-ORD
8h 14m2 stops
4:45 p.m. - 12:08 p.m.ORD-YWG
19h 23m1 stop
C$ 661WestJet
Find Deal
Fri, 4 Apr - Mon, 7 Apr
7:30 a.m. - 10:27 p.m.YWG-ORD
14h 57m1 stop
C$ 198
Find Deal
Sun, 19 Jan
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
C$ 246WestJet
Find Deal
Sat, 31 May
4:25 p.m. - 6:07 a.m.YWG-ORD
13h 42m2 stops
C$ 257
Find Deal
Tue, 11 Feb
7:30 a.m. - 5:55 a.m.YWG-ORD
22h 25m2 stops
C$ 259
Find Deal
Wed, 15 Jan
7:15 a.m. - 2:45 p.m.YWG-ORD
7h 30m1 stop
C$ 341Air Canada
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Tue, 11 Feb
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 371United Airlines
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Wed, 15 Jan
5:37 p.m. - 9:58 p.m.YWG-ORD
4h 21m1 stop
C$ 379Delta
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Wed, 15 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 411United Airlines
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Thu, 9 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 412Air Canada
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Thu, 9 Jan
5:37 p.m. - 9:58 p.m.YWG-ORD
4h 21m1 stop
C$ 421Delta
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Thu, 9 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
8:30 p.m. - 8:28 a.m.ORD-YWG
11h 58m1 stop
C$ 1,042Air Canada
Find Deal
Tue, 24 Dec - Sat, 4 Jan
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 1,079Air Canada
Find Deal
Tue, 24 Dec - Tue, 31 Dec
6:00 a.m. - 10:52 p.m.YWG-ORD
16h 52m2 stops
5:50 p.m. - 11:52 a.m.ORD-YWG
18h 02m1 stop
C$ 1,082WestJet
Find Deal
Wed, 25 Dec - Sat, 4 Jan
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
2:05 p.m. - 8:58 p.m.ORD-YWG
6h 53m1 stop
C$ 1,088Air Canada
Find Deal
Tue, 24 Dec - Tue, 31 Dec
5:00 a.m. - 4:40 p.m.YWG-ORD
11h 40m2 stops
5:50 p.m. - 11:52 a.m.ORD-YWG
18h 02m1 stop
C$ 1,091WestJet
Find Deal
Thu, 26 Dec - Sat, 4 Jan
6:00 a.m. - 10:52 p.m.YWG-ORD
16h 52m2 stops
5:50 p.m. - 11:52 a.m.ORD-YWG
18h 02m1 stop
C$ 1,208WestJet
Find Deal
Tue, 24 Dec - Sat, 4 Jan
12:42 p.m. - 5:09 p.m.YWG-ORD
4h 27m1 stop
7:00 a.m. - 3:34 p.m.ORD-YWG
8h 34m2 stops
C$ 1,352WestJet
Find Deal
Wed, 25 Dec - Thu, 2 Jan
6:55 a.m. - 6:52 p.m.YWG-ORD
11h 57m2 stops
7:05 a.m. - 3:10 p.m.ORD-YWG
8h 05m1 stop
C$ 1,365Delta
Find Deal
Tue, 24 Dec - Wed, 1 Jan
5:00 a.m. - 4:40 p.m.YWG-ORD
11h 40m2 stops
6:20 a.m. - 11:52 a.m.ORD-YWG
5h 32m1 stop
C$ 1,374Delta
Find Deal
Thu, 26 Dec - Fri, 3 Jan
12:42 p.m. - 11:56 p.m.YWG-ORD
11h 14m2 stops
10:05 a.m. - 4:54 p.m.ORD-YWG
6h 49m1 stop
C$ 1,418Delta
Find Deal
Tue, 24 Dec - Fri, 3 Jan
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$ 598Air Canada
Find Deal
Wed, 29 Jan - Wed, 5 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$ 628United Airlines
Find Deal
Sat, 18 Jan - Sat, 25 Jan
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$ 631United Airlines
Find Deal
Fri, 17 Jan - Fri, 24 Jan
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$ 642United Airlines
Find Deal
Fri, 17 Jan - Fri, 24 Jan
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$ 756United Airlines
Find Deal
Tue, 21 Jan - Tue, 28 Jan
2:20 p.m. - 4:48 p.m.YWG-ORD
2h 28mdirect
12:57 p.m. - 3:31 p.m.ORD-YWG
2h 34mdirect
C$ 779United Airlines
Find Deal
Fri, 4 Apr - Mon, 7 Apr
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$ 810Air Canada
Find Deal
Fri, 10 Jan - Sun, 12 Jan
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$ 812Air Canada
Find Deal
Fri, 10 Jan - Sun, 12 Jan
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$ 1,002Air Canada
Find Deal
Fri, 17 Jan - Fri, 24 Jan

Delta flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Delta deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Delta
17 Jan
YWG5:37 p.m.Winnipeg
4h 21m
1 stop
ORD9:58 p.m.Chicago O'Hare Intl
24 Jan
ORD6:35 p.m.Chicago O'Hare Intl
17h 20m
2 stops
YWG11:55 a.m.Winnipeg
Delta
21 Jan
YWG12:45 p.m.Winnipeg
4h 44m
1 stop
ORD5:29 p.m.Chicago O'Hare Intl
28 Jan
ORD6:45 a.m.Chicago O'Hare Intl
10h 02m
2 stops
YWG4:47 p.m.Winnipeg
Delta
18 Jan
YWG12:45 p.m.Winnipeg
4h 44m
1 stop
ORD5:29 p.m.Chicago O'Hare Intl
3 Sep
ORD8:55 a.m.Chicago O'Hare Intl
11h 13m
2 stops
YWG8:08 p.m.Winnipeg

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
4 Apr
YWG2:20 p.m.Winnipeg
2h 28m
ORD4:48 p.m.Chicago O'Hare Intl
7 Apr
ORD9:15 p.m.Chicago O'Hare Intl
15h 54m
1 stop
YWG1:09 p.m.Winnipeg
United Airlines
4 Apr
YWG4:25 p.m.Winnipeg
8h 10m
1 stop
ORD12:35 a.m.Chicago O'Hare Intl
7 Apr
ORD7:50 p.m.Chicago O'Hare Intl
17h 19m
1 stop
YWG1:09 p.m.Winnipeg
United Airlines
18 Jan
YWG2:15 p.m.Winnipeg
2h 36m
ORD4:51 p.m.Chicago O'Hare Intl
25 Jan
ORD12:56 p.m.Chicago O'Hare Intl
2h 32m
YWG3:28 p.m.Winnipeg

See travel insights to Chicago from

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 to Chicago O'Hare Intl Airport?

In general, January is the cheapest month to fly from Winnipeg to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 575. The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around C$ 637.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as C$ 662. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago O'Hare Intl Airport for around C$ 1,017.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Winnipeg to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 731. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 998 on average. Flights to Chicago O'Hare Intl Airport from Winnipeg in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Winnipeg to Chicago O'Hare Intl flight route?

Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago O'Hare Intl flight prices

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

The best time to book a flight to Chicago O'Hare Intl Airport from Winnipeg is 43 days out, which is when prices tend to be around C$ 743. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Winnipeg for as low as C$ 539 on momondo.

What cabin class options are available on Winnipeg to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 24% 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 December 2024, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 14% 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$ 198

Fastest flight time

2h 28m

Direct flights

Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is C$ 198. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 501.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 28m
Direct flights go from Winnipeg to Chicago O'Hare Intl Airport on Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Air Canada.

  • 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 28m, 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$ 395Free CancellationRating
7.0
8,413 reviews
Search Air Canada flights
DeltaPriceFrom C$ 498Free CancellationRating
8.0
8,597 reviews
Search Delta flights
WestJetPriceFrom C$ 528Free CancellationRating
7.2
2,814 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 567Free CancellationRating
7.4
9,035 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 9,028 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$ 275 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 8,403 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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