Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 225

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 10/1. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? Instantly customize your results
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.
11:35 a.m. - 9:37 a.m.YWG-ORD
22h 02m2 stops
5:00 a.m. - 7:10 p.m.ORD-YWG
14h 10m2 stops
C$ 473
Find Deal
Mon, 9 Dec - Tue, 17 Dec
12:30 p.m. - 4:44 p.m.YWG-ORD
28h 14m1 stop
5:30 p.m. - 11:01 p.m.ORD-YWG
29h 31m1 stop
C$ 480WestJet
Find Deal
Wed, 7 May - Wed, 14 May
7:30 a.m. - 12:33 a.m.YWG-ORD
17h 03m2 stops
6:33 p.m. - 5:30 p.m.ORD-YWG
22h 57m3 stops
C$ 496
Find Deal
Fri, 13 Dec - Sun, 15 Dec
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
C$ 501Air Canada
Find Deal
Fri, 31 Jan - Tue, 22 Apr
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
10:40 a.m. - 5:18 p.m.ORD-YWG
6h 38m1 stop
C$ 510Air Canada
Find Deal
Sun, 26 Jan - Sat, 26 Apr
12:25 p.m. - 5:30 a.m.YWG-ORD
17h 05m3 stops
5:11 p.m. - 3:10 p.m.ORD-YWG
21h 59m2 stops
C$ 526
Find Deal
Sat, 7 Dec - Tue, 10 Dec
2:15 p.m. - 4:36 p.m.YWG-ORD
2h 21mdirect
7:15 a.m. - 1:03 p.m.ORD-YWG
5h 48m1 stop
C$ 584United Airlines
Find Deal
Sat, 5 Apr - Sun, 13 Apr
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
9:50 a.m. - 5:18 p.m.ORD-YWG
7h 28m1 stop
C$ 598United Airlines
Find Deal
Tue, 14 Jan - Sun, 16 Feb
12:35 p.m. - 8:28 p.m.YWG-ORD
7h 53m2 stops
6:20 a.m. - 11:45 a.m.ORD-YWG
5h 25m1 stop
C$ 658Delta
Find Deal
Fri, 13 Dec - Sun, 15 Dec
5:00 a.m. - 4:13 p.m.YWG-ORD
11h 13m2 stops
7:10 a.m. - 3:08 p.m.ORD-YWG
7h 58m1 stop
C$ 676Delta
Find Deal
Tue, 28 Jan - Tue, 22 Apr
7:30 a.m. - 10:30 p.m.YWG-ORD
15h 00m1 stop
C$ 225
Find Deal
Fri, 10 Jan
6:20 a.m. - 7:08 p.m.YWG-ORD
12h 48m2 stops
C$ 231
Find Deal
Fri, 17 Jan
7:45 a.m. - 2:45 p.m.YWG-ORD
7h 00m1 stop
C$ 284Air Canada
Find Deal
Wed, 29 Jan
7:30 a.m. - 1:11 p.m.YWG-ORD
5h 41m1 stop
C$ 293Air Canada
Find Deal
Wed, 15 Jan
6:55 a.m. - 11:59 p.m.YWG-ORD
17h 04m2 stops
C$ 298Delta
Find Deal
Tue, 14 Jan
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
C$ 319United Airlines
Find Deal
Thu, 9 Jan
12:45 p.m. - 8:53 p.m.YWG-ORD
8h 08m2 stops
C$ 336Delta
Find Deal
Mon, 13 Jan
4:30 p.m. - 11:10 p.m.YWG-ORD
6h 40m1 stop
C$ 340United Airlines
Find Deal
Thu, 19 Dec
6:00 a.m. - 9:58 p.m.YWG-ORD
15h 58m2 stops
C$ 391WestJet
Find Deal
Wed, 29 Jan
5:00 a.m. - 4:40 p.m.YWG-ORD
11h 40m2 stops
C$ 511WestJet
Find Deal
Tue, 24 Dec
11:35 a.m. - 6:31 p.m.YWG-ORD
30h 56m3 stops
7:39 p.m. - 7:02 p.m.ORD-YWG
23h 23m2 stops
C$ 1,228
Find Deal
Fri, 22 Nov - Sun, 24 Nov
4:00 p.m. - 8:03 p.m.YWG-ORD
28h 03m2 stops
7:39 p.m. - 7:02 p.m.ORD-YWG
23h 23m2 stops
C$ 1,252
Find Deal
Fri, 22 Nov - Sun, 24 Nov
8:30 a.m. - 5:09 p.m.YWG-ORD
8h 39m1 stop
9:14 p.m. - 8:28 a.m.ORD-YWG
11h 14m1 stop
C$ 1,284Air Canada
Find Deal
Fri, 22 Nov - Mon, 25 Nov
4:00 p.m. - 10:56 a.m.YWG-ORD
18h 56m1 stop
7:39 p.m. - 7:02 p.m.ORD-YWG
23h 23m2 stops
C$ 1,351
Find Deal
Fri, 22 Nov - Sun, 24 Nov
11:35 a.m. - 6:31 p.m.YWG-ORD
30h 56m3 stops
8:58 p.m. - 8:11 a.m.ORD-YWG
35h 13m3 stops
C$ 1,369
Find Deal
Fri, 22 Nov - Sun, 24 Nov
8:45 a.m. - 10:43 p.m.YWG-ORD
13h 58m2 stops
3:45 p.m. - 11:26 a.m.ORD-YWG
19h 41m2 stops
C$ 1,429WestJet
Find Deal
Fri, 22 Nov - Mon, 25 Nov
7:30 a.m. - 2:25 p.m.YWG-ORD
6h 55m1 stop
7:05 a.m. - 4:55 p.m.ORD-YWG
9h 50m2 stops
C$ 1,474Delta
Find Deal
Fri, 22 Nov - Mon, 25 Nov
6:55 a.m. - 4:52 p.m.YWG-ORD
9h 57m1 stop
12:25 p.m. - 11:41 a.m.ORD-YWG
23h 16m1 stop
C$ 1,548WestJet
Find Deal
Fri, 22 Nov - Sun, 24 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$ 1,559United Airlines
Find Deal
Fri, 22 Nov - Sun, 24 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$ 2,082Air Canada
Find Deal
Fri, 22 Nov - Mon, 25 Nov
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
C$ 501Air Canada
Find Deal
Fri, 31 Jan - Sat, 26 Apr
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$ 545Air Canada
Find Deal
Wed, 23 Apr - Wed, 30 Apr
2:15 p.m. - 4:51 p.m.YWG-ORD
2h 36mdirect
1:00 p.m. - 3:24 p.m.ORD-YWG
2h 24mdirect
C$ 587
Find Deal
Wed, 29 Jan - Wed, 23 Apr
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$ 588Air Canada
Find Deal
Tue, 1 Apr - Tue, 8 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$ 594Air Canada
Find Deal
Tue, 21 Jan - Tue, 28 Jan
2:15 p.m. - 4:45 p.m.YWG-ORD
2h 30mdirect
12:56 p.m. - 3:28 p.m.ORD-YWG
2h 32mdirect
C$ 602United Airlines
Find Deal
Wed, 18 Dec - Wed, 25 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$ 622United Airlines
Find Deal
Sat, 5 Apr - Sun, 13 Apr
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$ 637Air Canada
Find Deal
Sat, 14 Dec - Wed, 18 Dec
2:15 p.m. - 4:37 p.m.YWG-ORD
2h 22mdirect
12:58 p.m. - 3:28 p.m.ORD-YWG
2h 30mdirect
C$ 638United Airlines
Find Deal
Wed, 26 Mar - Sat, 29 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$ 652United Airlines
Find Deal
Sat, 14 Dec - Wed, 18 Dec

WestJet flights from Winnipeg to Chicago O'Hare Intl Airport

Our best WestJet deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
WestJet
7 May
YWG12:30 p.m.Winnipeg
28h 14m
1 stop
ORD4:44 p.m.Chicago O'Hare Intl
14 May
ORD5:30 p.m.Chicago O'Hare Intl
29h 31m
1 stop
YWG11:01 p.m.Winnipeg
WestJet
7 May
YWG12:30 p.m.Winnipeg
28h 14m
1 stop
ORD4:44 p.m.Chicago O'Hare Intl
14 May
ORD7:00 a.m.Chicago O'Hare Intl
8h 58m
2 stops
YWG3:58 p.m.Winnipeg
WestJet
18 Mar
YWG5:00 a.m.Winnipeg
8h 03m
2 stops
ORD1:03 p.m.Chicago O'Hare Intl
21 Mar
ORD12:30 p.m.Chicago O'Hare Intl
12h 04m
2 stops
YWG12:34 a.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
31 Jan
YWG7:45 a.m.Winnipeg
7h 00m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
22 Apr
ORD1:00 p.m.Chicago O'Hare Intl
2h 24m
YWG3:24 p.m.Winnipeg
Air Canada
26 Jan
YWG7:45 a.m.Winnipeg
7h 00m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
26 Apr
ORD10:40 a.m.Chicago O'Hare Intl
6h 38m
1 stop
YWG5:18 p.m.Winnipeg
Air Canada
23 Apr
YWG7:45 a.m.Winnipeg
7h 09m
1 stop
ORD2:54 p.m.Chicago O'Hare Intl
30 Apr
ORD7:20 a.m.Chicago O'Hare Intl
9h 04m
1 stop
YWG4:24 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 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?

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

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

At noon. Winnipeg to Chicago O'Hare Intl Airport flights are approximately 28% more expensive in the afternoon than at noon

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

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

You could potentially save up to 20% 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 35% 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$ 225

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$ 225. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 473.
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$ 395Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
DeltaPriceFrom C$ 485Free CancellationRating
8.0
8,756 reviews
Search Delta flights
WestJetPriceFrom C$ 515Free CancellationRating
7.3
2,811 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 552Free CancellationRating
7.4
9,171 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 9,171 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$ 282 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 481. 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 8,237 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.


An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 25/11
Mon 2/12
Email me momondo's favourite deals

Find better results for your trip to Chicago