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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from $161

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 1/10. 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.
11:35 am - 9:37 amYWG-ORD
22h 02m2 stops
5:00 am - 7:10 pmORD-YWG
14h 10m2 stops
Mon, Dec 9 - Tue, Dec 17
12:30 pm - 4:44 pmYWG-ORD
28h 14m1 stop
5:30 pm - 11:01 pmORD-YWG
29h 31m1 stop
$343WestJet
Find Deal
Wed, May 7 - Wed, May 14
7:30 am - 12:33 amYWG-ORD
17h 03m2 stops
6:33 pm - 5:30 pmORD-YWG
22h 57m3 stops
Fri, Dec 13 - Sun, Dec 15
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$358Air Canada
Find Deal
Fri, Jan 31 - Tue, Apr 22
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
10:40 am - 5:18 pmORD-YWG
6h 38m1 stop
$364Air Canada
Find Deal
Sun, Jan 26 - Sat, Apr 26
12:25 pm - 5:30 amYWG-ORD
17h 05m3 stops
5:11 pm - 3:10 pmORD-YWG
21h 59m2 stops
Sat, Dec 7 - Tue, Dec 10
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
5:00 am - 1:03 pmORD-YWG
8h 03m1 stop
$419United Airlines
Find Deal
Wed, Jan 29 - Sun, Apr 20
2:15 pm - 4:37 pmYWG-ORD
2h 22mnonstop
5:00 am - 1:27 pmORD-YWG
8h 27m1 stop
$421United Airlines
Find Deal
Wed, Mar 26 - Sat, Mar 29
12:35 pm - 8:28 pmYWG-ORD
7h 53m2 stops
6:20 am - 11:45 amORD-YWG
5h 25m1 stop
$470Delta
Find Deal
Fri, Dec 13 - Sun, Dec 15
5:00 am - 4:13 pmYWG-ORD
11h 13m2 stops
7:10 am - 3:08 pmORD-YWG
7h 58m1 stop
$483Delta
Find Deal
Tue, Jan 28 - Tue, Apr 22
7:30 am - 10:30 pmYWG-ORD
15h 00m1 stop
Fri, Jan 10
6:20 am - 7:08 pmYWG-ORD
12h 48m2 stops
Fri, Jan 17
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
$203Air Canada
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Wed, Jan 29
7:30 am - 1:11 pmYWG-ORD
5h 41m1 stop
$209Air Canada
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Wed, Jan 15
6:55 am - 11:59 pmYWG-ORD
17h 04m2 stops
$213Delta
Find Deal
Tue, Jan 14
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$228United Airlines
Find Deal
Thu, Jan 9
12:45 pm - 8:53 pmYWG-ORD
8h 08m2 stops
$240Delta
Find Deal
Mon, Jan 13
4:30 pm - 11:10 pmYWG-ORD
6h 40m1 stop
$243United Airlines
Find Deal
Thu, Dec 19
6:00 am - 9:58 pmYWG-ORD
15h 58m2 stops
$279WestJet
Find Deal
Wed, Jan 29
5:00 am - 4:40 pmYWG-ORD
11h 40m2 stops
$365WestJet
Find Deal
Tue, Dec 24
11:35 am - 6:31 pmYWG-ORD
30h 56m3 stops
7:39 pm - 7:02 pmORD-YWG
23h 23m2 stops
Fri, Nov 22 - Sun, Nov 24
4:00 pm - 8:03 pmYWG-ORD
28h 03m2 stops
7:39 pm - 7:02 pmORD-YWG
23h 23m2 stops
Fri, Nov 22 - Sun, Nov 24
8:30 am - 5:09 pmYWG-ORD
8h 39m1 stop
9:14 pm - 8:28 amORD-YWG
11h 14m1 stop
$917Air Canada
Find Deal
Fri, Nov 22 - Mon, Nov 25
4:00 pm - 10:56 amYWG-ORD
18h 56m1 stop
7:39 pm - 7:02 pmORD-YWG
23h 23m2 stops
Fri, Nov 22 - Sun, Nov 24
11:35 am - 6:31 pmYWG-ORD
30h 56m3 stops
8:58 pm - 8:11 amORD-YWG
35h 13m3 stops
Fri, Nov 22 - Sun, Nov 24
8:45 am - 10:43 pmYWG-ORD
13h 58m2 stops
3:45 pm - 11:26 amORD-YWG
19h 41m2 stops
$1,021WestJet
Find Deal
Fri, Nov 22 - Mon, Nov 25
7:30 am - 2:25 pmYWG-ORD
6h 55m1 stop
7:05 am - 4:55 pmORD-YWG
9h 50m2 stops
$1,053Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
6:55 am - 4:52 pmYWG-ORD
9h 57m1 stop
12:25 pm - 11:41 amORD-YWG
23h 16m1 stop
$1,106WestJet
Find Deal
Fri, Nov 22 - Sun, Nov 24
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$1,114United Airlines
Find Deal
Fri, Nov 22 - Sun, Nov 24
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$1,487Air Canada
Find Deal
Fri, Nov 22 - Mon, Nov 25
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$358Air Canada
Find Deal
Fri, Jan 31 - Sat, Apr 26
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$389Air Canada
Find Deal
Wed, Apr 23 - Wed, Apr 30
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
Wed, Jan 29 - Wed, Apr 23
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$420Air Canada
Find Deal
Tue, Apr 1 - Tue, Apr 8
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$424Air Canada
Find Deal
Tue, Jan 21 - Tue, Jan 28
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$430United Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$444United Airlines
Find Deal
Sat, Apr 5 - Sun, Apr 13
2:15 pm - 4:37 pmYWG-ORD
2h 22mnonstop
12:58 pm - 3:28 pmORD-YWG
2h 30mnonstop
$456United Airlines
Find Deal
Wed, Mar 26 - Sat, Mar 29
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$487Air Canada
Find Deal
Wed, Dec 4 - Wed, Dec 11
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$489Air Canada
Find Deal
Fri, Dec 6 - Tue, Dec 10

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
May 7
YWG12:30 pmWinnipeg
28h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
May 14
ORD5:30 pmChicago O'Hare Intl
29h 31m
1 stop
YWG11:01 pmWinnipeg
WestJet
May 7
YWG12:30 pmWinnipeg
28h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
May 14
ORD7:00 amChicago O'Hare Intl
8h 58m
2 stops
YWG3:58 pmWinnipeg
WestJet
Mar 26
YWG6:40 amWinnipeg
8h 15m
1 stop
ORD2:55 pmChicago O'Hare Intl
Mar 29
ORD2:10 pmChicago O'Hare Intl
10h 24m
2 stops
YWG12:34 amWinnipeg

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
Jan 31
YWG7:45 amWinnipeg
7h 00m
1 stop
ORD2:45 pmChicago O'Hare Intl
Apr 22
ORD1:00 pmChicago O'Hare Intl
2h 24m
YWG3:24 pmWinnipeg
Air Canada
Jan 26
YWG7:45 amWinnipeg
7h 00m
1 stop
ORD2:45 pmChicago O'Hare Intl
Apr 26
ORD10:40 amChicago O'Hare Intl
6h 38m
1 stop
YWG5:18 pmWinnipeg
Air Canada
Apr 23
YWG7:45 amWinnipeg
7h 09m
1 stop
ORD2:54 pmChicago O'Hare Intl
Apr 30
ORD7:20 amChicago O'Hare Intl
9h 04m
1 stop
YWG4:24 pmWinnipeg

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. Most expensive is May

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

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

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

In the morning. Winnipeg to Chicago O'Hare Intl Airport flights are approximately 12% more expensive at noon than in the morning

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

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

There are 2 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl Airport 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 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

$161

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 $161. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $338.
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?

    There are 702.3 mi between Winnipeg and Chicago O'Hare Intl. A reasonable flight in good conditions will take 2h 21m.

  • 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 refresh daily.

  • 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?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • 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 $289Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
DeltaPriceFrom $370Free CancellationRating
8.0
8,756 reviews
Search Delta flights
United AirlinesPriceFrom $441Free 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 $441 (round-trip), much lower than the average airfare cost of $533 for United Airlines flights on this route.

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

    Another popular option for Winnipeg to Chicago O'Hare Intl Airport flights is Air Canada (7.0/10, 8,237 ratings). Air Canada flies from Winnipeg to Chicago O'Hare Intl Airport around 7 times per week, with deals starting from $289 round-trip and rising to an average price of around $550.


Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Winnipeg.

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

Flights from Winnipeg to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Winnipeg to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Winnipeg and alert you when they change.


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