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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from $113

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Winnipeg departing on 3/2. 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 Chicago O'Hare Intl Airport to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
2:20 pm - 8:06 pmORD-YWG
29h 46m1 stop
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
$251WestJet
Find Deal
Fri, Nov 28 - Fri, Dec 5
Multiple Airlines Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
Multiple Airlines Logo
7:30 am - 8:27 pmYWG-ORD
12h 57m2 stops
$264Multiple Airlines
Find Deal
Fri, Oct 31 - Wed, Nov 5
Multiple Airlines Logo
6:23 pm - 5:26 pmORD-YWG
23h 03m1 stop
Multiple Airlines Logo
9:00 pm - 11:14 amYWG-ORD
14h 14m2 stops
$267Multiple Airlines
Find Deal
Mon, Oct 27 - Mon, Nov 3
Multiple Airlines Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
Multiple Airlines Logo
7:30 am - 10:35 amYWG-ORD
27h 05m1 stop
$296Multiple Airlines
Find Deal
Fri, Oct 31 - Wed, Nov 5
Multiple Airlines Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
Multiple Airlines Logo
7:30 am - 10:49 amYWG-ORD
27h 19m1 stop
$302Multiple Airlines
Find Deal
Mon, Jan 5 - Sun, Jan 11
Multiple Airlines Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
Multiple Airlines Logo
5:00 am - 7:24 pmYWG-ORD
14h 24m2 stops
$313Multiple Airlines
Find Deal
Mon, Jan 5 - Sun, Jan 11
Multiple Airlines Logo
2:20 pm - 8:06 pmORD-YWG
29h 46m1 stop
Multiple Airlines Logo
7:30 am - 11:14 amYWG-ORD
27h 44m2 stops
$322Multiple Airlines
Find Deal
Fri, Nov 28 - Fri, Dec 5
Multiple Airlines Logo
5:11 am - 3:07 pmORD-YWG
9h 56m1 stop
Multiple Airlines Logo
7:30 am - 11:28 pmYWG-ORD
15h 58m2 stops
$328Multiple Airlines
Find Deal
Fri, Nov 7 - Sun, Nov 9
Multiple Airlines Logo
9:00 am - 12:36 amORD-YWG
15h 36m2 stops
Multiple Airlines Logo
8:00 am - 5:04 pmYWG-ORD
9h 04m1 stop
$334Multiple Airlines
Find Deal
Wed, Feb 18 - Tue, Feb 24
WestJet Logo
6:45 am - 7:12 pmORD-YWG
12h 27m2 stops
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
$396WestJet
Find Deal
Thu, Nov 20 - Mon, Nov 24

WestJet flights from Chicago O'Hare Intl Airport to Winnipeg

Our best WestJet deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
WestJet
Nov 28
ORD2:20 pmChicago O'Hare Intl
29h 46m
1 stop
YWG8:06 pmWinnipeg
Dec 5
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
$251
Find similar
WestJet
Nov 20
ORD6:45 amChicago O'Hare Intl
12h 27m
2 stops
YWG7:12 pmWinnipeg
Nov 24
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
$396
Find similar
WestJet
Nov 20
ORD6:45 amChicago O'Hare Intl
12h 27m
2 stops
YWG7:12 pmWinnipeg
Nov 23
YWG12:40 pmWinnipeg
24h 55m
1 stop
ORD1:35 pmChicago O'Hare Intl
$397
Find similar

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

Our best Air Canada deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
Air Canada
Oct 24
ORD7:54 pmChicago O'Hare Intl
2h 39m
YWG10:33 pmWinnipeg
Oct 27
YWG2:20 pmWinnipeg
2h 41m
ORD5:01 pmChicago O'Hare Intl
$1,061
Find similar
Air Canada
Oct 24
ORD7:54 pmChicago O'Hare Intl
2h 39m
YWG10:33 pmWinnipeg
Oct 27
YWG8:00 amWinnipeg
9h 10m
1 stop
ORD5:10 pmChicago O'Hare Intl
$1,063
Find similar
Air Canada
Oct 24
ORD1:01 pmChicago O'Hare Intl
2h 30m
YWG3:31 pmWinnipeg
Oct 27
YWG2:20 pmWinnipeg
2h 41m
ORD5:01 pmChicago O'Hare Intl
$1,115
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 16, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/28

2:20 pm-8:06 pm

1 stop29h 46m

Winnipeg

Fri 12/5

6:15 am-1:35 pm

1 stop7h 20m

$251

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/31

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Wed 11/5

7:30 am-8:27 pm

2 stops12h 57m

$264

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 10/27

6:23 pm-5:26 pm

1 stop23h 03m

Winnipeg

Mon 11/3

9:00 pm-11:14 am

2 stops14h 14m

$267

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/31

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Wed 11/5

7:30 am-10:35 am

1 stop27h 05m

$296

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 1/5

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Sun 1/11

7:30 am-10:49 am

1 stop27h 19m

$302

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 1/5

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Sun 1/11

5:00 am-7:24 pm

2 stops14h 24m

$313

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/28

2:20 pm-8:06 pm

1 stop29h 46m

Winnipeg

Fri 12/5

7:30 am-11:14 am

2 stops27h 44m

$322

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/7

5:11 am-3:07 pm

1 stop9h 56m

Winnipeg

Sun 11/9

7:30 am-11:28 pm

2 stops15h 58m

$328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 2/18

9:00 am-12:36 am

2 stops15h 36m

Winnipeg

Tue 2/24

8:00 am-5:04 pm

1 stop9h 04m

$334

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 11/20

6:45 am-7:12 pm

2 stops12h 27m

Winnipeg

Mon 11/24

6:15 am-1:35 pm

1 stop7h 20m

$396

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Winnipeg from

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

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 Winnipeg?

In general, May is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $230. If you’re not able to fly to Winnipeg in May, then April is your next best option. Flight prices from Chicago O'Hare Intl Airport to Winnipeg during April average around $262.

What is the cheapest day to depart on your flight to Winnipeg?

The cheapest day to depart on your flight to Winnipeg is on a Saturday when prices can be found for as low as $562. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $675.

What is the cheapest time of day to depart on your flight to Winnipeg?

The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $543. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $636 on average. Flights to Winnipeg from Chicago O'Hare Intl Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

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

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

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

You could potentially save up to 62% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Winnipeg flight.

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

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

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

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

Best Price Found

$493

Fastest flight time

2h 24m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Winnipeg

1 airport
The best flight deal from Chicago O'Hare Intl Airport to Winnipeg found on momondo in the last 72 hours is $493
The fastest flight from Chicago O'Hare Intl Airport to Winnipeg takes 2h 24m
Direct flights go from Chicago O'Hare Intl Airport to Winnipeg on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.
There is 1 airport near Winnipeg: Winnipeg (YWG)
Search flight deals

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

    There are 702.3 mi between Chicago O'Hare Intl and Winnipeg. In terms of flight time, this usually takes a little over 8h 21m.

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

    Prices for flights from Chicago O'Hare Intl Airport to Winnipeg Airport refresh daily.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The travel and health documents required for your trip to Winnipeg 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 Winnipeg 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 Chicago O'Hare Intl Airport to Winnipeg?

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

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

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $226Free CancellationRating
7.1
10,306 reviews
Search Air Canada flights
United AirlinesPriceFrom $415Free CancellationRating
7.4
8,982 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago O'Hare Intl Airport to Winnipeg

    United Airlines is one of the most popular airlines flying from Chicago O'Hare Intl Airport to Winnipeg, operating 14 flights/week on average for this route. A good United Airlines flight deal for Chicago O'Hare Intl Airport to Winnipeg starts from $415 round-trip, up to an average price of $618. Our users have rated United Airlines at 7.4/10.

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

    Across 10,306 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Chicago O'Hare Intl Airport to Winnipeg about 14 times each week, with ticket deals ranging from $226 to $585. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Scanterbury
Selkirk
Morden
Portage la Prairie

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Winnipeg for you.

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

Yes. momondo allows you to filter the results for Chicago to Winnipeg flights to just show those with flexible booking policies.

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

Once all potential Chicago to Winnipeg 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 Chicago to Winnipeg right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Winnipeg flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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