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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from $158

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 10/25. 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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0 bags

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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
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$328WestJet
Thu, Oct 1 - Sun, Oct 11
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$362WestJet
Wed, Sep 2 - Sat, Sep 5
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
4:55 pm - 4:40 pm
YWG
-
ORD
23h 45m
1 stop
$365WestJet
Thu, Oct 1 - Sat, Oct 10
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$387WestJet
Wed, Sep 2 - Sat, Sep 5
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$405WestJet
Thu, Oct 15 - Mon, Oct 19
Multiple Airlines Logo
7:00 am - 5:58 pm
ORD
-
YWG
10h 58m
2 stops
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$414Multiple Airlines
Thu, Oct 1 - Sun, Oct 11
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
4:55 pm - 5:42 am
YWG
-
ORD
12h 47m
2 stops
$421Multiple Airlines
Thu, Oct 1 - Sat, Oct 10
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
12:15 pm - 7:29 pm
YWG
-
ORD
7h 14m
1 stop
$425Multiple Airlines
Mon, Jun 29 - Mon, Jul 6
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:20 am - 4:18 pm
YWG
-
ORD
6h 58m
1 stop
$433Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 pm - 8:03 am
YWG
-
ORD
34h 58m
2 stops
$434Multiple Airlines
Thu, Jun 4 - Sun, Jun 7

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
Oct 1
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
Oct 11
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$328
WestJet
Sep 2
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
Sep 5
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$362
WestJet
Oct 1
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
Oct 10
YWG4:55 pmWinnipeg
23h 45m
1 stop
ORD4:40 pmChicago O'Hare Intl
$365

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
May 30
ORD8:40 amChicago O'Hare Intl
15h 09m
2 stops
YWG11:49 pmWinnipeg
Jun 3
YWG7:20 amWinnipeg
12h 56m
2 stops
ORD8:16 pmChicago O'Hare Intl
$830
Air Canada
May 30
ORD9:14 amChicago O'Hare Intl
2h 38m
YWG11:52 amWinnipeg
Jun 6
YWG5:10 amWinnipeg
8h 15m
1 stop
ORD1:25 pmChicago O'Hare Intl
$840
Air Canada
May 27
ORD8:00 pmChicago O'Hare Intl
2h 38m
YWG10:38 pmWinnipeg
Jun 2
YWG8:10 amWinnipeg
6h 45m
1 stop
ORD2:55 pmChicago O'Hare Intl
$861

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 May 17, 2026.
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

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/1

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 10/11

7:00 am-4:40 pm

1 stop9h 40m

$328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/2

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sat 9/5

7:00 am-4:40 pm

1 stop9h 40m

$362

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/1

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sat 10/10

4:55 pm-4:40 pm

1 stop23h 45m

$365

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/2

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sat 9/5

7:00 am-4:40 pm

1 stop9h 40m

$387

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/15

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Mon 10/19

7:00 am-4:40 pm

1 stop9h 40m

$405

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/1

7:00 am-5:58 pm

2 stops10h 58m

Winnipeg

Sun 10/11

7:00 am-4:40 pm

1 stop9h 40m

$414

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/1

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sat 10/10

4:55 pm-5:42 am

2 stops12h 47m

$421

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 6/29

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Mon 7/6

12:15 pm-7:29 pm

1 stop7h 14m

$425
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 6/4

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Thu 6/11

9:20 am-4:18 pm

1 stop6h 58m

$433

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 6/4

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 6/7

9:05 pm-8:03 am

2 stops34h 58m

$434

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 typical price of a round-trip flight between Chicago O'Hare Intl Airport and Winnipeg?

What is the cheapest month to fly to Winnipeg?

In general, March 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 $0. If you’re not able to fly to Winnipeg in March, then January is your next best option. Flight prices from Chicago O'Hare Intl Airport to Winnipeg during January average around $0.

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 Tuesday when prices can be found for as low as $585. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $1,062.

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 $645. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $762 on average. Flights to Winnipeg from Chicago O'Hare Intl Airport in the morning 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

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

You could potentially save up to 51% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Winnipeg flight.

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

As of May 2026, prices for Chicago O'Hare Intl Airport to Winnipeg flights are approximately 46% cheaper when compared to flights at the same time last year.

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

$624

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago O'Hare Intl Airport in the past 72 hours is $624. The best round-trip flight deal from Chicago O'Hare Intl Airport to Winnipeg found on momondo in the last 72 hours is $755.
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 every day.
There is 1 airport in Winnipeg. From Chicago O'Hare Intl Airport there are direct flights to Winnipeg (YWG).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Winnipeg

  • 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 2h 24m.

  • 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
WestJetPriceFrom $156Free CancellationRating
7.2
3,336 reviews
Search WestJet flights
United AirlinesPriceFrom $291Free CancellationRating
7.4
9,730 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 6 flights/week on average for this route. A good United Airlines flight deal for Chicago O'Hare Intl Airport to Winnipeg starts from $291 round-trip, up to an average price of $672. Our users have rated United Airlines at 7.4/10.

Traveling to a place near Winnipeg?

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

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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