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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from $155

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 6/3. 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
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
$228WestJet
lun, mag 25 - mer, mag 27
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
$239WestJet
ven, mag 29 - mer, giu 3
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$256WestJet
ven, apr 24 - dom, apr 26
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
2 stops
$271WestJet
ven, mag 29 - mer, giu 3
WestJet Logo
5:30 pm - 9:35 am
ORD
-
YWG
16h 05m
2 stops
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$283WestJet
lun, mag 25 - mer, mag 27
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
$285WestJet
lun, mag 4 - mer, mag 6
Multiple Airlines Logo
5:01 am - 12:40 am
ORD
-
YWG
19h 39m
2 stops
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$287Multiple Airlines
ven, apr 24 - dom, apr 26
Multiple Airlines Logo
5:05 am - 3:09 pm
ORD
-
YWG
10h 04m
1 stop
Multiple Airlines Logo
2:40 pm - 6:08 am
YWG
-
ORD
15h 28m
2 stops
$292Multiple Airlines
ven, mar 6 - lun, mar 9
WestJet Logo
5:30 pm - 12:00 pm
ORD
-
YWG
18h 30m
2 stops
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
2 stops
$296WestJet
lun, mag 25 - mer, mag 27
WestJet Logo
5:30 pm - 9:20 am
ORD
-
YWG
15h 50m
2 stops
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
2 stops
$299WestJet
ven, mag 29 - mer, giu 3

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
May 25
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
May 27
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$228
WestJet
May 29
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
Jun 3
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$239
WestJet
Apr 24
ORD2:20 pmChicago O'Hare Intl
8h 20m
1 stop
YWG10:40 pmWinnipeg
Apr 26
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$256

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
Feb 19
ORD9:15 amChicago O'Hare Intl
2h 42m
YWG11:57 amWinnipeg
Feb 23
YWG5:30 amWinnipeg
7h 31m
1 stop
ORD1:01 pmChicago O'Hare Intl
$911
Air Canada
Feb 19
ORD9:15 amChicago O'Hare Intl
2h 42m
YWG11:57 amWinnipeg
Feb 23
YWG2:20 pmWinnipeg
2h 25m
ORD4:45 pmChicago O'Hare Intl
$1,005

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 febbraio 12, 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

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun 5/25

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

mer 5/27

7:00 am-4:40 pm

1 stop9h 40m

$228

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven 5/29

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

mer 6/3

7:00 am-4:40 pm

1 stop9h 40m

$239

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven 4/24

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

dom 4/26

7:00 am-4:40 pm

1 stop9h 40m

$256

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven 5/29

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

mer 6/3

7:00 am-4:40 pm

2 stops9h 40m

$271

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun 5/25

5:30 pm-9:35 am

2 stops16h 05m

Winnipeg

mer 5/27

7:00 am-4:40 pm

1 stop9h 40m

$283

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun 5/4

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

mer 5/6

4:55 pm-4:40 pm

1 stop23h 45m

$285

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven 4/24

5:01 am-12:40 am

2 stops19h 39m

Winnipeg

dom 4/26

7:00 am-4:40 pm

1 stop9h 40m

$287

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven 3/6

5:05 am-3:09 pm

1 stop10h 04m

Winnipeg

lun 3/9

2:40 pm-6:08 am

2 stops15h 28m

$292

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun 5/25

5:30 pm-12:00 pm

2 stops18h 30m

Winnipeg

mer 5/27

7:00 am-4:40 pm

2 stops9h 40m

$296

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven 5/29

5:30 pm-9:20 am

2 stops15h 50m

Winnipeg

mer 6/3

7:00 am-4:40 pm

2 stops9h 40m

$299

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 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 $584. 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 $552. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $699 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

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

There is only 1 cabin class 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 71% 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 February 2026, prices for Chicago O'Hare Intl Airport to Winnipeg flights are approximately 63% more expensive 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

$661

Fastest flight time

2h 24m

Direct flights

Every day

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 $661
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

  • 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
3,256 reviews
Search WestJet flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
10,709 reviews
Search Air Canada flights
United AirlinesPriceFrom $263Free CancellationRating
7.4
9,279 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 7 flights/week on average for this route. A good United Airlines flight deal for Chicago O'Hare Intl Airport to Winnipeg starts from $263 round-trip, up to an average price of $643. Our users have rated United Airlines at 7.4/10.

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

    Across 10,709 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Chicago O'Hare Intl Airport to Winnipeg about 7 times each week, with ticket deals ranging from $230 to $552. 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
Portage la Prairie
Selkirk
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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