Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from $79

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 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.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? 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.
Search flight deals

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.
Multiple Airlines Logo
6:20 am - 3:07 pm
ORD
-
YWG
8h 47m1 stop
Multiple Airlines Logo
4:10 pm - 4:51 pm
YWG
-
ORD
24h 41m2 stops
$218Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
4:41 pm - 3:07 pm
ORD
-
YWG
22h 26m1 stop
Multiple Airlines Logo
9:00 pm - 1:37 pm
YWG
-
ORD
16h 37m2 stops
$235Multiple Airlines
Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
6:20 am - 3:07 pm
ORD
-
YWG
8h 47m1 stop
Multiple Airlines Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
$242Multiple Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
5:40 am - 3:07 pm
ORD
-
YWG
9h 27m1 stop
Multiple Airlines Logo
9:00 pm - 1:58 pm
YWG
-
ORD
16h 58m2 stops
$244Multiple Airlines
Fri, Jan 30 - Mon, Feb 2
WestJet Logo
2:20 pm - 10:41 pm
ORD
-
YWG
8h 21m1 stop
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
$247WestJet
Fri, Jan 30 - Mon, Feb 2
Multiple Airlines Logo
4:41 pm - 3:07 pm
ORD
-
YWG
22h 26m1 stop
Multiple Airlines Logo
9:00 pm - 10:46 pm
YWG
-
ORD
25h 46m2 stops
$254Multiple Airlines
Thu, Jan 15 - Thu, Jan 22
Multiple Airlines Logo
4:41 pm - 3:07 pm
ORD
-
YWG
22h 26m1 stop
Multiple Airlines Logo
9:00 pm - 1:35 pm
YWG
-
ORD
16h 35m1 stop
$302Multiple Airlines
Thu, Jan 15 - Thu, Jan 22
Multiple Airlines Logo
11:44 am - 3:07 pm
ORD
-
YWG
27h 23m1 stop
Multiple Airlines Logo
7:30 am - 10:24 pm
YWG
-
ORD
14h 54m1 stop
$313Multiple Airlines
Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
3:22 pm - 12:41 am
ORD
-
YWG
33h 19m3 stops
Multiple Airlines Logo
8:00 am - 7:38 pm
YWG
-
ORD
11h 38m1 stop
$320Multiple Airlines
Fri, Jan 23 - Mon, Jan 26
WestJet Logo
2:20 pm - 10:41 pm
ORD
-
YWG
8h 21m1 stop
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
$327WestJet
Fri, Jan 30 - Mon, Feb 2

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
Jan 15
ORD9:10 amChicago O'Hare Intl
2h 47m
YWG11:57 amWinnipeg
Jan 22
YWG8:00 amWinnipeg
9h 08m
1 stop
ORD5:08 pmChicago O'Hare Intl
$487
Find similar
Air Canada
Jan 15
ORD9:10 amChicago O'Hare Intl
2h 47m
YWG11:57 amWinnipeg
Jan 22
YWG2:20 pmWinnipeg
2h 43m
ORD5:03 pmChicago O'Hare Intl
$543
Find similar
Air Canada
Jan 30
ORD9:10 amChicago O'Hare Intl
2h 47m
YWG11:57 amWinnipeg
Feb 2
YWG5:30 amWinnipeg
7h 31m
1 stop
ORD1:01 pmChicago O'Hare Intl
$597
Find similar

Porter Airlines flights from Chicago O'Hare Intl Airport to Winnipeg

Our best Porter Airlines deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
Porter Airlines
Apr 23
ORD8:00 amChicago O'Hare Intl
15h 35m
1 stop
YWG11:35 pmWinnipeg
Apr 28
YWG12:10 pmWinnipeg
7h 25m
1 stop
ORD7:35 pmChicago O'Hare Intl
$540
Find similar
Porter Airlines
Apr 23
ORD8:00 amChicago O'Hare Intl
27h 13m
2 stops
YWG11:13 amWinnipeg
Apr 28
YWG6:00 amWinnipeg
8h 05m
1 stop
ORD2:05 pmChicago O'Hare Intl
$586
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 December 4, 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 1/16

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

Fri 1/23

4:10 pm-4:51 pm

2 stops24h 41m

$218

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/17

4:41 pm-3:07 pm

1 stop22h 26m

Winnipeg

Sat 1/24

9:00 pm-1:37 pm

2 stops16h 37m

$235

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/16

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

Fri 1/23

6:15 am-1:35 pm

1 stop7h 20m

$242

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/30

5:40 am-3:07 pm

1 stop9h 27m

Winnipeg

Mon 2/2

9:00 pm-1:58 pm

2 stops16h 58m

$244

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/30

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Mon 2/2

6:15 am-1:35 pm

1 stop7h 20m

$247

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/15

4:41 pm-3:07 pm

1 stop22h 26m

Winnipeg

Thu 1/22

9:00 pm-10:46 pm

2 stops25h 46m

$254

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/15

4:41 pm-3:07 pm

1 stop22h 26m

Winnipeg

Thu 1/22

9:00 pm-1:35 pm

1 stop16h 35m

$302

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 12/11

11:44 am-3:07 pm

1 stop27h 23m

Winnipeg

Sun 12/14

7:30 am-10:24 pm

1 stop14h 54m

$313

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/23

3:22 pm-12:41 am

3 stops33h 19m

Winnipeg

Mon 1/26

8:00 am-7:38 pm

1 stop11h 38m

$320

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/30

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Mon 2/2

6:15 am-1:35 pm

1 stop7h 20m

$327

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Thursday 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 $645.

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 $635 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?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Winnipeg.

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

$680

Fastest flight time

2h 24m

Direct flights

Tue, Wed, 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 $680
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 Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Air Canada.
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 2h 47m.

  • 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
3,193 reviews
Search WestJet flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
10,500 reviews
Search Air Canada flights
United AirlinesPriceFrom $415Free CancellationRating
7.4
9,066 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 $415 round-trip, up to an average price of $629. Our users have rated United Airlines at 7.4/10.

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

    Across 10,500 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
Selkirk

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.

An easier way to manage your Winnipeg 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 1/3
Sat 1/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada