How many flights depart from Chicago O'Hare Intl Airport to Winnipeg on average per day?

3 flights are operational daily from Chicago O'Hare Intl Airport to Winnipeg as of November 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

What is the cheapest airline that flies from Chicago O'Hare Intl to Winnipeg?

Porter Airlines is the most popular carrier operating from Chicago O'Hare Intl to Winnipeg

How many flights depart from Chicago O'Hare Intl Airport to Winnipeg on average per week?

21 flights are operational weekly from Chicago O'Hare Intl Airport to Winnipeg as of November 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

What airlines fly to Winnipeg?

United Airlines, WestJet and Air Canada are the top three most popular airlines that fly to Winnipeg from Chicago O'Hare Intl Airport according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Winnipeg. Keep in mind that there are 3 different airlines that fly to Winnipeg on a routine basis, so you have a few additional options to choose from.

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?

There are 3 operators available for flights from Chicago O'Hare Intl Airport to Winnipeg Airport as of November 2026.

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.

$177 Cheap Flights from Chicago O'Hare Intl Airport to Winnipeg in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago O'Hare Intl Airport to Winnipeg

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 2:40 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 40m1 stop Atlanta Hartsfield-Jackson

7:00 am - 11:50 amYWG Winnipeg-ORD Chicago O'Hare Intl

29h 50m1 stop Atlanta Hartsfield-Jackson

$385Multiple Airlines

Fri, Feb 5 - Mon, Feb 8

6:00 am - 2:40 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 40m1 stop Atlanta Hartsfield-Jackson

7:00 am - 12:18 amYWG Winnipeg-ORD Chicago O'Hare Intl

18h 18m1 stop Atlanta Hartsfield-Jackson

$395Multiple Airlines

Fri, Jan 15 - Mon, Jan 18

1:33 pm - 2:40 pmORD Chicago O'Hare Intl-YWG Winnipeg

24h 07m1 stop Atlanta Hartsfield-Jackson

7:00 am - 12:18 amYWG Winnipeg-ORD Chicago O'Hare Intl

18h 18m1 stop Atlanta Hartsfield-Jackson

$395Multiple Airlines

Thu, Jan 14 - Mon, Jan 18

6:20 am - 11:31 amORD Chicago O'Hare Intl-YWG Winnipeg

4h 11m1 stop Minneapolis St Paul

5:45 pm - 9:35 pmYWG Winnipeg-ORD Chicago O'Hare Intl

4h 50m1 stop Minneapolis St Paul

$527WestJet

Thu, Dec 3 - Sun, Dec 6

6:20 am - 11:31 amORD Chicago O'Hare Intl-YWG Winnipeg

4h 11m1 stop Minneapolis St Paul

9:35 pm - 5:06 pmYWG Winnipeg-ORD Chicago O'Hare Intl

20h 31m2 stops Calgary Atlanta Hartsfield-Jackson

$551WestJet

Thu, Dec 3 - Sun, Dec 6

9:59 am - 11:31 amORD Chicago O'Hare Intl-YWG Winnipeg

24h 32m1 stop Minneapolis St Paul

9:35 pm - 5:06 pmYWG Winnipeg-ORD Chicago O'Hare Intl

20h 31m2 stops Calgary Atlanta Hartsfield-Jackson

$572WestJet

Sat, Dec 12 - Sun, Dec 13

2:15 pm - 3:09 pmORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

1:45 pm - 12:53 pmYWG Winnipeg-ORD Chicago O'Hare Intl

24h 08m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$746United Airlines

Tue, Jan 19 - Wed, Feb 3

6:17 pm - 1:24 amORD Chicago O'Hare Intl-YWG Winnipeg

6h 07m1 stop Toronto Pearson Intl

8:15 am - 3:38 pmYWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

$764Air Canada

Wed, Jan 20 - Sat, Jan 23

6:17 pm - 1:24 amORD Chicago O'Hare Intl-YWG Winnipeg

6h 07m1 stop Toronto Pearson Intl

12:05 pm - 5:43 pmYWG Winnipeg-ORD Chicago O'Hare Intl

6h 38m1 stop Toronto Pearson Intl

$764Air Canada

Wed, Jan 20 - Sat, Jan 23

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

3:15 pm - 5:00 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mnonstop

$866United Airlines

Fri, Dec 11 - Sun, Dec 13

Cheap last minute flights

Enter your travel dates to find the best prices.

7:05 am - 12:44 amORD Chicago O'Hare Intl-YWG Winnipeg

16h 39m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

6:15 am - 3:38 pmYWG Winnipeg-ORD Chicago O'Hare Intl

10h 23m1 stop Toronto Pearson Intl

$510Air Canada

Wed, Nov 11 - Thu, Nov 19

6:10 am - 7:55 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 45m1 stop Cancun

10:00 am - 6:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 30m2 stops Regina Minneapolis St Paul

$812Multiple Airlines

Wed, Nov 11 - Thu, Nov 19

6:10 am - 7:55 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 45m1 stop Cancun

7:00 am - 6:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 30m3 stops Calgary Regina Minneapolis St Paul

$812Multiple Airlines

Wed, Nov 11 - Thu, Nov 19

1:05 am - 7:55 pmORD Chicago O'Hare Intl-YWG Winnipeg

17h 50m2 stops Mexico City Benito Juarez Cancun

10:00 am - 6:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 30m2 stops Regina Minneapolis St Paul

$937Multiple Airlines

Tue, Nov 10 - Thu, Nov 19

10:57 am - 7:25 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 28m1 stop Ottawa

3:15 pm - 4:50 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$999Air Canada

Wed, Nov 11 - Thu, Nov 19

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

3:15 pm - 4:50 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$999Air Canada

Wed, Nov 11 - Thu, Nov 19

8:40 am - 9:57 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 17m1 stop Denver Intl

3:15 pm - 4:50 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$1,251United Airlines

Thu, Nov 12 - Tue, Nov 17

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

6:15 am - 1:13 pmYWG Winnipeg-ORD Chicago O'Hare Intl

7h 58m1 stop Toronto Pearson Intl

$1,266United Airlines

Wed, Nov 11 - Mon, Nov 16

7:00 am - 8:50 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 50m2 stops New York LaGuardia Toronto Pearson Intl

9:35 pm - 12:20 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 45m2 stops Calgary Atlanta Hartsfield-Jackson

$1,286WestJet

Wed, Nov 11 - Mon, Nov 16

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

3:15 pm - 4:50 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$1,333United Airlines

Wed, Nov 11 - Mon, Nov 16

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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

Nov 11

ORD7:05 amChicago O'Hare Intl

16h 39m

2 stops

YWG12:44 amWinnipeg

Nov 19

YWG6:15 amWinnipeg

10h 23m

1 stop

ORD3:38 pmChicago O'Hare Intl

$510

Air Canada

Nov 11

ORD10:57 amChicago O'Hare Intl

7h 28m

1 stop

YWG7:25 pmWinnipeg

Nov 19

YWG3:15 pmWinnipeg

2h 35m

ORD4:50 pmChicago O'Hare Intl

$999

Air Canada

Nov 10

ORD10:15 amChicago O'Hare Intl

14h 04m

2 stops

YWG1:19 amWinnipeg

Nov 17

YWG9:40 amWinnipeg

8h 25m

1 stop

ORD5:05 pmChicago O'Hare Intl

$1,097

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

Dec 12

ORD12:15 pmChicago O'Hare Intl

9h 42m

1 stop

YWG10:57 pmWinnipeg

Dec 13

YWG7:00 amWinnipeg

11h 40m

1 stop

ORD5:40 pmChicago O'Hare Intl

$550

Porter Airlines

Nov 22

ORD6:20 pmChicago O'Hare Intl

23h 46m

3 stops

YWG7:06 pmWinnipeg

Nov 25

YWG7:00 amWinnipeg

11h 40m

1 stop

ORD5:40 pmChicago O'Hare Intl

$921

Porter Airlines

Nov 20

ORD8:45 pmChicago O'Hare Intl

13h 57m

1 stop

YWG11:42 amWinnipeg

Nov 21

YWG8:00 pmWinnipeg

13h 39m

1 stop

ORD8:39 amChicago O'Hare Intl

$990

momondo Fare Finder

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 Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/5

6:00 am-2:40 pm

1 stop7h 40m

Winnipeg

Mon 2/8

7:00 am-11:50 am

1 stop29h 50m

$385

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 1/15

6:00 am-2:40 pm

1 stop7h 40m

Winnipeg

Mon 1/18

7:00 am-12:18 am

1 stop18h 18m

$395

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 1/14

1:33 pm-2:40 pm

1 stop24h 07m

Winnipeg

Mon 1/18

7:00 am-12:18 am

1 stop18h 18m

$395

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 12/3

6:20 am-11:31 am

1 stop4h 11m

Winnipeg

Sun 12/6

5:45 pm-9:35 pm

1 stop4h 50m

$527

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 12/3

6:20 am-11:31 am

1 stop4h 11m

Winnipeg

Sun 12/6

9:35 pm-5:06 pm

2 stops20h 31m

$551

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 12/12

9:59 am-11:31 am

1 stop24h 32m

Winnipeg

Sun 12/13

9:35 pm-5:06 pm

2 stops20h 31m

$572

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 1/19

2:15 pm-3:09 pm

2 stops23h 54m

Winnipeg

Wed 2/3

1:45 pm-12:53 pm

2 stops24h 08m

$746

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 1/20

6:17 pm-1:24 am

1 stop6h 07m

Winnipeg

Sat 1/23

8:15 am-3:38 pm

1 stop8h 23m

$764

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 1/20

6:17 pm-1:24 am

1 stop6h 07m

Winnipeg

Sat 1/23

12:05 pm-5:43 pm

1 stop6h 38m

$764

Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 12/11

9:35 am-1:23 pm

Nonstop2h 48m

Winnipeg

Sun 12/13

3:15 pm-5:00 pm

Nonstop2h 45m

$866

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 Saturday when prices can be found for as low as $755. 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 $1,150.

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 $844. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $920 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 Airport to Winnipeg flights?

There is only 1 cabin class available to choose from on Chicago O'Hare Intl Airport 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 47% 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 November 2026, prices for Chicago O'Hare Intl Airport to Winnipeg flights are approximately 52% 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	$177
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 $177. The best round-trip flight deal from Chicago O'Hare Intl Airport to Winnipeg found on momondo in the last 72 hours is $385.

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?
There are 3 operators available for flights from Chicago O'Hare Intl Airport to Winnipeg Airport as of November 2026.
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?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 79.41% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 5.88%, Boeing 777-300ER with 5.88%, and Boeing 777-300 with 5.88%.
What is the most popular airline from Chicago O'Hare Intl Airport to Winnipeg?
momondo data reveals that the most frequently booked airline on the route from Chicago O'Hare Intl Airport to Winnipeg is United Airlines, representing 48% of all bookings. The subsequent popular airlines are WestJet at 29% and Air Canada at 23%.

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
WestJet	PriceFrom $208	Free Cancellation	Rating 7.2 3,436 reviews	Search WestJet flights
United Airlines	PriceFrom $291	Free Cancellation	Rating 7.3 10,472 reviews	Search United Airlines flights
Air Canada	PriceFrom $322	Free Cancellation	Rating 7.1 11,874 reviews	Search Air Canada 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 $291 round-trip, up to an average price of $865. Our users have rated United Airlines at 7.3/10.
Air Canada Flights From Chicago O'Hare Intl Airport to Winnipeg
Across 11,874 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 $322 to $780. Price data is based on momondo searches in the last 72 hours.

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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.