What is the cheapest airline that flies from Chicago to Winnipeg?

Porter Airlines is the most popular carrier operating from Chicago to Winnipeg

How many flights depart from Chicago to Winnipeg on average per day?

The number of flights available between Chicago and Winnipeg is 2 per day as of October 2026. The most frequent departure time is 10:00AM, with 60% of daily flights leaving at noon.

What airlines fly to Winnipeg?

United Airlines, WestJet and Air Canada are the top three most popular airlines that fly to Winnipeg from Chicago according to our data. United Airlines is the first choice among our users, with 55% 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.

How many flights depart from Chicago to Winnipeg on average per week?

15 flights are operational weekly from Chicago to Winnipeg as of October 2026. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.

When did momondo last update prices for flights from Chicago to Winnipeg Airport?

Prices for flights from Chicago to Winnipeg Airport refresh daily.

How many operators does momondo search for flights from Chicago to Winnipeg Airport?

As of October 2026, there are 3 operators available to choose from for flights from Chicago to Winnipeg Airport.

How old do you have to be to fly from Chicago 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 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.

$196 Cheap Flights from Chicago to Winnipeg in 2026/27

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Find the cheapest flights from Chicago to Winnipeg

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Cheap round-trip flights

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6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

7:55 pm - 11:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

16h 40m1 stop Toronto Pearson Intl

$376Multiple Airlines

Thu, Dec 3 - Sun, Dec 6

6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

7:55 pm - 11:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

16h 40m1 stop Toronto Pearson Intl

$386Multiple Airlines

Thu, Dec 3 - Sun, Dec 6

10:05 am - 7:10 pmORD Chicago O'Hare Intl-YWG Winnipeg

8h 05m1 stop Toronto Pearson Intl

11:00 am - 7:58 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 58m1 stop Toronto Pearson Intl

$440Multiple Airlines

Fri, Dec 4 - Sun, Dec 6

4:30 pm - 12:44 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 14m1 stop Toronto Pearson Intl

9:15 am - 7:58 pmYWG Winnipeg-ORD Chicago O'Hare Intl

11h 43m1 stop Toronto Pearson Intl

$649Air Canada

Wed, Nov 11 - Thu, Nov 19

7:02 am - 3:09 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 07m1 stop Toronto Pearson Intl

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

7h 58m1 stop Toronto Pearson Intl

$703Air Canada

Thu, Dec 10 - Thu, Dec 17

7:10 am - 1:48 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 38m1 stop Toronto Pearson Intl

5:15 am - 12:55 pmYWG Winnipeg-ORD Chicago O'Hare Intl

7h 40m1 stop Toronto Pearson Intl

$730Air Canada

Fri, Apr 2 - Tue, Apr 6

6:20 am - 11:54 amORD Chicago O'Hare Intl-YWG Winnipeg

4h 34m1 stop Minneapolis St Paul

9:35 pm - 12:24 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 49m2 stops Calgary Atlanta Hartsfield-Jackson

$996WestJet

Sat, Nov 21 - Tue, Dec 1

6:20 am - 11:54 amORD Chicago O'Hare Intl-YWG Winnipeg

4h 34m1 stop Minneapolis St Paul

6:00 am - 6:26 pmYWG Winnipeg-ORD Chicago O'Hare Intl

13h 26m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$1,004WestJet

Sat, Nov 21 - Thu, Dec 3

3:50 pm - 7:41 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mnonstop

7:00 am - 9:31 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mnonstop

$1,016United Airlines

Sat, Mar 13 - Fri, Mar 19

3:50 pm - 6:41 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mnonstop

7:00 am - 9:31 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mnonstop

$1,016United Airlines

Tue, Mar 16 - Sat, Mar 20

Cheap last minute flights

Enter your travel dates to find the best prices.

6:10 am - 7:45 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 35m1 stop Cancun

9:05 pm - 3:37 pmYWG Winnipeg-ORD Chicago O'Hare Intl

19h 32m2 stops Toronto Pearson Intl Fort Lauderdale

$874Multiple Airlines

Mon, Nov 2 - Sun, Nov 8

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

12h 45m1 stop Cancun

8:55 pm - 2:36 pmYWG Winnipeg-ORD Chicago O'Hare Intl

18h 41m2 stops Vancouver Intl Minneapolis St Paul

$951Multiple Airlines

Sun, Nov 1 - Sat, Nov 7

6:10 am - 1:30 amORD Chicago O'Hare Intl-YWG Winnipeg

18h 20m1 stop Cancun

9:05 pm - 11:34 amYWG Winnipeg-ORD Chicago O'Hare Intl

15h 29m1 stop Toronto Pearson Intl

$959Multiple Airlines

Mon, Nov 2 - Sun, Nov 8

6:10 am - 1:30 amORD Chicago O'Hare Intl-YWG Winnipeg

18h 20m1 stop Cancun

8:00 pm - 3:37 pmYWG Winnipeg-ORD Chicago O'Hare Intl

20h 37m3 stops Toronto Pearson Intl Ottawa Fort Lauderdale

$1,002Multiple Airlines

Mon, Nov 2 - Sun, Nov 8

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

$1,138Air Canada

Sun, Nov 1 - Sat, Nov 7

1:30 pm - 9:57 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 27m1 stop Denver Intl

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

2h 35mnonstop

$1,148Air Canada

Sun, Nov 1 - Sat, Nov 7

2:30 pm - 9:57 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Denver Intl

9:40 am - 6:38 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 58m1 stop Denver Intl

$1,163Air Canada

Sun, Nov 1 - Sat, Nov 7

12:27 pm - 12:48 pmMDW Chicago Midway-YWG Winnipeg

23h 21m1 stop Minneapolis St Paul

8:55 pm - 4:47 pmYWG Winnipeg-MDW Chicago Midway

20h 52m2 stops Vancouver Intl Minneapolis St Paul

$1,213WestJet

Sun, Nov 1 - Sat, Nov 7

6:44 pm - 1:44 amMDW Chicago Midway-YWG Winnipeg

30h 00m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

8:55 pm - 4:47 pmYWG Winnipeg-MDW Chicago Midway

20h 52m2 stops Vancouver Intl Minneapolis St Paul

$1,238WestJet

Sun, Nov 1 - Sat, Nov 7

10:12 am - 1:10 amMDW Chicago Midway-YWG Winnipeg

14h 58m2 stops Minneapolis St Paul Calgary

9:35 pm - 10:43 amYWG Winnipeg-MDW Chicago Midway

14h 08m2 stops Calgary Atlanta Hartsfield-Jackson

$1,582WestJet

Thu, Oct 29 - Sun, Nov 1

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WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

Nov 11

MDW10:34 amChicago Midway

5h 21m

1 stop

YWG4:55 pmWinnipeg

Nov 19

YWG6:00 amWinnipeg

13h 04m

2 stops

MDW6:04 pmChicago Midway

$921

WestJet

Nov 13

MDW5:29 pmChicago Midway

17h 25m

1 stop

YWG11:54 amWinnipeg

Nov 15

YWG6:35 amWinnipeg

6h 15m

1 stop

MDW11:50 amChicago Midway

$925

WestJet

Nov 11

MDW9:30 amChicago Midway

10h 20m

2 stops

YWG8:50 pmWinnipeg

Nov 19

YWG6:00 amWinnipeg

13h 04m

2 stops

MDW6:04 pmChicago Midway

$945

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

Feb 27

ORD6:20 pmChicago O'Hare Intl

16h 25m

1 stop

YWG11:45 amWinnipeg

Mar 9

YWG7:00 amWinnipeg

11h 40m

1 stop

ORD5:40 pmChicago O'Hare Intl

$475

Porter Airlines

Feb 27

ORD6:20 pmChicago O'Hare Intl

16h 25m

1 stop

YWG11:45 amWinnipeg

Mar 9

YWG11:40 amWinnipeg

25h 00m

2 stops

ORD11:40 amChicago O'Hare Intl

$484

Porter Airlines

Mar 6

ORD12:20 pmChicago O'Hare Intl

29h 50m

2 stops

YWG7:10 pmWinnipeg

Mar 13

YWG7:00 amWinnipeg

7h 02m

1 stop

ORD1:02 pmChicago O'Hare Intl

$583

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 12/3

6:20 pm-10:15 am

1 stop14h 55m

Winnipeg

Sun 12/6

7:55 pm-11:35 am

1 stop16h 40m

$376

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 12/3

6:20 pm-10:15 am

1 stop14h 55m

Winnipeg

Sun 12/6

7:55 pm-11:35 am

1 stop16h 40m

$386

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 12/4

10:05 am-7:10 pm

1 stop8h 05m

Winnipeg

Sun 12/6

11:00 am-7:58 pm

1 stop9h 58m

$440

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/11

4:30 pm-12:44 am

1 stop7h 14m

Winnipeg

Thu 11/19

9:15 am-7:58 pm

1 stop11h 43m

$649

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 12/10

7:02 am-3:09 pm

1 stop7h 07m

Winnipeg

Thu 12/17

6:15 am-1:13 pm

1 stop7h 58m

$703

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 4/2

7:10 am-1:48 pm

1 stop6h 38m

Winnipeg

Tue 4/6

5:15 am-12:55 pm

1 stop7h 40m

$730

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 11/21

6:20 am-11:54 am

1 stop4h 34m

Winnipeg

Tue 12/1

9:35 pm-12:24 pm

2 stops15h 49m

$996

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 11/21

6:20 am-11:54 am

1 stop4h 34m

Winnipeg

Thu 12/3

6:00 am-6:26 pm

2 stops13h 26m

$1,004

Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 3/13

3:50 pm-7:41 pm

Nonstop2h 51m

Winnipeg

Fri 3/19

7:00 am-9:31 am

Nonstop2h 31m

$1,016

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 3/16

3:50 pm-6:41 pm

Nonstop2h 51m

Winnipeg

Sat 3/20

7:00 am-9:31 am

Nonstop2h 31m

$1,016

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 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, September is the cheapest month to fly from Chicago to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $512. If you’re not able to fly to Winnipeg in September, then March is your next best option. Flight prices from Chicago to Winnipeg during March average around $528.

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 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 $887 on average. Flights to Winnipeg from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Winnipeg flight route?

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

What cabin class options are available on Chicago to Winnipeg flights?

There is only 1 cabin class available to choose from on Chicago 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 to Winnipeg flights?

You could potentially save up to 61% on your flight if you consider stops on a Chicago to Winnipeg flight.

How have Chicago to Winnipeg flight prices changed over time?

As of October 2026, prices for Chicago to Winnipeg flights are approximately 30% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Winnipeg

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Winnipeg according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Winnipeg (CHI to YWG) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Winnipeg

Best Price Found	$196
Fastest flight time	2h 24m
Direct flights	Every day
Airports in Winnipeg	1 airport

The best one-way flight to Winnipeg from Chicago in the past 72 hours is $196. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $376.

The fastest flight from Chicago to Winnipeg takes 2h 24m

Direct flights go from Chicago to Winnipeg every day.

There is 1 airport in Winnipeg. From Chicago there are direct flights to Winnipeg (YWG).

Search flight deals

Frequently asked questions about flying from Chicago to Winnipeg

How far is Chicago to Winnipeg by plane?
A flight from Chicago to Winnipeg will travel around 716.4 mi. Flights usually cover this in 2h 24m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport refresh daily.
How many operators does momondo search for flights from Chicago to Winnipeg Airport?
As of October 2026, there are 3 operators available to choose from for flights from Chicago to Winnipeg Airport.
How old do you have to be to fly from Chicago 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 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 to Winnipeg?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Winnipeg is Embraer 175 (Enhanced Winglets) (78.12% of total bookings). The next most popular plane models are Boeing 787-10 Dreamliner (6.25%), Boeing 777-300ER (6.25%), and Boeing 777-300 (6.25%).
What is the most popular airline from Chicago to Winnipeg?
momondo data reveals that the most frequently booked airline on the route from Chicago to Winnipeg is United Airlines, representing 51% of all bookings. The subsequent popular airline is Air Canada at 49%.

Best airlines flying from Chicago to Winnipeg

Compare and see reviews for airlines that fly from Chicago to Winnipeg with momondo

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom $208	Free Cancellation	Rating 7.2 3,444 reviews	Search WestJet flights
United Airlines	PriceFrom $291	Free Cancellation	Rating 7.3 10,444 reviews	Search United Airlines flights
Air Canada	PriceFrom $322	Free Cancellation	Rating 7.1 11,820 reviews	Search Air Canada flights

United Airlines Flights From Chicago to Winnipeg
United Airlines flies from Chicago to Winnipeg around 5 times per week, with 10,444 momondo users rating the airline 7.3/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $291 (round-trip), much lower than the average airfare cost of $762 for United Airlines flights on this route.
Air Canada Flights From Chicago to Winnipeg
The best Air Canada deal for Chicago to Winnipeg flight tickets found on momondo in the last 72 hours was $322, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at $780 round-trip. Air Canada operates 5 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 11,820 Air Canada reviews by users on momondo have scored the airline at 7.1/10.

Selkirk

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Why use momondo?

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

Finding the right flight to Winnipeg from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Winnipeg from Chicago with this policy.

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

Once you have performed a search for Chicago to Winnipeg flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Winnipeg now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Winnipeg and let you know when they change.