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

Porter Airlines and WestJet are the most popular carriers operating from Chicago to Winnipeg

What airlines fly to Winnipeg?

United Airlines, Air Canada and WestJet 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 69% 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?

21 flights are operational weekly from Chicago to Winnipeg as of December 2025. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

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

The number of flights available between Chicago and Winnipeg is 3 per day as of December 2025. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

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 December 2025, 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.

$113 Cheap Flights from Chicago to Winnipeg in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Winnipeg

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:51 pm - 12:43 am

ORD

YWG

29h 52m1 stop

4:10 pm - 10:43 am

YWG

ORD

18h 33m2 stops

$235Multiple Airlines

Sat, Jan 10 - Thu, Jan 15

8:10 am - 12:41 am

ORD

YWG

16h 31m2 stops

4:55 pm - 2:54 pm

YWG

ORD

21h 59m1 stop

$258Multiple Airlines

Wed, Feb 18 - Sun, Feb 22

8:10 am - 12:36 am

ORD

YWG

16h 26m1 stop

4:55 pm - 2:54 pm

YWG

ORD

21h 59m1 stop

$260Multiple Airlines

Wed, Feb 18 - Sun, Feb 22

5:50 am - 3:07 pm

ORD

YWG

9h 17m1 stop

4:10 pm - 7:36 pm

YWG

ORD

27h 26m2 stops

$266Multiple Airlines

Wed, Jan 7 - Wed, Jan 14

6:20 am - 3:07 pm

MDW

YWG

8h 47m1 stop

7:30 am - 10:19 pm

YWG

MDW

14h 49m1 stop

$269Multiple Airlines

Sun, Jan 25 - Sun, Feb 1

5:01 pm - 12:41 am

MDW

YWG

31h 40m2 stops

7:30 am - 10:19 pm

YWG

MDW

14h 49m1 stop

$280Multiple Airlines

Sun, Jan 25 - Sun, Feb 1

6:20 am - 3:07 pm

ORD

YWG

8h 47m1 stop

7:30 am - 10:44 pm

YWG

ORD

15h 14m1 stop

$284Multiple Airlines

Fri, Jan 16 - Sun, Jan 18

6:51 pm - 12:43 am

ORD

YWG

29h 52m1 stop

9:00 pm - 1:35 pm

YWG

ORD

16h 35m1 stop

$287Multiple Airlines

Sat, Jan 10 - Thu, Jan 15

5:30 pm - 11:40 am

ORD

YWG

18h 10m1 stop

8:30 am - 4:43 pm

YWG

ORD

8h 13m1 stop

$307WestJet

Fri, Jun 5 - Sun, Jun 7

5:30 pm - 11:40 am

ORD

YWG

18h 10m1 stop

8:30 am - 4:43 pm

YWG

ORD

8h 13m1 stop

$320WestJet

Mon, May 25 - Mon, Jun 1

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

Jun 5

ORD5:30 pmChicago O'Hare Intl

18h 10m

1 stop

YWG11:40 amWinnipeg

Jun 7

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$307

Find similar

WestJet

May 25

ORD5:30 pmChicago O'Hare Intl

18h 10m

1 stop

YWG11:40 amWinnipeg

Jun 1

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$320

Find similar

WestJet

May 25

ORD5:30 pmChicago O'Hare Intl

26h 45m

1 stop

YWG8:15 pmWinnipeg

Jun 1

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$325

Find similar

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

Apr 23

ORD8:00 amChicago O'Hare Intl

7h 30m

1 stop

YWG3:30 pmWinnipeg

Apr 28

YWG12:10 pmWinnipeg

7h 25m

1 stop

ORD7:35 pmChicago O'Hare Intl

$530

Find similar

Porter Airlines

Apr 23

ORD8:00 amChicago O'Hare Intl

7h 30m

1 stop

YWG3:30 pmWinnipeg

Apr 28

YWG12:10 pmWinnipeg

7h 25m

1 stop

ORD7:35 pmChicago O'Hare Intl

$541

Find similar

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

$561

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/10

6:51 pm-12:43 am

1 stop29h 52m

Winnipeg

Thu 1/15

4:10 pm-10:43 am

2 stops18h 33m

$235

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 2/18

8:10 am-12:41 am

2 stops16h 31m

Winnipeg

Sun 2/22

4:55 pm-2:54 pm

1 stop21h 59m

$258

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 2/18

8:10 am-12:36 am

1 stop16h 26m

Winnipeg

Sun 2/22

4:55 pm-2:54 pm

1 stop21h 59m

$260

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 1/7

5:50 am-3:07 pm

1 stop9h 17m

Winnipeg

Wed 1/14

4:10 pm-7:36 pm

2 stops27h 26m

$266

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 1/25

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

Sun 2/1

7:30 am-10:19 pm

1 stop14h 49m

$269

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 1/25

5:01 pm-12:41 am

2 stops31h 40m

Winnipeg

Sun 2/1

7:30 am-10:19 pm

1 stop14h 49m

$280

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/16

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

Sun 1/18

7:30 am-10:44 pm

1 stop15h 14m

$284

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/10

6:51 pm-12:43 am

1 stop29h 52m

Winnipeg

Thu 1/15

9:00 pm-1:35 pm

1 stop16h 35m

$287

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/5

5:30 pm-11:40 am

1 stop18h 10m

Winnipeg

Sun 6/7

8:30 am-4:43 pm

1 stop8h 13m

$307

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-11:40 am

1 stop18h 10m

Winnipeg

Mon 6/1

8:30 am-4:43 pm

1 stop8h 13m

$320

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, May 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 $271. If you’re not able to fly to Winnipeg in May, then January is your next best option. Flight prices from Chicago to Winnipeg during January average around $319.

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, Monday 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 $648.

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 at noon 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 are 2 cabin classes 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?

No. A direct flight is the cheapest option for a flight between Chicago to Winnipeg.

How have Chicago to Winnipeg flight prices changed over time?

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	$680
Fastest flight time	2h 24m
Direct flights	Every day
Airports in Winnipeg	1 airport

The best flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $680

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

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 December 2025, 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) (70.42% of total bookings). The next most popular plane models are Boeing 777-300ER (7.04%), Boeing 737 MAX 8 (4.23%), and Airbus A319 (2.82%).
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 78% of all bookings. The subsequent popular airline is Air Canada at 22%.

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 $156	Free Cancellation	Rating 7.2 3,195 reviews	Search WestJet flights
Air Canada	PriceFrom $230	Free Cancellation	Rating 7.1 10,516 reviews	Search Air Canada flights
United Airlines	PriceFrom $415	Free Cancellation	Rating 7.4 9,095 reviews	Search United Airlines flights

United Airlines Flights From Chicago to Winnipeg
United Airlines flies from Chicago to Winnipeg around 7 times per week, with 9,095 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $415 (round-trip), much lower than the average airfare cost of $645 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 $230, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at $552 round-trip. Air Canada operates 7 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 10,516 Air Canada reviews by users on momondo have scored the airline at 7.1/10.

Scanterbury

Selkirk

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.