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

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

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

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 November 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 November 2025, there are 2 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.

$87 Cheap Flights from Chicago to Winnipeg in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and Winnipeg?

Prices are currently low for flights on this route. Typical prices usually range from $448 to $670. The lowest price recently found on this route was $224.

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5:01 pm - 3:07 pmMDW-YWG

22h 06m1 stop

9:00 pm - 11:45 amYWG-MDW

14h 45m2 stops

$224Multiple Airlines

Find Deal

Thu, Jan 22 - Thu, Jan 29

5:01 pm - 3:07 pmMDW-YWG

22h 06m1 stop

9:00 pm - 11:45 amYWG-MDW

14h 45m2 stops

$225Multiple Airlines

Find Deal

Thu, Jan 22 - Thu, Jan 29

5:40 am - 3:09 pmORD-YWG

9h 29m1 stop

6:15 am - 11:35 pmYWG-ORD

17h 20m2 stops

$227Multiple Airlines

Find Deal

Sun, Feb 8 - Thu, Feb 19

8:42 pm - 6:06 pmMDW-YWG

21h 24m2 stops

7:30 am - 7:42 pmYWG-MDW

12h 12m1 stop

$281Multiple Airlines

Find Deal

Mon, Dec 8 - Fri, Dec 12

5:40 am - 12:41 amORD-YWG

19h 01m2 stops

9:00 pm - 1:35 pmYWG-ORD

16h 35m1 stop

$282Multiple Airlines

Find Deal

Thu, Jan 22 - Thu, Jan 29

6:11 am - 3:07 pmORD-YWG

8h 56m1 stop

9:00 pm - 2:31 pmYWG-ORD

17h 31m2 stops

$285Multiple Airlines

Find Deal

Fri, Dec 5 - Tue, Dec 9

2:20 pm - 10:41 pmORD-YWG

8h 21m1 stop

6:55 pm - 1:35 pmYWG-ORD

18h 40m1 stop

$303WestJet

Find Deal

Fri, Jan 23 - Sun, Jan 25

8:27 pm - 3:07 pmORD-YWG

18h 40m2 stops

9:00 pm - 1:35 pmYWG-ORD

16h 35m1 stop

$304Multiple Airlines

Find Deal

Thu, Jan 22 - Thu, Jan 29

8:22 pm - 7:35 pmORD-YWG

23h 13m2 stops

9:00 pm - 2:19 pmYWG-ORD

17h 19m3 stops

$356Multiple Airlines

Find Deal

Thu, Jan 22 - Thu, Jan 29

9:50 am - 11:03 amMDW-YWG

25h 13m1 stop

5:21 pm - 1:09 pmYWG-MDW

19h 48m1 stop

$539WestJet

Find Deal

Tue, Jan 6 - Tue, Jan 13

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

Jan 23

ORD2:20 pmChicago O'Hare Intl

8h 21m

1 stop

YWG10:41 pmWinnipeg

Jan 25

YWG6:55 pmWinnipeg

18h 40m

1 stop

ORD1:35 pmChicago O'Hare Intl

$303

Find similar

WestJet

Jan 23

ORD2:20 pmChicago O'Hare Intl

8h 21m

1 stop

YWG10:41 pmWinnipeg

Jan 25

YWG5:00 amWinnipeg

16h 05m

2 stops

ORD9:05 pmChicago O'Hare Intl

$390

Find similar

WestJet

Jan 22

ORD6:15 amChicago O'Hare Intl

4h 48m

1 stop

YWG11:03 amWinnipeg

Jan 29

YWG4:10 pmWinnipeg

21h 25m

1 stop

ORD1:35 pmChicago O'Hare Intl

$441

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Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets

Delta

Jan 8

MDW9:50 amChicago Midway

13h 48m

1 stop

YWG11:38 pmWinnipeg

Jan 11

YWG5:21 pmWinnipeg

25h 11m

1 stop

MDW6:32 pmChicago Midway

$640

Find similar

Delta

Jan 22

MDW9:50 amChicago Midway

6h 39m

1 stop

YWG4:29 pmWinnipeg

Jan 29

YWG6:40 amWinnipeg

6h 29m

1 stop

MDW1:09 pmChicago Midway

$755

Find similar

Delta

Dec 25

MDW5:59 pmChicago Midway

5h 45m

1 stop

YWG11:44 pmWinnipeg

Dec 28

YWG6:40 amWinnipeg

4h 26m

1 stop

MDW11:06 amChicago Midway

$1,088

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 1/22

5:01 pm-3:07 pm

1 stop22h 06m

Winnipeg

Thu 1/29

9:00 pm-11:45 am

2 stops14h 45m

$224

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 1/22

5:01 pm-3:07 pm

1 stop22h 06m

Winnipeg

Thu 1/29

9:00 pm-11:45 am

2 stops14h 45m

$225

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 2/8

5:40 am-3:09 pm

1 stop9h 29m

Winnipeg

Thu 2/19

6:15 am-11:35 pm

2 stops17h 20m

$227

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 12/8

8:42 pm-6:06 pm

2 stops21h 24m

Winnipeg

Fri 12/12

7:30 am-7:42 pm

1 stop12h 12m

$281

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/22

5:40 am-12:41 am

2 stops19h 01m

Winnipeg

Thu 1/29

9:00 pm-1:35 pm

1 stop16h 35m

$282

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 12/5

6:11 am-3:07 pm

1 stop8h 56m

Winnipeg

Tue 12/9

9:00 pm-2:31 pm

2 stops17h 31m

$285

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/23

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Sun 1/25

6:55 pm-1:35 pm

1 stop18h 40m

$303

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/22

8:27 pm-3:07 pm

2 stops18h 40m

Winnipeg

Thu 1/29

9:00 pm-1:35 pm

1 stop16h 35m

$304

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/22

8:22 pm-7:35 pm

2 stops23h 13m

Winnipeg

Thu 1/29

9:00 pm-2:19 pm

3 stops17h 19m

$356

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 1/6

9:50 am-11:03 am

1 stop25h 13m

Winnipeg

Tue 1/13

5:21 pm-1:09 pm

1 stop19h 48m

$539

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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 typical price of a round-trip flight between Chicago and Winnipeg?

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 Saturday 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 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 $632 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	$1,004
Fastest flight time	2h 35m
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 $1,004

The fastest flight from Chicago to Winnipeg takes 2h 35m

Direct flights go from Chicago to Winnipeg every day.

There is 1 airport near Winnipeg: 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 4h 48m, 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 November 2025, there are 2 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) (67.19% of total bookings). The next most popular plane models are Boeing 777-300ER (7.81%), Boeing 737 MAX 8 (4.69%), and Airbus A319 (3.12%).
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 73% of all bookings. The subsequent popular airline is Air Canada at 27%.

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
Air Canada	PriceFrom $230	Free Cancellation	Rating 7.1 10,464 reviews		Search Air Canada flights
United Airlines	PriceFrom $415	Free Cancellation	Rating 7.4 9,035 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 9,035 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 $614 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. 10,464 Air Canada reviews by users on momondo have scored the airline at 7.1/10.

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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.

An easier way to manage your Winnipeg trip

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Cheap flights from Chicago to Winnipeg from $87

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 to Winnipeg departing on 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets

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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

What is the typical price of a round-trip flight between Chicago and Winnipeg?

What is the cheapest month to fly to Winnipeg?

What is the cheapest day to depart on your flight to Winnipeg?

What is the cheapest time of day to depart on your flight to Winnipeg?

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?

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

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 November 2025. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

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

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

When to book flights from Chicago to Winnipeg

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

Fastest flight time

Direct flights

Airports in Winnipeg

How far is Chicago to Winnipeg by plane?

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

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

How old do you have to be to fly from Chicago to Winnipeg Airport?

What documentation or ID do you need to fly to Winnipeg Airport?

What is the most popular plane model from Chicago to Winnipeg?

What is the most popular airline from Chicago to Winnipeg?

Best airlines flying from Chicago to Winnipeg

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

United Airlines Flights From Chicago to Winnipeg

Air Canada Flights From Chicago to Winnipeg

Traveling to a place near Winnipeg?

Why use momondo?

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

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

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

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

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Canada

Airports servicing Manitoba