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

40 flights are operational weekly from Chicago to Winnipeg as of August 2025. The most popular departure day for this route is Wed, with 18% 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 5 per day as of August 2025. The most frequent departure time is 7:00PM, with 57% of daily flights leaving in the evening.

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

WestJet, Delta, and United Airlines are the most popular carriers operating from Chicago to Winnipeg

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 August 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.

$53 Cheap Flights from Chicago to Winnipeg in 2025

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Find the cheapest flights from Chicago to Winnipeg

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:30 pm - 11:26 amORD-YWG

17h 56m2 stops

9:00 am - 5:21 pmYWG-ORD

8h 21m1 stop

$226

Find Deal

Mon, Sep 29 - Mon, Oct 6

5:30 pm - 11:10 pmORD-YWG

29h 40m1 stop

8:30 am - 4:43 pmYWG-ORD

8h 13m1 stop

$232WestJet

Find Deal

Fri, Oct 17 - Mon, Oct 20

5:30 pm - 9:30 pmORD-YWG

28h 00m1 stop

8:30 am - 4:43 pmYWG-ORD

8h 13m1 stop

$234WestJet

Find Deal

Thu, Oct 16 - Fri, Oct 24

5:30 pm - 11:26 amORD-YWG

17h 56m2 stops

8:30 am - 4:43 pmYWG-ORD

8h 13m1 stop

$242WestJet

Find Deal

Thu, Oct 16 - Fri, Oct 24

5:30 pm - 11:41 amORD-YWG

18h 11m1 stop

9:00 am - 5:21 pmYWG-ORD

8h 21m1 stop

$246

Find Deal

Mon, Sep 29 - Mon, Oct 6

5:30 pm - 8:15 pmORD-YWG

26h 45m1 stop

4:30 pm - 12:39 pmYWG-ORD

20h 09m1 stop

$250WestJet

Find Deal

Fri, Sep 12 - Fri, Sep 19

7:54 pm - 10:33 pmORD-YWG

2h 39mnonstop

7:00 am - 9:31 amYWG-ORD

2h 31mnonstop

$384United Airlines

Find Deal

Thu, Sep 11 - Sun, Sep 14

1:43 pm - 8:11 pmMDW-YWG

6h 28m1 stop

8:35 am - 1:03 pmYWG-MDW

4h 28m1 stop

$526Delta

Find Deal

Thu, Sep 11 - Sun, Sep 14

4:15 pm - 11:13 amMDW-YWG

18h 58m2 stops

4:25 pm - 10:05 amYWG-MDW

17h 40m2 stops

$622Porter Airlines

Find Deal

Fri, Oct 31 - Wed, Nov 5

7:15 pm - 11:27 pmMDW-YWG

4h 12m1 stop

8:35 am - 1:03 pmYWG-MDW

4h 28m1 stop

$638Delta

Find Deal

Sun, Sep 14 - Sun, Sep 21

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

Oct 17

ORD5:30 pmChicago O'Hare Intl

29h 40m

1 stop

YWG11:10 pmWinnipeg

Oct 20

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$232

Find similar

WestJet

Oct 16

ORD5:30 pmChicago O'Hare Intl

28h 00m

1 stop

YWG9:30 pmWinnipeg

Oct 24

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$234

Find similar

WestJet

Oct 16

ORD5:30 pmChicago O'Hare Intl

17h 56m

2 stops

YWG11:26 amWinnipeg

Oct 24

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$242

Find similar

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets

Delta

Sep 11

MDW1:43 pmChicago Midway

6h 28m

1 stop

YWG8:11 pmWinnipeg

Sep 14

YWG8:35 amWinnipeg

4h 28m

1 stop

MDW1:03 pmChicago Midway

$526

Find similar

Delta

Sep 14

MDW7:15 pmChicago Midway

4h 12m

1 stop

YWG11:27 pmWinnipeg

Sep 21

YWG8:35 amWinnipeg

4h 28m

1 stop

MDW1:03 pmChicago Midway

$638

Find similar

Delta

Sep 11

MDW9:35 amChicago Midway

10h 36m

2 stops

YWG8:11 pmWinnipeg

Sep 14

YWG8:35 amWinnipeg

4h 28m

1 stop

MDW1:03 pmChicago Midway

$648

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 9/29

5:30 pm-11:26 am

2 stops17h 56m

Winnipeg

Mon 10/6

9:00 am-5:21 pm

1 stop8h 21m

$226

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/17

5:30 pm-11:10 pm

1 stop29h 40m

Winnipeg

Mon 10/20

8:30 am-4:43 pm

1 stop8h 13m

$232

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/16

5:30 pm-9:30 pm

1 stop28h 00m

Winnipeg

Fri 10/24

8:30 am-4:43 pm

1 stop8h 13m

$234

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/16

5:30 pm-11:26 am

2 stops17h 56m

Winnipeg

Fri 10/24

8:30 am-4:43 pm

1 stop8h 13m

$242

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 9/29

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

Mon 10/6

9:00 am-5:21 pm

1 stop8h 21m

$246

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/12

5:30 pm-8:15 pm

1 stop26h 45m

Winnipeg

Fri 9/19

4:30 pm-12:39 pm

1 stop20h 09m

$250

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/11

7:54 pm-10:33 pm

Nonstop2h 39m

Winnipeg

Sun 9/14

7:00 am-9:31 am

Nonstop2h 31m

$384

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 9/11

1:43 pm-8:11 pm

1 stop6h 28m

Winnipeg

Sun 9/14

8:35 am-1:03 pm

1 stop4h 28m

$526

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 10/31

4:15 pm-11:13 am

2 stops18h 58m

Winnipeg

Wed 11/5

4:25 pm-10:05 am

2 stops17h 40m

$622

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 9/14

7:15 pm-11:27 pm

1 stop4h 12m

Winnipeg

Sun 9/21

8:35 am-1:03 pm

1 stop4h 28m

$638

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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 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 Friday when prices can be found for as low as $556. 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 $714.

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 $631 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 3 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?

You could potentially save up to 45% on your flight if you consider stops on a Chicago to Winnipeg flight.

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	$53
Fastest flight time	2h 30m
Direct flights	Tue, Wed, Thu, Fri, Sat and Sun
Airports in Winnipeg	1 airport

The best one-way flight to Winnipeg from Chicago in the past 72 hours is $53. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $226.

The fastest flight from Chicago to Winnipeg takes 2h 30m

Direct flights go from Chicago to Winnipeg on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Air Canada.

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 2h 39m, 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 August 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) (82.21% of total bookings). The next most popular plane models are Boeing 777-300ER (6.13%), Boeing 737 MAX 8 (1.84%), and Boeing 787-10 Dreamliner (1.23%).
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 70% of all bookings. The subsequent popular airline is Air Canada at 30%.

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 $226	Free Cancellation	Rating 7.1 9,966 reviews		Search Air Canada flights
United Airlines	PriceFrom $429	Free Cancellation	Rating 7.4 8,916 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 8,916 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $429 (round-trip), much lower than the average airfare cost of $627 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 $226, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at $542 round-trip. Air Canada operates 8 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 9,966 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

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.

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Cheap flights from Chicago to Winnipeg from $53

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 9/27. 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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Big names and deals

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Find the cheapest flights from Chicago to Winnipeg

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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 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 3 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?

You could potentially save up to 45% on your flight if you consider stops on a Chicago to Winnipeg flight.

How have Chicago to Winnipeg flight prices changed over time?

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

WestJet, Delta, and United Airlines 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 5 per day as of August 2025. The most frequent departure time is 7:00PM, with 57% of daily flights leaving in the evening.

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

40 flights are operational weekly from Chicago to Winnipeg as of August 2025. The most popular departure day for this route is Wed, with 18% 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