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

49 flights are operational weekly from Chicago to Winnipeg as of October 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 7 per day as of October 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, Air Canada, and Delta 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 October 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.

$97 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 $301 to $662. The lowest price recently found on this route was $231.

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.

5:11 am - 3:07 pmORD-YWG

9h 56m1 stop

6:15 am - 1:35 pmYWG-ORD

7h 20m1 stop

$231Multiple Airlines

Find Deal

Fri, Nov 7 - Mon, Nov 10

6:15 am - 3:07 pmMDW-YWG

8h 52m1 stop

9:00 pm - 12:41 pmYWG-MDW

15h 41m2 stops

$247Multiple Airlines

Find Deal

Sun, Nov 9 - Tue, Nov 11

5:11 am - 12:41 amORD-YWG

19h 30m2 stops

6:15 am - 1:35 pmYWG-ORD

7h 20m1 stop

$251Multiple Airlines

Find Deal

Fri, Nov 7 - Mon, Nov 10

5:01 am - 3:07 pmORD-YWG

10h 06m1 stop

9:00 pm - 11:14 amYWG-ORD

14h 14m2 stops

$257Multiple Airlines

Find Deal

Sun, Nov 9 - Tue, Nov 11

2:20 pm - 10:40 pmORD-YWG

8h 20m1 stop

12:40 pm - 4:48 pmYWG-ORD

4h 08m1 stop

$335WestJet

Find Deal

Fri, Apr 3 - Tue, Apr 7

2:20 pm - 10:40 pmORD-YWG

8h 20m1 stop

5:00 am - 6:46 pmYWG-ORD

13h 46m2 stops

$346WestJet

Find Deal

Fri, Apr 3 - Tue, Apr 7

3:40 pm - 1:09 amORD-YWG

9h 29m1 stop

8:00 am - 5:10 pmYWG-ORD

9h 10m1 stop

$547Air Canada

Find Deal

Fri, Oct 31 - Wed, Nov 5

8:06 am - 11:35 pmORD-YWG

15h 29m1 stop

6:00 am - 2:14 pmYWG-ORD

8h 14m1 stop

$555American Airlines

Find Deal

Fri, Dec 19 - Sat, Jan 31

9:20 am - 4:50 pmMDW-YWG

7h 30m1 stop

12:20 pm - 5:43 pmYWG-MDW

5h 23m1 stop

$685Delta

Find Deal

Fri, Oct 31 - Wed, Nov 5

5:59 pm - 11:44 pmMDW-YWG

5h 45m1 stop

6:40 am - 1:08 pmYWG-MDW

6h 28m1 stop

$852Delta

Find Deal

Mon, Dec 22 - Wed, Jan 28

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

Apr 3

ORD2:20 pmChicago O'Hare Intl

8h 20m

1 stop

YWG10:40 pmWinnipeg

Apr 7

YWG12:40 pmWinnipeg

4h 08m

1 stop

ORD4:48 pmChicago O'Hare Intl

$335

Find similar

WestJet

Apr 3

ORD2:20 pmChicago O'Hare Intl

8h 20m

1 stop

YWG10:40 pmWinnipeg

Apr 7

YWG5:00 amWinnipeg

13h 46m

2 stops

ORD6:46 pmChicago O'Hare Intl

$346

Find similar

WestJet

Oct 16

ORD5:30 pmChicago O'Hare Intl

27h 55m

2 stops

YWG9:25 pmWinnipeg

Oct 24

YWG6:30 amWinnipeg

10h 13m

2 stops

ORD4:43 pmChicago O'Hare Intl

$351

Find similar

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets

Air Canada

Oct 31

ORD3:40 pmChicago O'Hare Intl

9h 29m

1 stop

YWG1:09 amWinnipeg

Nov 5

YWG8:00 amWinnipeg

9h 10m

1 stop

ORD5:10 pmChicago O'Hare Intl

$547

Find similar

Air Canada

Oct 19

ORD7:54 pmChicago O'Hare Intl

2h 39m

YWG10:33 pmWinnipeg

Oct 29

YWG8:00 amWinnipeg

9h 10m

1 stop

ORD5:10 pmChicago O'Hare Intl

$680

Find similar

Air Canada

Oct 19

ORD7:54 pmChicago O'Hare Intl

2h 39m

YWG10:33 pmWinnipeg

Oct 29

YWG8:00 amWinnipeg

9h 10m

1 stop

ORD5:10 pmChicago O'Hare Intl

$681

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/7

5:11 am-3:07 pm

1 stop9h 56m

Winnipeg

Mon 11/10

6:15 am-1:35 pm

1 stop7h 20m

$231

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 11/9

6:15 am-3:07 pm

1 stop8h 52m

Winnipeg

Tue 11/11

9:00 pm-12:41 pm

2 stops15h 41m

$247

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/7

5:11 am-12:41 am

2 stops19h 30m

Winnipeg

Mon 11/10

6:15 am-1:35 pm

1 stop7h 20m

$251

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 11/9

5:01 am-3:07 pm

1 stop10h 06m

Winnipeg

Tue 11/11

9:00 pm-11:14 am

2 stops14h 14m

$257

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 4/3

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Tue 4/7

12:40 pm-4:48 pm

1 stop4h 08m

$335

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 4/3

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Tue 4/7

5:00 am-6:46 pm

2 stops13h 46m

$346

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/31

3:40 pm-1:09 am

1 stop9h 29m

Winnipeg

Wed 11/5

8:00 am-5:10 pm

1 stop9h 10m

$547

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 12/19

8:06 am-11:35 pm

1 stop15h 29m

Winnipeg

Sat 1/31

6:00 am-2:14 pm

1 stop8h 14m

$555

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 10/31

9:20 am-4:50 pm

1 stop7h 30m

Winnipeg

Wed 11/5

12:20 pm-5:43 pm

1 stop5h 23m

$685

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 12/22

5:59 pm-11:44 pm

1 stop5h 45m

Winnipeg

Wed 1/28

6:40 am-1:08 pm

1 stop6h 28m

$852

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 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 $675.

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 $639 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?

You could potentially save up to 62% 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	$490
Fastest flight time	2h 30m
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 $490

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

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 5h 07m, 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 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) (76.70% of total bookings). The next most popular plane models are Boeing 777-300ER (7.77%), Boeing 737 MAX 8 (2.91%), and Airbus A319 (1.94%).
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 71% of all bookings. The subsequent popular airline is Air Canada at 29%.

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 10,000 reviews		Search Air Canada flights
United Airlines	PriceFrom $415	Free Cancellation	Rating 7.4 8,953 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Winnipeg
United Airlines flies from Chicago to Winnipeg around 14 times per week, with 8,953 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 $618 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 $585 round-trip. Air Canada operates 14 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 10,000 Air Canada reviews by users on momondo have scored the airline at 7.1/10.

Scanterbury

Selkirk

Morden

Portage la Prairie

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.