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 63% 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 day?

The number of flights available between Chicago and Winnipeg is 3 per day as of April 2026. 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 April 2026. 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?

WestJet, Air Transat, and Porter 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 April 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.

$149 Cheap Flights from Chicago to Winnipeg in 2026

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 $777 to $480. The lowest price recently found on this route was $251.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Winnipeg

Round-trip

One-way

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

6:00 am - 4:40 pm

YWG

ORD

10h 40m

1 stop

$251WestJet

Tue, May 26 - Fri, May 29

5:30 pm - 12:15 pm

ORD

YWG

18h 45m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$255WestJet

Sat, May 23 - Mon, May 25

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$256WestJet

Tue, May 26 - Tue, Jun 2

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$259WestJet

Fri, May 29 - Mon, Jun 1

5:30 pm - 11:10 am

ORD

YWG

17h 40m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$279WestJet

Tue, May 26 - Tue, Jun 2

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

9:05 pm - 7:29 pm

YWG

ORD

22h 24m

2 stops

$285Multiple Airlines

Fri, May 29 - Mon, Jun 1

5:30 pm - 12:15 pm

ORD

YWG

18h 45m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$291WestJet

Wed, May 27 - Tue, Jun 2

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

9:05 pm - 7:55 am

YWG

ORD

34h 50m

2 stops

$299Multiple Airlines

Tue, May 26 - Tue, Jun 2

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

6:00 am - 4:40 pm

YWG

ORD

10h 40m

1 stop

$308WestJet

Mon, May 25 - Fri, May 29

10:30 am - 7:49 pm

MDW

YWG

9h 19m

1 stop

11:40 am - 9:40 am

YWG

MDW

22h 00m

2 stops

$500Porter Airlines

Thu, May 28 - Sun, May 31

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WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

May 26

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

May 29

YWG6:00 amWinnipeg

10h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$251

WestJet

May 23

ORD5:30 pmChicago O'Hare Intl

18h 45m

1 stop

YWG12:15 pmWinnipeg

May 25

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$255

WestJet

May 26

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Jun 2

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$256

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

Jun 2

MDW10:15 amChicago Midway

9h 34m

1 stop

YWG7:49 pmWinnipeg

Jun 4

YWG11:40 amWinnipeg

22h 00m

2 stops

MDW9:40 amChicago Midway

$475

Porter Airlines

May 28

MDW10:30 amChicago Midway

9h 19m

1 stop

YWG7:49 pmWinnipeg

May 31

YWG11:40 amWinnipeg

22h 00m

2 stops

MDW9:40 amChicago Midway

$500

Porter Airlines

Jun 11

MDW10:15 amChicago Midway

7h 43m

2 stops

YWG5:58 pmWinnipeg

Jun 18

YWG4:15 pmWinnipeg

17h 25m

2 stops

MDW9:40 amChicago Midway

$533

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/26

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 5/29

6:00 am-4:40 pm

1 stop10h 40m

$251

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/23

5:30 pm-12:15 pm

1 stop18h 45m

Winnipeg

Mon 5/25

7:00 am-4:40 pm

1 stop9h 40m

$255

Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/26

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Tue 6/2

7:00 am-4:40 pm

1 stop9h 40m

$256

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Mon 6/1

7:00 am-4:40 pm

1 stop9h 40m

$259

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/26

5:30 pm-11:10 am

1 stop17h 40m

Winnipeg

Tue 6/2

7:00 am-4:40 pm

1 stop9h 40m

$279

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Mon 6/1

9:05 pm-7:29 pm

2 stops22h 24m

$285

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 5/27

5:30 pm-12:15 pm

1 stop18h 45m

Winnipeg

Tue 6/2

7:00 am-4:40 pm

1 stop9h 40m

$291

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/26

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Tue 6/2

9:05 pm-7:55 am

2 stops34h 50m

$299

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 5/29

6:00 am-4:40 pm

1 stop10h 40m

$308

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/28

10:30 am-7:49 pm

1 stop9h 19m

Winnipeg

Sun 5/31

11:40 am-9:40 am

2 stops22h 00m

$500

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, February 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 $62. If you’re not able to fly to Winnipeg in February, then October is your next best option. Flight prices from Chicago to Winnipeg during October average around $81.

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 Tuesday when prices can be found for as low as $584. 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 $1,074.

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 $552. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $758 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

Can stopping save me money on Chicago to Winnipeg flights?

You could potentially save up to 7% 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	$624
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 $624. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $755.

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 April 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) (57.89% of total bookings). The next most popular plane models are Boeing 777-300ER (8.77%), Boeing 787-10 Dreamliner (7.02%), and Boeing 777-300 (7.02%).
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 100% of all bookings.

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 3,328 reviews	Search WestJet flights
Air Canada	PriceFrom $226	Free Cancellation	Rating 7.1 10,979 reviews	Search Air Canada flights
United Airlines	PriceFrom $263	Free Cancellation	Rating 7.4 9,680 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 9,680 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $263 (round-trip), much lower than the average airfare cost of $661 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 $509 round-trip. Air Canada operates 7 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 10,979 Air Canada reviews by users on momondo have scored the airline at 7.1/10.

Selkirk

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Morden

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.