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

WestJet and Porter 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 7 per day as of June 2026. The most frequent departure time is 8:00PM, with 62% of daily flights leaving in the evening.

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

54 flights are operational weekly from Chicago to Winnipeg as of June 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

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 June 2026, 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.

$170 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 $1,010 to $817. The lowest price recently found on this route was $405.

Discover deals from 900+ travel sites with momondo.

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.

10:25 am - 8:40 am

MDW

YWG

22h 15m

1 stop

8:10 pm - 9:40 am

YWG

MDW

13h 30m

1 stop

$405Multiple Airlines

Thu, Jun 25 - Mon, Jun 29

5:30 pm - 11:10 am

ORD

YWG

17h 40m

1 stop

11:15 am - 9:35 pm

YWG

ORD

10h 20m

2 stops

$410Multiple Airlines

Fri, Sep 18 - Sun, Sep 20

10:25 am - 8:40 am

MDW

YWG

22h 15m

1 stop

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$418Multiple Airlines

Thu, Jun 25 - Wed, Jul 1

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

4:15 pm - 11:00 am

YWG

ORD

18h 45m

2 stops

$419Multiple Airlines

Sun, Oct 11 - Fri, Oct 23

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$420WestJet

Sun, Oct 11 - Fri, Oct 23

3:20 pm - 8:40 am

MDW

YWG

17h 20m

1 stop

9:25 am - 9:40 am

YWG

MDW

24h 15m

1 stop

$421Multiple Airlines

Tue, Jul 21 - Mon, Jul 27

9:50 am - 7:54 pm

ORD

YWG

10h 04m

1 stop

8:50 pm - 9:00 am

YWG

ORD

12h 10m

1 stop

$425Multiple Airlines

Wed, Sep 9 - Wed, Sep 16

5:30 pm - 5:25 pm

ORD

YWG

23h 55m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$433WestJet

Thu, Oct 1 - Mon, Oct 5

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$441WestJet

Mon, Aug 10 - Fri, Aug 14

7:00 am - 7:49 pm

ORD

YWG

12h 49m

1 stop

11:15 am - 11:00 am

YWG

ORD

23h 45m

2 stops

$468Porter Airlines

Thu, Oct 1 - Mon, Oct 5

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WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets

WestJet

Oct 11

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Oct 23

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$420

WestJet

Oct 1

ORD5:30 pmChicago O'Hare Intl

23h 55m

1 stop

YWG5:25 pmWinnipeg

Oct 5

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$433

WestJet

Aug 10

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Aug 14

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$441

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

Oct 1

ORD7:00 amChicago O'Hare Intl

12h 49m

1 stop

YWG7:49 pmWinnipeg

Oct 5

YWG11:15 amWinnipeg

23h 45m

2 stops

ORD11:00 amChicago O'Hare Intl

$468

Porter Airlines

Jul 21

MDW10:25 amChicago Midway

9h 29m

1 stop

YWG7:54 pmWinnipeg

Jul 26

YWG8:50 pmWinnipeg

12h 50m

1 stop

MDW9:40 amChicago Midway

$553

Porter Airlines

Jun 17

ORD11:45 amChicago O'Hare Intl

8h 04m

1 stop

YWG7:49 pmWinnipeg

Jun 24

YWG9:20 amWinnipeg

6h 58m

1 stop

ORD4:18 pmChicago O'Hare Intl

$810

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 6/25

10:25 am-8:40 am

1 stop22h 15m

Winnipeg

Mon 6/29

8:10 pm-9:40 am

1 stop13h 30m

$405

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/18

5:30 pm-11:10 am

1 stop17h 40m

Winnipeg

Sun 9/20

11:15 am-9:35 pm

2 stops10h 20m

$410

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 6/25

10:25 am-8:40 am

1 stop22h 15m

Winnipeg

Wed 7/1

6:05 pm-9:40 am

1 stop15h 35m

$418

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 10/11

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 10/23

4:15 pm-11:00 am

2 stops18h 45m

$419

Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 10/11

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 10/23

7:00 am-4:40 pm

1 stop9h 40m

$420

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/21

3:20 pm-8:40 am

1 stop17h 20m

Winnipeg

Mon 7/27

9:25 am-9:40 am

1 stop24h 15m

$421

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/9

9:50 am-7:54 pm

1 stop10h 04m

Winnipeg

Wed 9/16

8:50 pm-9:00 am

1 stop12h 10m

$425

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/1

5:30 pm-5:25 pm

1 stop23h 55m

Winnipeg

Mon 10/5

7:00 am-4:40 pm

1 stop9h 40m

$433

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 8/10

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 8/14

7:00 am-4:40 pm

1 stop9h 40m

$441

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/1

7:00 am-7:49 pm

1 stop12h 49m

Winnipeg

Mon 10/5

11:15 am-11:00 am

2 stops23h 45m

$468

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 $585. 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 $1,062.

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

The cheapest time of day to fly to Winnipeg is at noon when flights can be purchased for as low as $650. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $801 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

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 51% on your flight if you consider stops on a Chicago to Winnipeg flight.

How have Chicago to Winnipeg flight prices changed over time?

As of June 2026, prices for Chicago to Winnipeg flights are approximately 5% more expensive when compared to flights at the same time last year.

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	$804
Fastest flight time	2h 24m
Direct flights	Mon, 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 $804. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $878.

The fastest flight from Chicago to Winnipeg takes 2h 24m

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

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 June 2026, 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) (69.33% of total bookings). The next most popular plane models are Boeing 777-300ER (6.67%), Boeing 787-10 Dreamliner (5.33%), and Boeing 777-300 (5.33%).
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 $208	Free Cancellation	Rating 7.2 3,356 reviews		Search WestJet flights
United Airlines	PriceFrom $291	Free Cancellation	Rating 7.4 9,808 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Winnipeg
United Airlines flies from Chicago to Winnipeg around 13 times per week, with 9,802 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $291 (round-trip), much lower than the average airfare cost of $714 for United Airlines flights on this route.

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Portage la Prairie

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.