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

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

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

As of August 2026, there are 7 flights per day flying from Chicago to Winnipeg. The most common time of day flights depart is 7:00p.m., with 59% of flights taking off in the evening.

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

As of August 2026, 51 flights take off from Chicago and land in Winnipeg each week. The most common flight departure day for this route is Mon, with 16% of weekly flights 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 are updated daily.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Winnipeg Airport.

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

The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

C$ 208 Cheap Flights from Chicago to Winnipeg in 2026

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.

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 422WestJet

Fri, 2 Oct - Sun, 4 Oct

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 426WestJet

Sun, 11 Oct - Sun, 18 Oct

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 433WestJet

Tue, 29 Sep - Tue, 6 Oct

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 437WestJet

Sun, 11 Oct - Sun, 18 Oct

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 442WestJet

Sun, 11 Oct - Sun, 18 Oct

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 474WestJet

Fri, 9 Oct - Fri, 16 Oct

11:45 a.m. - 8:45 p.m.MDW Chicago Midway-YWG Winnipeg

9h 00m1 stop Toronto Island

11:15 a.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

23h 45m2 stops Montreal St Hubert Toronto Island

C$ 478Multiple Airlines

Thu, 24 Sep - Mon, 28 Sep

5:30 p.m. - 11:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

17h 40m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 480WestJet

Fri, 2 Oct - Sun, 4 Oct

5:30 p.m. - 11:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

17h 40m1 stop Calgary

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

C$ 483WestJet

Thu, 17 Sep - Sun, 20 Sep

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:10 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 30m1 stop Calgary

C$ 491WestJet

Fri, 2 Oct - Sat, 10 Oct

Cheap direct flights

Enter your travel dates to find the best prices.

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,118Lufthansa

Wed, 7 Oct - Wed, 14 Oct

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,183Lufthansa

Thu, 24 Sep - Mon, 28 Sep

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,188Air Canada

Fri, 25 Sep - Sun, 27 Sep

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,190Air Canada

Fri, 9 Oct - Fri, 16 Oct

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,193Air Canada

Fri, 9 Oct - Fri, 16 Oct

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,215Air Canada

Wed, 11 Nov - Mon, 16 Nov

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,224Air Canada

Fri, 9 Oct - Fri, 16 Oct

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,226Air Canada

Wed, 4 Nov - Wed, 11 Nov

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,229Air Canada

Wed, 7 Oct - Wed, 14 Oct

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

C$ 1,290United Airlines

Mon, 28 Sep - Tue, 29 Sep

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Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Porter Airlines

25 Sep

MDW11:45 a.m.Chicago Midway

8h 04m

1 stop

YWG7:49 p.m.Winnipeg

27 Sep

YWG8:45 p.m.Winnipeg

14h 15m

1 stop

MDW11:00 a.m.Chicago Midway

C$ 535

Porter Airlines

21 Sep

MDW3:20 p.m.Chicago Midway

19h 23m

2 stops

YWG10:43 a.m.Winnipeg

28 Sep

YWG11:40 a.m.Winnipeg

23h 20m

2 stops

MDW11:00 a.m.Chicago Midway

C$ 856

Porter Airlines

26 Sep

MDW11:45 a.m.Chicago Midway

30h 13m

2 stops

YWG5:58 p.m.Winnipeg

29 Sep

YWG11:40 a.m.Winnipeg

23h 20m

2 stops

MDW11:00 a.m.Chicago Midway

C$ 990

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets

Delta

10 Oct

MDW11:33 a.m.Chicago Midway

11h 46m

2 stops

YWG11:19 p.m.Winnipeg

17 Oct

YWG6:40 a.m.Winnipeg

11h 20m

2 stops

MDW6:00 p.m.Chicago Midway

C$ 928

Delta

10 Oct

MDW12:27 p.m.Chicago Midway

4h 23m

1 stop

YWG4:50 p.m.Winnipeg

17 Oct

YWG6:40 a.m.Winnipeg

11h 20m

2 stops

MDW6:00 p.m.Chicago Midway

C$ 975

Delta

4 Nov

MDW1:27 p.m.Chicago Midway

9h 52m

2 stops

YWG11:19 p.m.Winnipeg

11 Nov

YWG6:35 a.m.Winnipeg

5h 15m

1 stop

MDW11:50 a.m.Chicago Midway

C$ 1,012

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 4/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 422

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 18/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 426

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 29/9

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Tue 6/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 433

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 18/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 437

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 18/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 442

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 9/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Fri 16/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 474

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 24/9

11:45 a.m.-8:45 p.m.

1 stop9h 00m

Winnipeg

Mon 28/9

11:15 a.m.-11:00 a.m.

2 stops23h 45m

C$ 478

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

5:30 p.m.-11:10 a.m.

1 stop17h 40m

Winnipeg

Sun 4/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 480

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 17/9

5:30 p.m.-11:10 a.m.

1 stop17h 40m

Winnipeg

Sun 20/9

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 483

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sat 10/10

7:10 p.m.-4:40 p.m.

1 stop21h 30m

C$ 491

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 cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Chicago is in September. Flight prices, which tend to average around C$ 575, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of September, then departing from Chicago during the month October is also very affordable. Most momondo users find prices during this month for around C$ 664.

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 50% 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 August 2026, prices for Chicago to Winnipeg flights are approximately 7% cheaper 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	C$ 208
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 C$ 208. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 422.

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 1153.0 km. Typically, this will take 2h 24m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport are updated daily.
How old do you have to be to fly from Chicago to Winnipeg Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Winnipeg?
Based on momondo bookings for flights between Chicago and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 73.58% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 7.55%, Boeing 777-300ER with 7.55%, and Boeing 777-300 with 7.55%.

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Selkirk

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Winnipeg for you.

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?

momondo helps you find the best flight between Chicago and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Chicago and alert you 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 C$ 208

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 18/9. 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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Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

See travel insights to Winnipeg from

How to get the cheapest flight ticket from Chicago to Winnipeg

What is the cheapest month to fly to Winnipeg?

What is the cheapest Chicago to Winnipeg flight route?

What cabin class options are available on Chicago to Winnipeg flights?

Can stopping save me money on Chicago to Winnipeg flights?

How have Chicago to Winnipeg flight prices changed over time?

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

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

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

When to book flights from Chicago to Winnipeg

Cheap Chicago to Winnipeg (CHI to YWG) flight deals and tips

Best price found

Fastest flight time

Direct flights

Airports in Winnipeg

Frequently asked questions about flying from Chicago to Winnipeg

Travelling to a place near Winnipeg?

Why use momondo?

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

Cabin classes currently available on flights to Winnipeg

List of cabin classes available on flights landing in Winnipeg. Availability may vary depending on flight origin and airline.

Popular Cities in Canada

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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According to popular flight searches on momondo this year