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Cheap flights from Chicago to Winnipeg from C$ 227

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 8/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:45 a.m. - 8:45 p.m.MDW  Chicago Midway-YWG Winnipeg
9h 00m1 stop Toronto Island
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Island
C$ 446Multiple Airlines
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
11:45 a.m. - 8:45 p.m.MDW  Chicago Midway-YWG Winnipeg
9h 00m1 stop Toronto Island
Multiple Airlines Logo
7:45 a.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
27h 15m1 stop Toronto Pearson Intl
C$ 447Multiple Airlines
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
11:45 a.m. - 8:45 p.m.MDW  Chicago Midway-YWG Winnipeg
9h 00m1 stop Toronto Island
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Pearson Intl
C$ 456Multiple Airlines
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.MDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Island
C$ 460Multiple Airlines
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.MDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Island
C$ 475Multiple Airlines
Fri, 11 Sep - Sun, 13 Sep
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.MDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
Multiple Airlines Logo
7:45 a.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
27h 15m1 stop Toronto Pearson Intl
C$ 481Multiple Airlines
Fri, 11 Sep - Sun, 13 Sep
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.MDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Island
C$ 486Multiple Airlines
Fri, 11 Sep - Sun, 13 Sep
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.MDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
Multiple Airlines Logo
6:05 p.m. - 11:00 a.m.YWG  Winnipeg-MDW Chicago Midway
16h 55m1 stop Toronto Pearson Intl
C$ 488Multiple Airlines
Fri, 11 Sep - Sun, 13 Sep
Multiple Airlines Logo
7:11 a.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
17h 44m2 stops Fort Lauderdale Toronto Pearson Intl
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 490Multiple Airlines
Thu, 17 Sep - Sun, 20 Sep
Multiple Airlines Logo
7:11 a.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
17h 44m2 stops Fort Lauderdale Toronto Pearson Intl
Multiple Airlines Logo
9:05 p.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
19h 35m1 stop Calgary
C$ 511Multiple Airlines
Thu, 24 Sep - Thu, 1 Oct

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Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets
Porter Airlines
10 Sep
MDW11:45 a.m.Chicago Midway
8h 04m
1 stop
YWG7:49 p.m.Winnipeg
13 Sep
YWG8:45 p.m.Winnipeg
14h 15m
1 stop
MDW11:00 a.m.Chicago Midway
C$ 528
Porter Airlines
10 Sep
MDW11:45 a.m.Chicago Midway
8h 04m
1 stop
YWG7:49 p.m.Winnipeg
13 Sep
YWG8:45 p.m.Winnipeg
14h 15m
1 stop
MDW11:00 a.m.Chicago Midway
C$ 543
Porter Airlines
25 Aug
MDW3:15 p.m.Chicago Midway
28h 39m
1 stop
YWG7:54 p.m.Winnipeg
1 Sep
YWG11:15 a.m.Winnipeg
27h 20m
2 stops
MDW2:35 p.m.Chicago Midway
C$ 710

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
11 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
18 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 444
WestJet
11 Sep
ORD5:30 p.m.Chicago O'Hare Intl
16h 05m
2 stops
YWG9:35 a.m.Winnipeg
18 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 553
WestJet
17 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
20 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 559

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 13 August 2026.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 10/9

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

1 stop9h 00m

Winnipeg

Sun 13/9

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

2 stops23h 45m

C$ 446

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 10/9

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

1 stop9h 00m

Winnipeg

Sun 13/9

7:45 a.m.-11:00 a.m.

1 stop27h 15m

C$ 447

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 10/9

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

1 stop9h 00m

Winnipeg

Sun 13/9

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

2 stops23h 45m

C$ 456

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 10/9

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Sun 13/9

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

2 stops23h 45m

C$ 460

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 11/9

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Sun 13/9

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

2 stops23h 45m

C$ 475

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 11/9

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Sun 13/9

7:45 a.m.-11:00 a.m.

1 stop27h 15m

C$ 481

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 11/9

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Sun 13/9

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

2 stops23h 45m

C$ 486
Quickest round-trip

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 11/9

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Sun 13/9

6:05 p.m.-11:00 a.m.

1 stop16h 55m

C$ 488

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 17/9

7:11 a.m.-12:55 a.m.

2 stops17h 44m

Winnipeg

Sun 20/9

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

1 stop9h 40m

C$ 490

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 24/9

7:11 a.m.-12:55 a.m.

2 stops17h 44m

Winnipeg

Thu 1/10

9:05 p.m.-4:40 p.m.

1 stop19h 35m

C$ 511

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Winnipeg from

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?

The cheapest month to fly to Winnipeg from Chicago is in September. Flight prices, which tend to average around C$ 606, 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$ 683.

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 58% 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 18% 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

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
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?

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie
Morden
Selkirk

Why use momondo?

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.

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