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Cheap flights from Chicago to Winnipeg from C$ 113

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 3/12. 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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Multiple Airlines Logo
7:23 p.m. - 3:07 p.m.MDW-YWG
19h 44m1 stop
Multiple Airlines Logo
7:30 a.m. - 6:12 p.m.YWG-MDW
10h 42m1 stop
C$ 268Multiple Airlines
Find Deal
Πεμ, 11 Δεκ - Κυρ, 14 Δεκ
Multiple Airlines Logo
7:23 p.m. - 3:07 p.m.MDW-YWG
19h 44m1 stop
Multiple Airlines Logo
7:30 a.m. - 6:12 p.m.YWG-MDW
10h 42m1 stop
C$ 276Multiple Airlines
Find Deal
Πεμ, 11 Δεκ - Κυρ, 14 Δεκ
Multiple Airlines Logo
6:05 a.m. - 3:07 p.m.ORD-YWG
9h 02m1 stop
Multiple Airlines Logo
7:30 a.m. - 10:39 p.m.YWG-ORD
15h 09m1 stop
C$ 305Multiple Airlines
Find Deal
Τετ, 24 Δεκ - Τετ, 7 Ιαν
Multiple Airlines Logo
1:24 p.m. - 3:07 p.m.ORD-YWG
25h 43m1 stop
Multiple Airlines Logo
8:00 a.m. - 11:08 a.m.YWG-ORD
27h 08m1 stop
C$ 318Multiple Airlines
Find Deal
Σαβ, 13 Δεκ - Δευ, 15 Δεκ
Multiple Airlines Logo
6:11 a.m. - 12:41 a.m.ORD-YWG
18h 30m2 stops
Multiple Airlines Logo
8:00 a.m. - 11:22 a.m.YWG-ORD
27h 22m1 stop
C$ 321Multiple Airlines
Find Deal
Δευ, 15 Δεκ - Δευ, 12 Ιαν
Multiple Airlines Logo
3:10 p.m. - 3:07 p.m.MDW-YWG
23h 57m2 stops
Multiple Airlines Logo
7:30 a.m. - 6:12 p.m.YWG-MDW
10h 42m1 stop
C$ 321Multiple Airlines
Find Deal
Πεμ, 11 Δεκ - Κυρ, 14 Δεκ
Multiple Airlines Logo
9:14 p.m. - 3:07 p.m.ORD-YWG
17h 53m2 stops
Multiple Airlines Logo
8:00 a.m. - 11:08 a.m.YWG-ORD
27h 08m1 stop
C$ 335Multiple Airlines
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Σαβ, 13 Δεκ - Δευ, 15 Δεκ
Multiple Airlines Logo
6:05 a.m. - 3:07 p.m.ORD-YWG
9h 02m1 stop
Multiple Airlines Logo
12:55 p.m. - 11:35 a.m.YWG-ORD
22h 40m2 stops
C$ 359Multiple Airlines
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Τετ, 24 Δεκ - Τετ, 7 Ιαν
Multiple Airlines Logo
7:10 a.m. - 6:03 p.m.ORD-YWG
10h 53m1 stop
Multiple Airlines Logo
8:00 a.m. - 11:22 a.m.YWG-ORD
27h 22m1 stop
C$ 381Multiple Airlines
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Δευ, 15 Δεκ - Δευ, 12 Ιαν
WestJet Logo
5:30 p.m. - 11:40 a.m.ORD-YWG
18h 10m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 387WestJet
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Παρ, 1 Μαϊ - Παρ, 8 Μαϊ

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
12 Jan
ORD2:20 p.m.Chicago O'Hare Intl
8h 21m
1 stop
YWG10:41 p.m.Winnipeg
19 Jan
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
C$ 353
Find similar
WestJet
1 May
ORD5:30 p.m.Chicago O'Hare Intl
18h 10m
1 stop
YWG11:40 a.m.Winnipeg
8 May
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 387
Find similar
WestJet
9 Feb
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
19 Feb
YWG9:00 p.m.Winnipeg
16h 35m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
C$ 388
Find similar

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets
Air Canada
26 Nov
ORD4:50 p.m.Chicago O'Hare Intl
7h 04m
1 stop
YWG11:54 p.m.Winnipeg
29 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 1,038
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Air Canada
26 Nov
ORD9:22 a.m.Chicago O'Hare Intl
2h 35m
YWG11:57 a.m.Winnipeg
29 Nov
YWG2:20 p.m.Winnipeg
2h 41m
ORD5:01 p.m.Chicago O'Hare Intl
C$ 1,181
Find similar
Air Canada
22 Nov
ORD9:22 a.m.Chicago O'Hare Intl
2h 35m
YWG11:57 a.m.Winnipeg
24 Nov
YWG8:00 a.m.Winnipeg
9h 10m
1 stop
ORD5:10 p.m.Chicago O'Hare Intl
C$ 1,309
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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 Νοεμβρίου 2025.
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

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Πεμ 11/12

7:23 p.m.-3:07 p.m.

1 stop19h 44m

Winnipeg

Κυρ 14/12

7:30 a.m.-6:12 p.m.

1 stop10h 42m

C$ 268

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Πεμ 11/12

7:23 p.m.-3:07 p.m.

1 stop19h 44m

Winnipeg

Κυρ 14/12

7:30 a.m.-6:12 p.m.

1 stop10h 42m

C$ 276

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Τετ 24/12

6:05 a.m.-3:07 p.m.

1 stop9h 02m

Winnipeg

Τετ 7/1

7:30 a.m.-10:39 p.m.

1 stop15h 09m

C$ 305

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Σαβ 13/12

1:24 p.m.-3:07 p.m.

1 stop25h 43m

Winnipeg

Δευ 15/12

8:00 a.m.-11:08 a.m.

1 stop27h 08m

C$ 318

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Δευ 15/12

6:11 a.m.-12:41 a.m.

2 stops18h 30m

Winnipeg

Δευ 12/1

8:00 a.m.-11:22 a.m.

1 stop27h 22m

C$ 321

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Πεμ 11/12

3:10 p.m.-3:07 p.m.

2 stops23h 57m

Winnipeg

Κυρ 14/12

7:30 a.m.-6:12 p.m.

1 stop10h 42m

C$ 321

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Σαβ 13/12

9:14 p.m.-3:07 p.m.

2 stops17h 53m

Winnipeg

Δευ 15/12

8:00 a.m.-11:08 a.m.

1 stop27h 08m

C$ 335

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Τετ 24/12

6:05 a.m.-3:07 p.m.

1 stop9h 02m

Winnipeg

Τετ 7/1

12:55 p.m.-11:35 a.m.

2 stops22h 40m

C$ 359

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Δευ 15/12

7:10 a.m.-6:03 p.m.

1 stop10h 53m

Winnipeg

Δευ 12/1

8:00 a.m.-11:22 a.m.

1 stop27h 22m

C$ 381

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Παρ 1/5

5:30 p.m.-11:40 a.m.

1 stop18h 10m

Winnipeg

Παρ 8/5

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 387

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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 typical price of a round-trip flight between Chicago and Winnipeg?

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Chicago is in May. Flight prices, which tend to average around C$ 380, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around C$ 447.

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

Our data shows that Tuesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 449. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Saturday is C$ 1,017.

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

In the morning is the cheapest time of day to fly from Chicago to Winnipeg when you can find flight prices for as low as C$ 449. Flying to Winnipeg in the morning is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly in the evening, with an average ticket price of C$ 942. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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 is only 1 cabin class 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 49% 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

Fastest flight time

2h 24m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Winnipeg

1 airport
The fastest flight from Chicago to Winnipeg takes 2h 24m
Direct flights go from Chicago to Winnipeg on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Winnipeg: Winnipeg (YWG)
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  • How far is Chicago to Winnipeg by plane?

    A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 4h 42m 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
Morden
Selkirk
Portage la Prairie

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.

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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