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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 25/8. 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.
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 476WestJet
Thu, 10 Sep - Mon, 14 Sep
WestJet Logo
5:30 p.m. - 11:10 a.m.
ORD
-
YWG
17h 40m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 496WestJet
Thu, 15 Oct - Mon, 19 Oct
WestJet Logo
5:30 p.m. - 11:10 a.m.
ORD
-
YWG
17h 40m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 530WestJet
Thu, 17 Sep - Thu, 24 Sep
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.
YWG
-
ORD
23h 45m
2 stops
C$ 536Multiple Airlines
Thu, 10 Sep - Sun, 13 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:10 p.m. - 4:40 p.m.
YWG
-
ORD
21h 30m
1 stop
C$ 539WestJet
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
11:15 a.m. - 9:35 p.m.
YWG
-
ORD
10h 20m
2 stops
C$ 540Multiple Airlines
Thu, 10 Sep - Mon, 14 Sep
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.
YWG
-
ORD
23h 45m
2 stops
C$ 542Multiple Airlines
Thu, 17 Sep - Thu, 24 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 560WestJet
Wed, 19 Aug - Wed, 26 Aug
Delta Logo
4:39 p.m. - 3:08 p.m.
MDW
-
YWG
22h 29m
2 stops
Delta Logo
3:58 p.m. - 9:59 a.m.
YWG
-
MDW
18h 01m
2 stops
C$ 747Delta
Sat, 22 Aug - Sat, 29 Aug
Porter Airlines Logo
3:15 p.m. - 10:43 a.m.
MDW
-
YWG
19h 28m
2 stops
Porter Airlines Logo
4:15 p.m. - 9:45 a.m.
YWG
-
MDW
17h 30m
2 stops
C$ 888Porter Airlines
Wed, 19 Aug - Wed, 26 Aug

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Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets
Porter Airlines
19 Aug
MDW3:15 p.m.Chicago Midway
19h 28m
2 stops
YWG10:43 a.m.Winnipeg
26 Aug
YWG4:15 p.m.Winnipeg
17h 30m
2 stops
MDW9:45 a.m.Chicago Midway
C$ 888
Porter Airlines
22 Jul
ORD9:45 a.m.Chicago O'Hare Intl
10h 09m
1 stop
YWG7:54 p.m.Winnipeg
27 Jul
YWG12:15 p.m.Winnipeg
7h 14m
1 stop
ORD7:29 p.m.Chicago O'Hare Intl
C$ 985
Porter Airlines
14 Jul
ORD9:45 a.m.Chicago O'Hare Intl
10h 09m
1 stop
YWG7:54 p.m.Winnipeg
28 Jul
YWG9:20 a.m.Winnipeg
6h 59m
1 stop
ORD4:19 p.m.Chicago O'Hare Intl
C$ 1,001

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
1 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
4 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 447
WestJet
27 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
4 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 464
WestJet
10 Sep
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
14 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 476

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 9 July 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
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/9

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

1 stop7h 25m

Winnipeg

Mon 14/9

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

1 stop9h 40m

C$ 476

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 15/10

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

1 stop17h 40m

Winnipeg

Mon 19/10

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

1 stop9h 40m

C$ 496

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 17/9

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

1 stop17h 40m

Winnipeg

Thu 24/9

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

1 stop9h 40m

C$ 530

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/9

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

1 stop7h 25m

Winnipeg

Sun 13/9

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

2 stops23h 45m

C$ 536

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/9

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

1 stop7h 25m

Winnipeg

Sun 13/9

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

1 stop21h 30m

C$ 539

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/9

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

1 stop7h 25m

Winnipeg

Mon 14/9

11:15 a.m.-9:35 p.m.

2 stops10h 20m

C$ 540

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 17/9

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

1 stop7h 25m

Winnipeg

Thu 24/9

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

2 stops23h 45m

C$ 542

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 19/8

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

1 stop7h 25m

Winnipeg

Wed 26/8

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

1 stop9h 40m

C$ 560

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 22/8

4:39 p.m.-3:08 p.m.

2 stops22h 29m

Winnipeg

Sat 29/8

3:58 p.m.-9:59 a.m.

2 stops18h 01m

C$ 747

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 19/8

3:15 p.m.-10:43 a.m.

2 stops19h 28m

Winnipeg

Wed 26/8

4:15 p.m.-9:45 a.m.

2 stops17h 30m

C$ 888

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 February. Flight prices, which tend to average around C$ 88, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of February, then departing from Chicago during the month October is also very affordable. Most momondo users find prices during this month for around C$ 115.

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 July 2026, prices for Chicago to Winnipeg flights are approximately 129% 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
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

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