Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago to Winnipeg from C$ 186

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 15/4. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:28 a.m. - 3:09 p.m.
ORD
-
YWG
27h 41m
1 stop
Multiple Airlines Logo
9:05 p.m. - 10:23 a.m.
YWG
-
ORD
13h 18m
2 stops
C$ 440Multiple Airlines
Thu, 23 Apr - Mon, 27 Apr
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$ 448WestJet
Wed, 10 Jun - Sat, 13 Jun
Multiple Airlines Logo
6:50 a.m. - 10:10 p.m.
ORD
-
YWG
15h 20m
2 stops
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 452Multiple Airlines
Thu, 7 May - Sun, 10 May
Multiple Airlines Logo
6:50 a.m. - 10:10 p.m.
ORD
-
YWG
15h 20m
2 stops
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 456Multiple Airlines
Thu, 7 May - Sun, 10 May
Multiple Airlines Logo
9:55 a.m. - 5:15 p.m.
ORD
-
YWG
7h 20m
1 stop
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 458Multiple Airlines
Thu, 7 May - Sun, 10 May
Multiple Airlines Logo
6:00 a.m. - 10:10 p.m.
MDW
-
YWG
16h 10m
2 stops
Multiple Airlines Logo
4:25 p.m. - 9:45 a.m.
YWG
-
MDW
17h 20m
1 stop
C$ 486Multiple Airlines
Thu, 7 May - Sun, 10 May
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 7:55 a.m.
YWG
-
ORD
34h 50m
2 stops
C$ 491Multiple Airlines
Fri, 8 May - Sat, 16 May
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 10:22 a.m.
YWG
-
ORD
13h 17m
2 stops
C$ 497Multiple Airlines
Sat, 13 Jun - Mon, 22 Jun
Porter Airlines Logo
3:20 p.m. - 3:19 p.m.
MDW
-
YWG
23h 59m
1 stop
Porter Airlines Logo
7:00 p.m. - 9:45 a.m.
YWG
-
MDW
14h 45m
1 stop
C$ 555Porter Airlines
Thu, 7 May - Sun, 10 May
WestJet Logo
9:23 a.m. - 9:45 a.m.
MDW
-
YWG
24h 22m
2 stops
WestJet Logo
6:40 a.m. - 5:56 p.m.
YWG
-
MDW
11h 16m
1 stop
C$ 718WestJet
Fri, 15 May - Sun, 17 May

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
10 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
13 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 448
WestJet
11 May
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
1 Jun
YWG7:10 p.m.Winnipeg
21h 30m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 543
WestJet
10 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
11 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 566

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets
Porter Airlines
7 May
MDW3:20 p.m.Chicago Midway
23h 59m
1 stop
YWG3:19 p.m.Winnipeg
10 May
YWG7:00 p.m.Winnipeg
14h 45m
1 stop
MDW9:45 a.m.Chicago Midway
C$ 555
Porter Airlines
11 May
MDW3:20 p.m.Chicago Midway
23h 58m
2 stops
YWG3:18 p.m.Winnipeg
1 Jun
YWG11:40 a.m.Winnipeg
22h 00m
2 stops
MDW9:40 a.m.Chicago Midway
C$ 832
Porter Airlines
11 May
MDW3:20 p.m.Chicago Midway
23h 58m
2 stops
YWG3:18 p.m.Winnipeg
1 Jun
YWG4:15 p.m.Winnipeg
17h 25m
2 stops
MDW9:40 a.m.Chicago Midway
C$ 865

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 3 April 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

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 23/4

11:28 a.m.-3:09 p.m.

1 stop27h 41m

Winnipeg

Mon 27/4

9:05 p.m.-10:23 a.m.

2 stops13h 18m

C$ 440

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/6

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

1 stop7h 25m

Winnipeg

Sat 13/6

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

1 stop9h 40m

C$ 448

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 7/5

6:50 a.m.-10:10 p.m.

2 stops15h 20m

Winnipeg

Sun 10/5

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

1 stop9h 40m

C$ 452

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 7/5

6:50 a.m.-10:10 p.m.

2 stops15h 20m

Winnipeg

Sun 10/5

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

1 stop9h 40m

C$ 456
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 7/5

9:55 a.m.-5:15 p.m.

1 stop7h 20m

Winnipeg

Sun 10/5

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

1 stop9h 40m

C$ 458

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/5

6:00 a.m.-10:10 p.m.

2 stops16h 10m

Winnipeg

Sun 10/5

4:25 p.m.-9:45 a.m.

1 stop17h 20m

C$ 486

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 8/5

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

1 stop7h 25m

Winnipeg

Sat 16/5

9:05 p.m.-7:55 a.m.

2 stops34h 50m

C$ 491

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 13/6

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

1 stop7h 25m

Winnipeg

Mon 22/6

9:05 p.m.-10:22 a.m.

2 stops13h 17m

C$ 497

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/5

3:20 p.m.-3:19 p.m.

1 stop23h 59m

Winnipeg

Sun 10/5

7:00 p.m.-9:45 a.m.

1 stop14h 45m

C$ 555

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 15/5

9:23 a.m.-9:45 a.m.

2 stops24h 22m

Winnipeg

Sun 17/5

6:40 a.m.-5:56 p.m.

1 stop11h 16m

C$ 718

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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$ 395, 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 February is also very affordable. Most momondo users find prices during this month for around C$ 515.

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$ 437. 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$ 935. 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 61% 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

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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 3/5
Sun 10/5
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada