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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 148

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
9 Apr — 16 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from O'Hare Intl to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from O'Hare Intl to Winnipeg
Explore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 March 2026.

Mon 25/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Wed 27/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 5/3C$ 351
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 19/59:05 p.m.
YWG
-
ORD
2 stops13h 39m
Multiple Airlines
Deal found 9/3C$ 373
Tue 9/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 12/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 9/3C$ 379
Tue 21/46:08 p.m.
ORD
-
YWG
1 stop21h 01m
Multiple Airlines
Tue 28/49:05 p.m.
YWG
-
ORD
2 stops19h 55m
Multiple Airlines
Deal found 7/3C$ 396
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop17h 40m
WestJet
Tue 19/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 9/3C$ 399
Thu 14/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 22/59:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 5/3C$ 404
Fri 24/42:20 p.m.
ORD
-
YWG
1 stop8h 20m
Multiple Airlines
Fri 1/59:05 p.m.
YWG
-
ORD
2 stops14h 28m
Multiple Airlines
Deal found 9/3C$ 413
Fri 24/42:20 p.m.
ORD
-
YWG
1 stop8h 20m
Multiple Airlines
Mon 27/49:05 p.m.
YWG
-
ORD
2 stops12h 57m
Multiple Airlines
Deal found 6/3C$ 421
Fri 10/42:20 p.m.
ORD
-
YWG
1 stop10h 20m
Multiple Airlines
Mon 20/49:00 p.m.
YWG
-
ORD
2 stops20h 00m
Multiple Airlines
Deal found 5/3C$ 430
Sun 19/45:59 a.m.
ORD
-
YWG
1 stop9h 10m
Multiple Airlines
Sun 26/48:00 a.m.
YWG
-
ORD
1 stop8h 40m
Multiple Airlines
Deal found 5/3C$ 442

Find flight deals from O'Hare Intl to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 10 March 2026.

Round-trip from

C$ 351

One-way from

C$ 148

Popular in

February

Cheapest in

April

Average price

C$ 434
WestJet
  • WestJet
  • 25/5-27/5
  • 2 total stops
  • 17h 05m total
  • Chicago to Winnipeg
Search Deals
WestJet
  • WestJet
  • 29/5
  • 1 total stop
  • 7h 25m total
  • Chicago to Winnipeg
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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, Cheapflights users made 629,999 searches. Data last updated 10 March 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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

Sat 11/4

8:06 a.m.-3:30 p.m.

1 stop7h 24m

Winnipeg

Tue 14/4

12:10 p.m.-8:20 p.m.

1 stop8h 10m

C$ 840

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 2/4

7:31 p.m.-3:30 p.m.

2 stops19h 59m

Winnipeg

Sun 5/4

8:20 p.m.-7:15 a.m.

1 stop10h 55m

C$ 946

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/4

9:18 a.m.-11:52 a.m.

Nonstop2h 34m

Winnipeg

Sun 12/4

2:00 p.m.-4:35 p.m.

Nonstop2h 35m

C$ 985
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

9:18 a.m.-11:52 a.m.

Nonstop2h 34m

Winnipeg

Mon 1/6

7:00 a.m.-9:34 a.m.

Nonstop2h 34m

C$ 988

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 8/4

9:18 a.m.-11:52 a.m.

Nonstop2h 34m

Winnipeg

Thu 9/4

2:00 p.m.-4:35 p.m.

Nonstop2h 35m

C$ 1,000

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 8/7

7:55 p.m.-10:33 p.m.

Nonstop2h 38m

Winnipeg

Tue 14/7

7:00 a.m.-9:34 a.m.

Nonstop2h 34m

C$ 1,000
Cheapest one-way

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 31/8

12:00 p.m.-3:25 p.m.

2 stops27h 25m

C$ 280

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 12/4

7:55 a.m.-12:40 a.m.

3 stops40h 45m

C$ 284
Quickest one-way

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 14/6

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

1 stop7h 25m

C$ 307

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 20/4

10:07 p.m.-12:40 a.m.

3 stops26h 33m

C$ 309

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/3

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Best time to book a flight from O'Hare Intl to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Winnipeg

What is the cheapest time of day to fly from ORD to YWG?

Find hourly flight availability from O'Hare Intl to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 10 March 2026.

When flying from Chicago O'Hare Intl Airport to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Winnipeg?

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago O'Hare Intl?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago O'Hare Intl. On average, Winnipeg has 3 inbound flights from Chicago O'Hare Intl per day from 0 airlines. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

  • How long is the flight from Chicago O'Hare Intl Airport to Winnipeg?

    Departing from Chicago O'Hare Intl Airport to Winnipeg will take you 2h 34m. Chicago O'Hare Intl Airport and Winnipeg are separated by a distance of 1136 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Winnipeg?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago O'Hare Intl Airport to Winnipeg on time: SkyWest Airlines (67%), Air Canada (67%), United Airlines (67%).

  • Can I find deals for flights from O'Hare Intl to Winnipeg that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Winnipeg.

  • Can I find deals for business class flights from O'Hare Intl to Winnipeg?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Winnipeg?

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

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Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
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Brandon car rentals
Thompson car rentals

Fly with Cheapflights

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How does Cheapflights help users find flights from O'Hare Intl to Winnipeg?

Cheapflights helps you search for flights from O'Hare Intl to Winnipeg via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from O'Hare Intl to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from O'Hare Intl.

Can Cheapflights find flights from O'Hare Intl to Winnipeg with no change fees?

Certainly. Search results for flights to Winnipeg from O'Hare Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from O'Hare Intl to Winnipeg become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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