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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 237

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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
10 Jul — 17 Jul1
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 June 2026.

Fri 18/95:30 p.m.
ORD
-
YWG
1 stop17h 40m
Multiple Airlines
Sun 20/911:15 a.m.
YWG
-
ORD
2 stops10h 20m
Multiple Airlines
Deal found 5/6C$ 572
Sun 11/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Fri 23/104:15 p.m.
YWG
-
ORD
2 stops18h 45m
Multiple Airlines
Deal found 9/6C$ 584
Sun 11/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 23/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 9/6C$ 586
Wed 9/99:50 a.m.
ORD
-
YWG
1 stop10h 04m
Multiple Airlines
Wed 16/98:50 p.m.
YWG
-
ORD
1 stop12h 10m
Multiple Airlines
Deal found 9/6C$ 593
Thu 1/105:30 p.m.
ORD
-
YWG
1 stop23h 55m
WestJet
Mon 5/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 8/6C$ 604
Mon 10/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 14/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 8/6C$ 615
Wed 2/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 5/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 10/6C$ 641
Thu 1/107:00 a.m.
ORD
-
YWG
1 stop12h 49m
Porter Airlines
Mon 5/1011:15 a.m.
YWG
-
ORD
2 stops23h 45m
Porter Airlines
Deal found 8/6C$ 653
Thu 27/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 30/82:55 p.m.
YWG
-
ORD
1 stop25h 45m
WestJet
Deal found 8/6C$ 700
Tue 7/75:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Fri 10/712:15 p.m.
YWG
-
ORD
1 stop7h 14m
Multiple Airlines
Deal found 10/6C$ 703
Mon 3/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 9/88:45 p.m.
YWG
-
ORD
2 stops39h 30m
Multiple Airlines
Deal found 10/6C$ 706

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 June 2026.

Round-trip from

C$ 572

One-way from

C$ 237

Popular in

February

Cheapest in

June

Average price

C$ 540
Porter Airlines
  • Porter Airlines
  • 18/9-20/9
  • 3 total stops
  • 28h 00m total
  • Chicago to Winnipeg
Search Deals
9/9
  • 9/9
  • 1 total stop
  • 10h 04m total
  • Chicago to Winnipeg
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 434 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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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 June 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

Wed 16/9

9:45 a.m.-7:54 p.m.

1 stop10h 09m

Winnipeg

Sat 19/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 827

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 16/9

3:45 p.m.-11:07 p.m.

1 stop7h 22m

Winnipeg

Sat 19/9

5:10 a.m.-2:52 p.m.

2 stops9h 42m

C$ 872

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 4/9

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

1 stop7h 25m

Winnipeg

Mon 7/9

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

1 stop19h 35m

C$ 901

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 5/7

5:30 p.m.-4:00 p.m.

2 stops22h 30m

Winnipeg

Sun 12/7

6:00 a.m.-5:29 p.m.

3 stops11h 29m

C$ 930

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 28/6

8:35 p.m.-7:49 p.m.

1 stop23h 14m

Winnipeg

Tue 30/6

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 1,036

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 21/11

1:35 p.m.-11:34 p.m.

2 stops9h 59m

Winnipeg

Sat 28/11

12:30 p.m.-7:34 p.m.

1 stop7h 04m

C$ 1,054

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 7/7

5:35 p.m.-11:20 p.m.

1 stop5h 45m

Winnipeg

Fri 10/7

12:56 p.m.-3:30 p.m.

Nonstop2h 34m

C$ 1,068

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 8/7

9:14 a.m.-11:52 a.m.

Nonstop2h 38m

Winnipeg

Tue 14/7

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

Nonstop2h 34m

C$ 1,206

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 16/9

7:54 p.m.-10:33 p.m.

Nonstop2h 39m

Winnipeg

Sat 19/9

7:00 a.m.-9:35 a.m.

Nonstop2h 35m

C$ 1,206
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 28/10

9:15 a.m.-11:39 a.m.

Nonstop2h 24m

Winnipeg

Mon 2/11

2:15 p.m.-4:36 p.m.

Nonstop2h 21m

C$ 1,206

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 19 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 June 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 7 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 7h 22m. 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: Copa Airlines (100%), SkyWest Airlines (86%), Air Canada (86%).

  • 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

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Selkirk

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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