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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 164

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
25 Feb — 4 Mar1
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 26 January 2026.

Wed 3/65:30 p.m.
ORD
-
YWG
1 stop7h 00m
WestJet
Thu 4/68:30 a.m.
YWG
-
ORD
1 stop8h 13m
WestJet
Deal found 25/1C$ 385
Tue 9/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 16/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 25/1C$ 386
Fri 5/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 7/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 25/1C$ 404
Mon 8/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 19/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 25/1C$ 410
Sat 6/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 15/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 25/1C$ 411
Fri 12/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 15/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 25/1C$ 416
Tue 28/44:28 p.m.
ORD
-
YWG
2 stops25h 12m
Multiple Airlines
Thu 7/58:30 a.m.
YWG
-
ORD
1 stop8h 13m
Multiple Airlines
Deal found 24/1C$ 448
Tue 3/39:15 a.m.
ORD
-
YWG
2 stops15h 26m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Deal found 26/1C$ 452
Wed 11/36:36 p.m.
ORD
-
YWG
2 stops48h 59m
Multiple Airlines
Wed 18/37:30 a.m.
YWG
-
ORD
1 stop10h 27m
Multiple Airlines
Deal found 25/1C$ 453

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 26 January 2026.

Round-trip from

C$ 385

One-way from

C$ 164

Popular in

July

Cheapest in

May

Average price

C$ 1,686
WestJet
  • WestJet
  • 3/6-4/6
  • 2 total stops
  • 15h 13m total
  • Chicago to Winnipeg
Search Deals
WestJet
  • WestJet
  • 3/6
  • 1 total stop
  • 7h 25m total
  • Chicago to Winnipeg
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 165 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 26 January 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

O'Hare Intl

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-11:00 p.m.

1 stop29h 30m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 445

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 10/3

7:41 p.m.-3:09 p.m.

1 stop19h 28m

Winnipeg

Tue 17/3

8:05 p.m.-7:46 p.m.

2 stops23h 41m

C$ 475

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

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

1 stop7h 25m

Winnipeg

Mon 1/6

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

1 stop9h 40m

C$ 510

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 12/3

4:28 p.m.-3:09 p.m.

1 stop22h 41m

Winnipeg

Thu 19/3

5:00 a.m.-11:17 p.m.

2 stops18h 17m

C$ 599

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 3/3

5:15 a.m.-12:40 a.m.

3 stops19h 25m

Winnipeg

Wed 4/3

7:30 a.m.-11:47 p.m.

2 stops16h 17m

C$ 604

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 28/4

8:36 p.m.-3:30 p.m.

1 stop18h 54m

Winnipeg

Thu 7/5

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

1 stop8h 13m

C$ 667

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 15/6

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

1 stop7h 25m

Winnipeg

Wed 17/6

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

1 stop9h 40m

C$ 671

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 6/7

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

1 stop18h 10m

Winnipeg

Fri 10/7

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

1 stop8h 13m

C$ 694

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 16/2

7:00 a.m.-6:03 p.m.

1 stop11h 03m

Winnipeg

Fri 20/2

6:15 a.m.-1:35 p.m.

1 stop7h 20m

C$ 696

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 3/6

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

1 stop7h 25m

C$ 164

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 16 results
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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 26 January 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.

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 29h 30m. Chicago O'Hare Intl Airport and Winnipeg are separated by a distance of 1136 km.

  • 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 (54%), Air Canada (54%), United Airlines (54%).

  • 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

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