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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 158

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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap 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 11 September 2025.

Round-trip from

C$ 254

One-way from

C$ 158

Popular in

July

Cheapest in

May

Average price

C$ 766

Good one-way deal

C$ 254 or less
WestJet
  • WestJet
  • 2/2-20/2
  • 2 total stops
  • 15h 40m total
  • Chicago to Winnipeg
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WestJet
  • WestJet
  • 6/10
  • 2 total stops
  • 17h 56m total
  • Chicago to Winnipeg
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Highest demand for flights based on searches. 12% potential increase in price (C$ 150 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 32 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Chicago O'Hare Intl to Winnipeg.
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Find flight deals from O'Hare Intl to Winnipeg

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 11 September 2025.

Fri 31/102:20 p.m.ORD - YWG
1 stop8h 21mWestJet
Sun 2/115:15 a.m.YWG - ORD
1 stop7h 20mWestJet
Deal found 11/9C$ 320
Thu 9/105:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Sun 12/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 10/9C$ 337
Sat 18/105:30 p.m.ORD - YWG
2 stops17h 56mWestJet
Thu 23/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 10/9C$ 342
Sun 26/102:20 p.m.ORD - YWG
1 stop10h 21mWestJet
Sun 2/115:15 a.m.YWG - ORD
1 stop7h 20mWestJet
Deal found 11/9C$ 364
Wed 8/103:12 p.m.ORD - YWG
1 stop25h 10mMultiple Airlines
Wed 15/109:05 p.m.YWG - ORD
1 stop19h 38mMultiple Airlines
Deal found 9/9C$ 367
Fri 31/105:25 a.m.ORD - YWG
2 stops13h 47mMultiple Airlines
Sun 2/115:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
Deal found 11/9C$ 387
Thu 16/105:30 p.m.ORD - YWG
2 stops17h 56mWestJet
Fri 24/1012:15 p.m.YWG - ORD
2 stops28h 28mWestJet
Deal found 10/9C$ 400

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 11 September 2025.
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

Thu 9/10

5:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Sun 12/10

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

1 stop8h 13m

C$ 337

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 8/10

3:12 p.m.-4:22 p.m.

1 stop25h 10m

Winnipeg

Wed 15/10

9:05 p.m.-4:43 p.m.

1 stop19h 38m

C$ 367

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 16/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

Winnipeg

Fri 24/10

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

1 stop8h 13m

C$ 396

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/2

5:59 p.m.-3:30 p.m.

2 stops21h 31m

Winnipeg

Wed 18/2

7:30 a.m.-10:23 p.m.

1 stop14h 53m

C$ 473

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 31/10

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

Wed 5/11

12:20 p.m.-9:43 a.m.

2 stops21h 23m

C$ 563

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 22/10

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

Nonstop2h 39m

Winnipeg

Sat 25/10

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

C$ 575

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 8/10

1:01 p.m.-3:31 p.m.

Nonstop2h 30m

Winnipeg

Wed 15/10

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 575

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 158

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 25/10

5:45 p.m.-3:07 p.m.

1 stop21h 22m

C$ 161

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 25/10

5:30 p.m.-12:09 p.m.

2 stops18h 39m

C$ 161

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 13 results
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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 month to book a flight from Chicago O'Hare Intl Airport to Winnipeg?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of C$ 123). Flying from Chicago O'Hare Intl Airport to Winnipeg in July is currently the most expensive (average of C$ 232). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 11 September 2025.

It’s typically best to fly out from Chicago O'Hare Intl Airport to Winnipeg in the morning. Doing so could potentially save you 41% on the flight price compared to flying in the evening, which is usually more expensive.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated 11 September 2025.
See what other customers who have flown with Air Canada from Chicago O'Hare Intl Airport to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Food

6.3

Boarding

7.3

Comfort

7.1

Overall

7.1

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YWG

Should allow a carry- on baggage in economy class. The first 4 rows after first class should be allowed to use the closest bathroom.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Food

6.3

Boarding

7.3

Comfort

7.1

Overall

7.1

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YWG

Should allow a carry- on baggage in economy class. The first 4 rows after first class should be allowed to use the closest bathroom.

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 6 inbound flights from Chicago O'Hare Intl per day from 1 airline. 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 18h 11m. Chicago O'Hare Intl Airport and Winnipeg are separated by a distance of 1136 km.

  • What is the cheapest airline to fly from Chicago O'Hare Intl Airport to Winnipeg round-trip?

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Winnipeg round-trip from C$ 444. This flight start at 38% lower than the current average price 3 months from now.

  • 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 (76%), Air Canada (76%), United Airlines (76%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Winnipeg?

    Looking at all options, your cheapest flight can be booked for C$ 254. While the most popular route (Chicago O'Hare Intl - Winnipeg) can be booked for C$ 353 on average, our data indicates C$ 262 when flying from Chicago O'Hare Intl Airport to Winnipeg.

  • 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.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Winnipeg?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of C$ 123). Flying from Chicago O'Hare Intl Airport to Winnipeg in July is currently the most expensive (average of C$ 232). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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.
Winnipeg car rentals
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Brandon car rentals
Thompson car rentals

Top airline flying from O'Hare Intl to Winnipeg

Discover the top airline that operate flights from O'Hare Intl to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 444AverageC$ 1,005FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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