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$76+ Cheap flights from O'Hare Intl (ORD) to Winnipeg (YWG)

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$250
(Kiwi.com)

One-way from

$76
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$632

Good round-trip deal

$1,004 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Winnipeg flights.
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From Chicago O'Hare Intl to Winnipeg
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One-way flight from Chicago O'Hare Intl to Winnipeg
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Highest demand for flights based on searches. 18% potential increase in price ($122 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Mon 12/19:00 pmYWG - ORD
2 stops18h 12mMultiple Airlines
Deal found 10/26$250
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Wed 11/267:30 amYWG - ORD
1 stop28h 04mMultiple Airlines
Deal found 10/28$264
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Mon 11/249:00 pmYWG - ORD
2 stops14h 34mMultiple Airlines
Deal found 10/26$269
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:00 amORD - YWG
1 stop9h 07mMultiple Airlines
Wed 11/267:30 amYWG - ORD
1 stop16h 38mMultiple Airlines
Deal found 10/28$290
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:53 pmORD - YWG
1 stop27h 30mMultiple Airlines
Thu 12/189:05 amYWG - ORD
2 stops10h 03mMultiple Airlines
Deal found 10/27$309
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:35 pmORD - YWG
2 stops23h 31mMultiple Airlines
Mon 12/18:00 amYWG - ORD
1 stop25h 17mMultiple Airlines
Deal found 10/26$312
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Tue 11/258:00 amYWG - ORD
1 stop25h 47mMultiple Airlines
Deal found 10/28$323
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:00 amORD - YWG
1 stop9h 07mMultiple Airlines
Sun 11/307:30 amYWG - ORD
2 stops51h 05mMultiple Airlines
Deal found 10/26$334
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Sun 11/304:55 pmYWG - ORD
2 stops37h 30mMultiple Airlines
Deal found 10/26$346
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:00 amORD - YWG
1 stop9h 07mMultiple Airlines
Sun 11/237:30 amYWG - ORD
1 stop16h 38mMultiple Airlines
Deal found 10/26$349

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 2,558,603 searches. Data last updated October 28, 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

Sat 1/10

8:48 pm-12:43 am

1 stop27h 55m

Winnipeg

Sun 1/25

6:55 pm-1:35 pm

1 stop18h 40m

$285

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 12/11

9:53 pm-1:23 am

1 stop27h 30m

Winnipeg

Thu 12/18

9:05 am-7:08 pm

2 stops10h 03m

$309

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/24

6:35 pm-6:06 pm

2 stops23h 31m

Winnipeg

Mon 12/1

8:00 am-9:17 am

1 stop25h 17m

$312

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/21

6:00 am-3:07 pm

1 stop9h 07m

Winnipeg

Sun 11/23

7:30 am-12:08 am

1 stop16h 38m

$349

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 12/23

12:32 pm-3:07 pm

1 stop26h 35m

Winnipeg

Sun 12/28

5:40 pm-1:52 am

1 stop8h 12m

$372

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 11/23

6:00 am-3:07 pm

1 stop9h 07m

Winnipeg

Tue 11/25

5:55 am-8:28 pm

2 stops14h 33m

$377

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 2/11

8:41 am-11:32 am

2 stops26h 51m

Winnipeg

Thu 2/19

4:10 pm-9:44 am

3 stops17h 34m

$421

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 12/11

11:44 am-3:07 pm

1 stop27h 23m

$76

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 12/23

12:32 pm-3:07 pm

1 stop26h 35m

$130

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 12/19

1:27 pm-1:23 am

1 stop11h 56m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 14 results
1
2

Compare providers for flights from O'Hare Intl to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Winnipeg in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Winnipeg flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Winnipeg flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Winnipeg flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of $91). Flying from Chicago O'Hare Intl Airport to Winnipeg in November is currently the most expensive (average of $614). 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 October 28, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 14% on airfare.

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 October 28, 2025.
Get a feel of what it's like to fly with United Airlines and Air Canada from Chicago O'Hare Intl Airport to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,001 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,001 reviews
United Airlines
7.4
Good
9,001 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,371 reviews
United Airlines
7.4
Good
9,001 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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?

    For a flight from Chicago O'Hare Intl to Winnipeg, you will be flying into Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city. Winnipeg is the only Winnipeg airport and it handles 2 inbound flights from Chicago O'Hare Intl per day. 2 airlines have flights to Winnipeg from Chicago O'Hare Intl on a regular basis.

  • What are the cheapest airlines flying 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 $230. Another airline that can offer you cheap pricing is United Airlines. These flights start at 57% lower than the current average price 3 months from now.

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

    Consider SkyWest Airlines (89%), Air Canada (89%) or United Airlines (89%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Winnipeg.

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

    On average you can expect to pay $1,090 for a flight from Chicago O'Hare Intl Airport to Winnipeg. The cheapest flight overall is $1,004 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $251.

  • 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, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of $91). Flying from Chicago O'Hare Intl Airport to Winnipeg in November is currently the most expensive (average of $614). 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

Traveling to a place near Winnipeg?

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

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Alternative routes for O'Hare Intl to Winnipeg

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Midway to Winnipeg flights

Top 2 airlines flying from O'Hare Intl to Winnipeg

Discover the top 2 airlines 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 2,558,603 searches. Data last updated October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$614FlexibilityNo cancel feeOn-time69%

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