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$110+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Wed 12/104:35 pmORD - YWG
2 stops26h 26mMultiple Airlines
Sun 12/147:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 12/9$666
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/2210:37 amORD - YWG
1 stop33h 31mMultiple Airlines
Mon 1/58:00 amYWG - ORD
2 stops36h 04mMultiple Airlines
Deal found 12/11$707
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/115:00 amORD - YWG
2 stops14h 35mMultiple Airlines
Wed 12/174:55 pmYWG - ORD
1 stop27h 28mMultiple Airlines
Deal found 12/10$771
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:10 amORD - YWG
Nonstop2h 47mUnited Airlines
Sun 12/282:20 pmYWG - ORD
Nonstop2h 43mUnited Airlines
Deal found 12/10$806
This Air Canada deal was found by Cheapflights users on 12/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:30 pmORD - YWG
1 stop13h 19mAir Canada
Tue 12/305:30 amYWG - ORD
1 stop14h 15mAir Canada
Deal found 12/11$839
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/258:21 pmORD - YWG
2 stops29h 05mMultiple Airlines
Sun 12/285:40 pmYWG - ORD
1 stop8h 12mMultiple Airlines
Deal found 12/10$880

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$235
(Kiwi.com)

One-way from

$110
(Kiwi.com)

Popular in

July

Cheapest in

May

Average price

$699

Good round-trip deal

$680 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. 12% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Winnipeg.
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 2,558,603 searches. Data last updated December 12, 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

Fri 6/5

5:30 pm-11:40 am

1 stop18h 10m

Winnipeg

Sun 6/7

8:30 am-4:43 pm

1 stop8h 13m

$320

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 1/25

8:43 pm-12:41 am

3 stops27h 58m

Winnipeg

Sun 2/1

8:20 pm-9:03 pm

2 stops24h 43m

$354

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-11:33 am

2 stops18h 03m

Winnipeg

Mon 6/1

8:30 am-4:43 pm

1 stop8h 13m

$376

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/10

5:15 am-12:41 am

3 stops19h 26m

Winnipeg

Thu 1/15

12:10 pm-9:12 am

2 stops21h 02m

$391

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/23

7:00 am-12:39 am

2 stops17h 39m

Winnipeg

Mon 4/27

8:30 am-4:43 pm

1 stop8h 13m

$412

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/23

7:00 am-12:39 am

2 stops17h 39m

Winnipeg

Thu 4/30

8:30 am-4:43 pm

1 stop8h 13m

$412

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/30

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Mon 2/2

6:15 am-1:35 pm

1 stop7h 20m

$417

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/24

6:03 am-12:41 am

2 stops18h 38m

$113

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 1/25

2:42 pm-12:41 am

2 stops33h 59m

$116

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/24

10:00 am-5:19 pm

1 stop7h 19m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 16 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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 $89). 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 December 12, 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 December 12, 2025.
Get a feel of what it's like to fly with United Airlines, WestJet, 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
9,095 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
WestJet
7.2
Good
3,195 reviews
United Airlines
7.4
Good
9,095 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Air Canada
7.1
Good
10,516 reviews
United Airlines
7.4
Good
9,095 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 3 inbound flights from Chicago O'Hare Intl per day. 3 airlines have flights to Winnipeg from Chicago O'Hare Intl on a regular basis.

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

    Airlines like WestJet fly from Chicago O'Hare Intl Airport to Winnipeg in about 18h 10m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago O'Hare Intl Airport and Winnipeg is about 706 mi.

  • 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 $156. Other airlines that can offer you cheap pricing are Air Canada, from $230, and United Airlines, from $266. These flights start at 70% 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 (73%), United Airlines (73%) or Air Canada (70%) 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 $923 for a flight from Chicago O'Hare Intl Airport to Winnipeg. The cheapest flight overall is $322 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $241.

  • 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 $89). 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

See prices for flight routes from nearby airports that may be better suited for you.
Midway to Winnipeg flights

Top 3 airlines flying from O'Hare Intl to Winnipeg

Discover the top 3 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$675FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$645FlexibilityNo cancel feeOn-time69%

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