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O'Hare Intl

$118+ Cheap flights from Winnipeg (YWG) to O'Hare Intl (ORD)

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Dec 31 — Jan 71
Wed 12/31
Wed 1/7
1 adult, Economy
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Find flight deals from Winnipeg to O'Hare Intl

Cheapest flights from Winnipeg to O'Hare Intl
Explore the most affordable flight options available from Winnipeg to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/68:20 pmYWG - ORD
2 stops40h 56mMultiple Airlines
Sat 12/131:24 pmORD - YWG
1 stop25h 43mMultiple Airlines
Deal found 12/1$475
This Air Canada deal was found by Cheapflights users on 11/30. 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.
Thu 12/255:30 amYWG - ORD
1 stop7h 31mAir Canada
Tue 1/63:55 pmORD - YWG
1 stop7h 59mAir Canada
Deal found 11/30$528
This FlightHub deal was found by Cheapflights users on 11/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:45 pmYWG - ORD
1 stop18h 05mWestJet
Mon 1/56:15 amORD - YWG
2 stops18h 24mWestJet
Deal found 11/29$550
This Expedia deal was found by Cheapflights users on 11/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:45 amYWG - ORD
2 stops14h 49mWestJet
Tue 1/61:55 pmORD - YWG
2 stops10h 47mWestJet
Deal found 11/30$575
This WestJet deal was found by Cheapflights users on 11/30. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:45 pmYWG - ORD
1 stop23h 12mWestJet
Wed 12/176:00 amORD - YWG
1 stop5h 45mWestJet
Deal found 11/30$591
This United Airlines deal was found by Cheapflights users on 11/30. 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.
Mon 12/292:20 pmYWG - ORD
Nonstop2h 43mUnited Airlines
Thu 1/19:29 pmORD - YWG
2 stops22h 05mUnited Airlines
Deal found 11/30$605

Cheap flight deals from Winnipeg to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to O'Hare Intl (ORD). 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 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$235
(Kiwi.com)

One-way from

$118
(Trip.com)

Popular in

November

Cheapest in

September

Average price

$559

Good round-trip deal

$357 or less

Good one-way deal

$268 or less
Provider with most accurate pricing for Winnipeg-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Chicago O'Hare Intl flights.
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From Winnipeg to Chicago O'Hare Intl
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One-way flight from Winnipeg to Chicago O'Hare Intl
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Highest demand for flights based on searches. 28% potential increase in price ($203 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Winnipeg to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Winnipeg to Chicago O'Hare Intl.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to O'Hare Intl 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 1, 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago O'Hare Intl Airport that are best for you.

Fly from

Winnipeg

Fly to

O'Hare Intl

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/15

6:55 pm-1:35 pm

1 stop18h 40m

Chicago O'Hare Intl

Sun 1/18

6:20 am-3:07 pm

1 stop8h 47m

$235

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/15

9:00 pm-1:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Thu 1/22

5:40 am-12:41 am

2 stops19h 01m

$246

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 1/10

12:10 pm-8:04 pm

1 stop7h 54m

Chicago O'Hare Intl

Mon 1/12

2:20 pm-10:41 pm

1 stop8h 21m

$284

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 12/8

9:00 pm-6:46 pm

2 stops21h 46m

$118

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 1/14

4:10 pm-7:36 pm

2 stops27h 26m

$139

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/15

9:00 pm-1:35 pm

1 stop16h 35m

$141

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/15

12:55 pm-9:11 pm

3 stops32h 16m

$142

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 1/5

4:55 pm-8:02 pm

2 stops27h 07m

$220

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/15

2:20 pm-5:03 pm

Nonstop2h 43m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/28

Compare providers for flights from Winnipeg to O'Hare Intl

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 Winnipeg to O'Hare Intl in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Winnipeg-Chicago O'Hare Intl Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Winnipeg-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Chicago O'Hare Intl Airport 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 Winnipeg-Chicago O'Hare Intl Airport 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 Winnipeg to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Winnipeg 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 Winnipeg to Chicago O'Hare Intl Airport

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

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $145). Flying from Winnipeg to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $435). 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 YWG to ORD?

Find hourly flight availability from Winnipeg to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 1, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 7% on flights from Winnipeg to Chicago O'Hare Intl Airport by exploring options for tickets in the afternoon.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated December 1, 2025.
See what other customers who have flown with United Airlines from Winnipeg to Chicago O'Hare Intl Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,056 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,056 reviews
United Airlines
7.4
Good
9,056 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to O'Hare Intl. 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 from for flights from Winnipeg to Chicago O'Hare Intl?

    For a flight from Winnipeg to Chicago O'Hare Intl, you will be flying from Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city. Winnipeg is the only Winnipeg airport and it handles 4 outbound flights to Chicago O'Hare Intl per day. 1 airline has flights to Chicago O'Hare Intl from Winnipeg on a regular basis.

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

    Cheapflights users have booked flights from Winnipeg to Chicago O'Hare Intl Airport round-trip from $199. You may be able to fly from Winnipeg to Chicago O'Hare Intl Airport for 60% less than the average price by searching for this airline.

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

    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 Winnipeg to Chicago O'Hare Intl Airport on time: SkyWest Airlines (84%), Air Canada (84%), United Airlines (84%).

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

    On average you can expect to pay $552 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $148 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $211.

  • Can I find deals for flights from Winnipeg to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Winnipeg to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to O'Hare Intl.

  • Can I find deals for business class flights from Winnipeg to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Winnipeg to O'Hare Intl 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 Winnipeg to Chicago O'Hare Intl Airport?

    Currently, May is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $145). Flying from Winnipeg to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $435). 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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Alternative routes for Winnipeg to O'Hare Intl

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

Top airline flying from Winnipeg to O'Hare Intl

Discover the top airline that operate flights from Winnipeg to O'Hare Intl. 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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$471FlexibilityNo cancel feeOn-time69%

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