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O'Hare Intl

$121+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Chicago O'Hare Intl are usually found in August or October, booked 40 days in advance, depart on a Friday or Wednesday and return on a Friday

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 August 20, 2025.

Round-trip from

$223
(Kiwi.com)

One-way from

$121
(Kiwi.com)

Popular in

September

Cheapest in

August

Average price

$370

Good round-trip deal

$366 or less

Good one-way deal

$358 or less
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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High demand for flights, 4% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 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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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 August 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/38:30 amYWG - ORD
1 stop8h 13mWestJet
Mon 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
Deal found 8/18$223
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/119:00 amYWG - ORD
1 stop15h 10mMultiple Airlines
Sat 9/201:40 pmORD - YWG
1 stop7h 45mMultiple Airlines
Deal found 8/20$227
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/128:15 pmYWG - ORD
2 stops20h 30mMultiple Airlines
Sat 9/201:40 pmORD - YWG
1 stop7h 45mMultiple Airlines
Deal found 8/20$233
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/109:05 pmYWG - ORD
2 stops13h 26mMultiple Airlines
Sat 9/201:40 pmORD - YWG
1 stop7h 45mMultiple Airlines
Deal found 8/20$240
This Trip.com deal was found by Cheapflights users on 8/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:30 amYWG - ORD
1 stop8h 13mWestJet
Mon 10/205:30 pmORD - YWG
1 stop18h 11mWestJet
Deal found 8/20$245
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/249:00 amYWG - ORD
1 stop8h 21mMultiple Airlines
Mon 10/272:20 pmORD - YWG
1 stop8h 21mMultiple Airlines
Deal found 8/19$249
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/159:00 amYWG - ORD
1 stop8h 26mMultiple Airlines
Mon 9/2212:53 pmORD - YWG
2 stops28h 05mMultiple Airlines
Deal found 8/18$250
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Tue 9/238:30 amYWG - ORD
1 stop8h 13mWestJet
Thu 9/255:30 pmORD - YWG
2 stops17h 56mWestJet
Deal found 8/20$251

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 August 20, 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

Fri 10/3

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Mon 10/6

5:30 pm-9:01 am

1 stop15h 31m

$223

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/12

9:00 am-12:10 am

1 stop15h 10m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$227

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/11

9:00 am-12:10 am

1 stop15h 10m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$227

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/23

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Thu 9/25

5:30 pm-8:15 pm

1 stop26h 45m

$238

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/10

9:05 pm-10:31 am

2 stops13h 26m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$240

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/24

9:00 am-5:21 pm

1 stop8h 21m

Chicago O'Hare Intl

Mon 10/27

2:20 pm-10:41 pm

1 stop8h 21m

$249

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 9/15

9:00 am-5:26 pm

1 stop8h 26m

Chicago O'Hare Intl

Mon 9/22

12:53 pm-4:58 pm

2 stops28h 05m

$250

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/3

8:30 am-4:43 pm

1 stop8h 13m

$121

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/24

8:30 am-4:43 pm

1 stop8h 13m

$125

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/5

6:15 am-1:35 pm

1 stop7h 20m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 17 results
1
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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

How far ahead should I book a flight from Winnipeg to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to O'Hare Intl. Price data was last updated on August 8, 2025.

The price you pay for your flight from Winnipeg to Chicago O'Hare Intl Airport may vary depending on when you book. For the best chance of a lower fare, look to book 40 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $245). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 August 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 6% on flights from Winnipeg to Chicago O'Hare Intl Airport by exploring options for tickets in the morning.

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 August 20, 2025.
See what other customers who have flown with United Airlines and Air Canada 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
8,928 reviews

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,928 reviews

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 7 outbound flights to Chicago O'Hare Intl per day. 2 airlines have flights to Chicago O'Hare Intl from Winnipeg on a regular basis.

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

    A quick flight from Winnipeg to Chicago O'Hare Intl Airport can take about 8h 13m. WestJet provides one of the quickest options available for as low as $223. There are 706 mi between Winnipeg and Chicago O'Hare Intl Airport.

  • What are the cheapest airlines flying 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. Another airline that can offer you cheap pricing is Air Canada. You may be able to fly from Winnipeg to Chicago O'Hare Intl Airport for 55% less than the average price by searching for these airlines.

  • 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: Copa Airlines (89%), Avianca (89%), SkyWest Airlines (80%).

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

    On average you can expect to pay $480 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $132 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $247.

  • 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, August is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $245). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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
Hoffman Estates
Beloit
Skokie
Des Plaines
Elgin
Gurnee
Arlington Heights
Racine
Rockford
Great Lakes
Orland Park
Naperville
Merrillville
Elk Grove Village
Downers Grove
Evanston
Lake Geneva
Joliet

Browse thousands of different options on Cheapflights for your next trip

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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 2 airlines flying from Winnipeg to O'Hare Intl

Discover the top 2 airlines 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$487FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$230Average$645FlexibilityNo cancel feeOn-time67%

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