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O'Hare Intl

$134+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$195
(Trip.com)

One-way from

$134
(Trip.com)

Popular in

October

Cheapest in

September

Average price

$361

Good round-trip deal

$466 or less

Good one-way deal

$247 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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Highest demand for flights based on searches. 14% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 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 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 September 17, 2025.

This Trip.com deal was found by Cheapflights users on 9/14. 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.
Sun 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Sun 10/195:30 pmORD - YWG
1 stop15h 31mWestJet
Deal found 9/14$195
This oojo deal was found by Cheapflights users on 9/15. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Sun 10/195:30 pmORD - YWG
1 stop15h 31mWestJet
Deal found 9/15$204
This Kiwi.com deal was found by Cheapflights users on 9/16. 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
Sat 10/41:40 pmORD - YWG
1 stop7h 45mWestJet
Deal found 9/16$218
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/115:30 pmYWG - ORD
1 stop23h 13mWestJet
Sat 10/185:30 pmORD - YWG
1 stop18h 11mWestJet
Deal found 9/15$222
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:05 pmYWG - ORD
1 stop19h 38mWestJet
Sun 10/195:30 pmORD - YWG
1 stop28h 00mWestJet
Deal found 9/16$231
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/309:00 pmYWG - ORD
1 stop16h 35mMultiple Airlines
Thu 11/66:06 pmORD - YWG
2 stops30h 36mMultiple Airlines
Deal found 9/15$263
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/279:00 pmYWG - ORD
2 stops14h 14mMultiple Airlines
Thu 11/206:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Deal found 9/14$274

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 September 17, 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 10/17

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-9:01 am

1 stop15h 31m

$204

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/16

6:30 am-4:43 pm

2 stops10h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-9:01 am

1 stop15h 31m

$218

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 10/12

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-2:25 pm

2 stops20h 55m

$234

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 10/11

6:30 pm-4:43 pm

1 stop22h 13m

Chicago O'Hare Intl

Sat 10/18

5:30 pm-11:26 am

2 stops17h 56m

$244

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/27

9:10 am-9:58 pm

1 stop12h 48m

Chicago O'Hare Intl

Sat 10/4

1:40 pm-9:25 pm

1 stop7h 45m

$282

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 10/11

7:40 pm-4:43 pm

2 stops21h 03m

Chicago O'Hare Intl

Sat 10/18

5:30 pm-11:26 am

2 stops17h 56m

$302

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 11/1

9:00 pm-2:35 pm

1 stop17h 35m

Chicago O'Hare Intl

Sat 11/8

6:00 am-12:41 am

2 stops18h 41m

$309

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 10/20

9:00 am-3:49 pm

1 stop6h 49m

$134

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/31

7:30 am-11:30 am

1 stop28h 00m

$162

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 11/14

7:30 am-4:56 pm

1 stop9h 26m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 13 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

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 September 17, 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.

How much does it cost to fly round-trip from Winnipeg to Chicago O'Hare Intl Airport?

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 September 17, 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
8,926 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

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
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

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
8,926 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

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 $204. 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 57% 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 (85%), SkyWest Airlines (82%), Air Canada (82%).

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

    On average you can expect to pay $536 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $174 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $244.

  • 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
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$487FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$230Average$645FlexibilityNo cancel feeOn-time67%

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