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O'Hare Intl

$129+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 5/35:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 2/9$205
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Tue 5/265:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 2/9$207
This oojo deal was found by Cheapflights users on 2/9. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Wed 6/35:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 2/9$209
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:55 pm
YWG
-
ORD
1 stop25h 45m
WestJet
Sun 5/105:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 2/9$237
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Fri 5/17:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 5/35:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 2/9$264
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 5/14:55 pm
YWG
-
ORD
2 stops24h 46m
Multiple Airlines
Sun 5/35:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 2/10$269
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Sat 3/79:00 pm
YWG
-
ORD
2 stops12h 52m
Multiple Airlines
Tue 3/107:41 pm
ORD
-
YWG
1 stop19h 28m
Multiple Airlines
Deal found 2/11$274

Find 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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$205
(Trip.com)

One-way from

$129
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$496

Good round-trip deal

$291 or less

Good one-way deal

$253 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
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Winnipeg to Chicago O'Hare Intl.
Search Deals

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 February 12, 2026.
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 5/21

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 5/26

5:30 pm-12:55 am

1 stop7h 25m

$207

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/29

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Wed 6/3

5:30 pm-12:55 am

1 stop7h 25m

$209

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 4/30

7:00 am-4:40 pm

2 stops9h 40m

Chicago O'Hare Intl

Sun 5/3

5:30 pm-12:55 am

1 stop7h 25m

$217

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/14

9:05 pm-10:44 am

2 stops13h 39m

Chicago O'Hare Intl

Sun 5/17

5:30 pm-12:55 am

1 stop7h 25m

$275

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/20

5:05 pm-11:59 pm

1 stop30h 54m

Chicago O'Hare Intl

Tue 3/24

8:55 pm-6:05 pm

2 stops21h 10m

$289

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 3/9

8:00 am-10:36 am

1 stop26h 36m

Chicago O'Hare Intl

Mon 3/16

2:20 pm-10:40 pm

1 stop8h 20m

$334

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 3/11

7:30 am-5:57 pm

1 stop10h 27m

Chicago O'Hare Intl

Wed 3/18

4:36 pm-3:12 pm

2 stops22h 36m

$347

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/14

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 5/18

5:30 pm-12:55 am

1 stop7h 25m

$366

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 5/9

9:05 pm-10:44 am

2 stops13h 39m

Chicago O'Hare Intl

Sat 6/13

5:30 pm-12:55 am

1 stop7h 25m

$374

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/14

9:05 pm-10:44 am

2 stops13h 39m

Chicago O'Hare Intl

Mon 5/18

5:30 pm-12:55 am

1 stop7h 25m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 18 results
1
2
  • Most accurate provider: When it comes to deals on Winnipeg-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January is currently the most expensive (average of $515). 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 February 12, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Chicago O'Hare Intl Airport as you normally would.

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 February 12, 2026.
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
9,283 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,283 reviews
United Airlines
7.4
Good
9,283 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 1 outbound flight to Chicago O'Hare Intl per day. 1 airline has 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 9h 40m. WestJet provides one of the quickest options available for as low as $207. There are 706 mi between Winnipeg and Chicago O'Hare Intl Airport.

  • 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 57% 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 (78%), Air Canada (78%), United Airlines (78%).

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

    On average you can expect to pay $420 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $218 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $245.

  • 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 January is currently the most expensive (average of $515). 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
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

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 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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$471FlexibilityNo cancel feeOn-time69%

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