HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$171+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Aug 11 — Aug 181
Tue 8/11
Tue 8/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 12, 2026.

This Justfly.com deal was found by Cheapflights users on 7/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 10/45:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/10$277
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Thu 9/247:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 10/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/11$293
This Justfly.com deal was found by Cheapflights users on 7/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 10/25:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/8$297
This oojo deal was found by Cheapflights users on 7/8. 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.
Wed 9/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Sat 9/55:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/8$310
This oojo deal was found by Cheapflights users on 7/7. 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.
Tue 9/296:00 am
YWG
-
ORD
1 stop10h 40m
WestJet
Sun 10/45:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/7$316
This oojo deal was found by Cheapflights users on 7/8. 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.
Wed 9/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 9/65:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/8$321
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/67:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 8/135:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/8$324
This FlightHub deal was found by Cheapflights users on 7/8. 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.
Sun 9/277:10 pm
YWG
-
ORD
1 stop21h 30m
WestJet
Fri 10/25:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/8$327
This oojo deal was found by Cheapflights users on 7/7. 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.
Sat 9/57:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 9/105:30 pm
ORD
-
YWG
1 stop26h 45m
WestJet
Deal found 7/7$328
This WestJet deal was found by Cheapflights users on 7/9. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 10/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 7/9$334

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 July 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(Justfly.com)

One-way from

$171
(Kiwi.com)

Popular in

October

Cheapest in

September

Average price

$531

Good round-trip deal

$466 or less

Good one-way deal

$305 or less
Provider with most accurate pricing for Winnipeg-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Chicago O'Hare Intl flights.
Search Deals
From Winnipeg to Chicago O'Hare Intl
Search Deals
One-way flight from Winnipeg to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 11/18

7:00 am-2:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Sun 11/22

3:00 pm-9:57 pm

1 stop6h 57m

$429

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 8/3

12:15 pm-7:29 pm

1 stop7h 14m

Chicago O'Hare Intl

Fri 8/7

5:30 pm-12:55 am

1 stop7h 25m

$504

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/4

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/7

5:30 pm-11:10 am

1 stop17h 40m

$507

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 8/22

2:05 pm-7:52 pm

1 stop5h 47m

Chicago O'Hare Intl

Sat 8/29

9:15 am-11:52 am

Nonstop2h 37m

$634

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 8/24

7:00 am-9:35 am

Nonstop2h 35m

Chicago O'Hare Intl

Mon 8/31

7:54 pm-10:33 pm

Nonstop2h 39m

$655

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/30

2:00 pm-4:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 10/5

10:00 am-12:37 pm

Nonstop2h 37m

$655

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 8/21

2:00 pm-4:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Fri 8/28

9:15 am-11:52 am

Nonstop2h 37m

$655

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 9/28

2:00 pm-4:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 10/3

7:54 pm-10:33 pm

Nonstop2h 39m

$655

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 11/18

2:15 pm-4:36 pm

Nonstop2h 21m

Chicago O'Hare Intl

Sun 11/22

10:50 am-8:48 pm

1 stop9h 58m

$655

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 9/28

7:00 am-9:35 am

Nonstop2h 35m

Chicago O'Hare Intl

Mon 10/5

10:00 am-12:37 pm

Nonstop2h 37m

$655

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/9

Showing 1-10 of 19 resultsSorted by cheapest first
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, September is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $369). Flying from Winnipeg to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $881). 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 July 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.

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 July 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
9,979 reviews

Entertainment

7.1

Overall

7.4

Food

6.7

Boarding

7.7

Comfort

7.3

Crew

8.1

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
9,979 reviews
United Airlines
7.4
Good
9,979 reviews

Entertainment

7.1

Overall

7.4

Food

6.7

Boarding

7.7

Comfort

7.3

Crew

8.1

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 8 outbound flights 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 5h 47m. American Airlines provides one of the quickest options available for as low as $634. There are 706 mi between Winnipeg and Chicago O'Hare Intl Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 65% 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: Copa Airlines (90%), SkyWest Airlines (87%), United Airlines (87%).

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

    On average you can expect to pay $525 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $252 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $341.

  • 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, September is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $369). Flying from Winnipeg to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $881). 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
Benton Harbor
Rosemont
Schaumburg
Lake Geneva
Naperville
Oak Brook
Gurnee
Delavan
Oakbrook Terrace
South Holland
Libertyville
Hoffman Estates
Downers Grove
Rockford
Racine
Great Lakes
Joliet
Orland Park
Northbrook
Waukegan

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 July 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$517FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.