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O'Hare Intl

$185+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Sep 12 — Sep 191
Sat 9/12
Sat 9/19
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 August 13, 2026.

This FlightHub deal was found by Cheapflights users on 8/12. 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.
Fri 9/187:00 am -
1 stop9h 40m
Mon 9/215:30 pm -
1 stop7h 25m
Deal found 8/12$258
This Justfly.com deal was found by Cheapflights users on 8/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/9$351
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 10/167:00 am -
1 stop9h 40m
Thu 10/227:45 am -
2 stops17h 10m
Deal found 8/10$368
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sun 10/187:00 am -
1 stop9h 40m
Thu 10/227:45 am -
2 stops17h 10m
Deal found 8/10$369
This Mytrip deal was found by Cheapflights users on 8/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:05 pm -
1 stop14h 55m
Tue 9/299:55 am -
1 stop9h 54m
Deal found 8/8$370

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 August 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$351
(Justfly.com)

One-way from

$185
(Kiwi.com)

Popular in

October

Cheapest in

September

Average price

$639

Good round-trip deal

$551 or less

Good one-way deal

$384 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. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in August 2026
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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 August 13, 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 Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 9/10

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 9/13

5:30 pm-12:55 am

1 stop7h 25m

$365

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/10

7:10 pm-4:40 pm

1 stop21h 30m

Chicago O'Hare Intl

Sat 10/17

7:44 pm-3:25 pm

2 stops19h 41m

$416

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/31

6:15 am-7:44 pm

2 stops13h 29m

Chicago O'Hare Intl

Fri 11/6

4:00 pm-12:43 am

1 stop8h 43m

$446

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 9/12

12:20 pm-7:48 pm

1 stop7h 28m

Chicago O'Hare Intl

Tue 9/15

9:55 am-4:27 pm

1 stop6h 32m

$496

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 9/17

10:30 pm-4:40 pm

2 stops18h 10m

Chicago O'Hare Intl

Sun 9/20

5:30 pm-12:55 am

1 stop7h 25m

$508

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 8/28

7:10 pm-4:51 pm

2 stops21h 41m

Chicago O'Hare Intl

Sun 8/30

5:30 pm-12:55 am

1 stop7h 25m

$513

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 9/16

11:40 am-8:20 pm

2 stops8h 40m

Chicago O'Hare Intl

Sat 9/19

8:03 am-3:19 pm

1 stop7h 16m

$520

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 9/30

9:20 am-4:18 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 9/30

8:30 pm-10:43 am

2 stops14h 13m

$557
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 9/6

3:20 pm-10:05 pm

1 stop6h 45m

Chicago O'Hare Intl

Mon 9/14

9:15 am-11:52 am

Nonstop2h 37m

$584

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 11/18

7:00 am-2:37 pm

1 stop7h 37m

Chicago O'Hare Intl

Sun 11/22

11:45 am-6:10 pm

2 stops30h 25m

$585

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

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 $353). 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 August 13, 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?

Airfare is below average for this route at the moment.

Winnipeg to Chicago O'Hare Intl Airport flights typically cost between $509 and $692 in September.
The cheapest round-trip price found within the last 5 days was $258 on WestJet (Sep 18-Sep 21).

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 13, 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
10,114 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.7

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
United Airlines
7.4
Good
10,114 reviews
United Airlines
7.4
Good
10,114 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.7

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!

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 7h 28m. Air Canada provides one of the quickest options available for as low as $496. 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 $335. You may be able to fly from Winnipeg to Chicago O'Hare Intl Airport for 43% 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: Air Canada (84%), Air New Zealand (84%), SkyWest Airlines (83%).

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

    On average you can expect to pay $1,013 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $243 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $390.

  • 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 $353). 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
Naperville
Lake Geneva
Oak Brook
Oakbrook Terrace
Delavan
South Holland
Libertyville
Gurnee
Orland Park
Hoffman Estates
Beloit
Rockford
Aurora
Racine
Great Lakes
Janesville
Joliet

Browse thousands of different options on Cheapflights for your next trip

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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 August 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$335Average$657FlexibilityNo cancel feeOn-time69%

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