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$53+ Cheap flights from O'Hare Intl (ORD) to Winnipeg (YWG)

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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Winnipeg (YWG). 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 14, 2025.

Round-trip from

$232
(oojo)

One-way from

$53
(Kiwi.com)

Popular in

July

Cheapest in

May

Average price

$541

Good round-trip deal

$448 or less
From Chicago O'Hare Intl to Winnipeg
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One-way flight from Chicago O'Hare Intl to Winnipeg
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Highest demand for flights based on searches. 11% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 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 Chicago O'Hare Intl to Winnipeg.
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Find flight deals from O'Hare Intl to Winnipeg

Cheapest flights from O'Hare Intl to Winnipeg
Explore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This oojo deal was found by Cheapflights users on 8/13. 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 10/175:30 pmORD - YWG
1 stop29h 40mWestJet
Mon 10/208:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 8/13$232
This oojo deal was found by Cheapflights users on 8/14. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:30 pmORD - YWG
1 stop26h 45mWestJet
Fri 10/248:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 8/14$234
This oojo deal was found by Cheapflights users on 8/13. 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 9/125:30 pmORD - YWG
1 stop26h 45mWestJet
Fri 9/194:30 pmYWG - ORD
1 stop20h 09mWestJet
Deal found 8/13$250
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:30 pmORD - YWG
2 stops17h 56mWestJet
Sun 10/196:15 pmYWG - ORD
2 stops22h 28mWestJet
Deal found 8/14$251
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Thu 9/115:30 pmORD - YWG
1 stop15h 31mMultiple Airlines
Sun 9/1410:45 amYWG - ORD
2 stops30h 41mMultiple Airlines
Deal found 8/14$252
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/271:40 pmORD - YWG
1 stop7h 45mMultiple Airlines
Sat 10/49:10 amYWG - ORD
1 stop12h 48mMultiple Airlines
Deal found 8/13$256

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Winnipeg 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 14, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Winnipeg that are best for you.

Fly from

O'Hare Intl

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/17

5:30 pm-11:10 pm

1 stop29h 40m

Winnipeg

Mon 10/20

8:30 am-4:43 pm

1 stop8h 13m

$232

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/17

5:30 pm-11:10 pm

1 stop29h 40m

Winnipeg

Sun 10/19

8:30 am-4:43 pm

1 stop8h 13m

$234

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/16

5:30 pm-9:30 pm

1 stop28h 00m

Winnipeg

Fri 10/24

8:30 am-4:43 pm

1 stop8h 13m

$234

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/12

5:30 pm-8:15 pm

1 stop26h 45m

Winnipeg

Fri 9/19

4:30 pm-12:39 pm

1 stop20h 09m

$250

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/11

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

Sun 9/14

10:45 am-5:26 pm

2 stops30h 41m

$252

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/27

1:40 pm-9:25 pm

1 stop7h 45m

Winnipeg

Sat 10/4

9:10 am-9:58 pm

1 stop12h 48m

$256

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/27

1:40 pm-9:25 pm

1 stop7h 45m

$53

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/25

5:30 pm-5:25 pm

2 stops23h 55m

$101

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 9/28

5:30 pm-9:25 pm

2 stops27h 55m

$101

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/21

2:20 pm-10:41 pm

1 stop8h 21m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 13 results
1
2

Best time to book a flight from O'Hare Intl to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from O'Hare Intl 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 Chicago O'Hare Intl Airport to Winnipeg

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

Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of $358). Flying from Chicago O'Hare Intl Airport to Winnipeg in December is currently the most expensive (average of $495). 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 ORD to YWG?

Find hourly flight availability from O'Hare Intl to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 14% on airfare.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated August 14, 2025.
Get a feel of what it's like to fly with United Airlines and Air Canada from Chicago O'Hare Intl Airport to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,916 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,916 reviews
United Airlines
7.4
Good
8,916 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Air Canada
7.1
Good
9,949 reviews
United Airlines
7.4
Good
8,916 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Winnipeg. 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 into for flights to Winnipeg from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Winnipeg, you will be flying into Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city. Winnipeg is the only Winnipeg airport and it handles 5 inbound flights from Chicago O'Hare Intl per day. 2 airlines have flights to Winnipeg from Chicago O'Hare Intl on a regular basis.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Winnipeg round-trip?

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Winnipeg round-trip from $226. Another airline that can offer you cheap pricing is United Airlines. These flights start at 57% lower than the current average price 3 months from now.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Winnipeg?

    Consider SkyWest Airlines (79%), Air Canada (79%) or United Airlines (79%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Winnipeg.

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

    On average you can expect to pay $817 for a flight from Chicago O'Hare Intl Airport to Winnipeg. The cheapest flight overall is $199 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $244.

  • Can I find deals for flights from O'Hare Intl to Winnipeg that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Winnipeg.

  • Can I find deals for business class flights from O'Hare Intl to Winnipeg?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Winnipeg 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 Chicago O'Hare Intl Airport to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of $358). Flying from Chicago O'Hare Intl Airport to Winnipeg in December is currently the most expensive (average of $495). 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Alternative routes for O'Hare Intl to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
Midway to Winnipeg flights

Top 2 airlines flying from O'Hare Intl to Winnipeg

Discover the top 2 airlines that operate flights from O'Hare Intl to Winnipeg. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$542FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$429Average$627FlexibilityNo cancel feeOn-time69%

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