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$236+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Jun 27 — Jul 41
Sat 6/27
Sat 7/4
1 adult, Economy
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Cheap 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 May 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/26. 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 10/155:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 10/187:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 5/26$400
This Kiwi.com deal was found by Cheapflights users on 5/25. 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 9/55:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 9/1211:15 am
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 5/25$427
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 9/175:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 9/2011:15 am
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 5/24$436
This Mytrip deal was found by Cheapflights users on 5/24. 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.
Thu 7/97:25 am
ORD
-
YWG
1 stop9h 00m
Multiple Airlines
Mon 7/138:10 pm
YWG
-
ORD
3 stops23h 55m
Multiple Airlines
Deal found 5/24$449
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 10/157:00 am
ORD
-
YWG
2 stops10h 58m
Multiple Airlines
Sun 10/187:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 5/26$452
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 10/157:00 am
ORD
-
YWG
2 stops10h 58m
Multiple Airlines
Mon 10/197:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 5/24$453
This oojo deal was found by Cheapflights users on 5/24. 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 10/155:30 pm
ORD
-
YWG
1 stop18h 45m
WestJet
Mon 10/197:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 5/24$478
This Trip.com deal was found by Cheapflights users on 5/26. 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.
Tue 9/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 9/77:10 pm
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 5/26$485

Find 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 May 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$400
(Kiwi.com)

One-way from

$236
(Justfly.com)

Popular in

February

Cheapest in

September

Average price

$785

Good round-trip deal

$844 or less

Good one-way deal

$804 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Winnipeg flights.
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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. 23% potential increase in price ($201 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Winnipeg.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Winnipeg.
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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 May 28, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/17

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Mon 9/21

7:00 am-4:40 pm

1 stop9h 40m

$485

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/17

7:00 am-5:58 pm

2 stops10h 58m

Winnipeg

Mon 9/21

9:20 am-4:18 pm

1 stop6h 58m

$601

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 7/8

12:27 pm-4:51 pm

1 stop4h 24m

Winnipeg

Tue 7/14

5:41 pm-9:52 pm

1 stop4h 11m

$734

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 8/29

11:26 am-9:45 am

2 stops22h 19m

Winnipeg

Mon 8/31

6:05 pm-8:17 pm

2 stops26h 12m

$763

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 8/2

8:00 pm-10:38 pm

Nonstop2h 38m

Winnipeg

Wed 8/12

7:00 am-9:35 am

Nonstop2h 35m

$865

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 8/29

7:54 pm-10:33 pm

Nonstop2h 39m

Winnipeg

Mon 8/31

7:00 am-9:35 am

Nonstop2h 35m

$865
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/15

9:15 am-11:39 am

Nonstop2h 24m

Winnipeg

Mon 10/19

7:00 am-9:21 am

Nonstop2h 21m

$865

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/28

9:15 am-11:39 am

Nonstop2h 24m

Winnipeg

Mon 11/2

2:15 pm-4:36 pm

Nonstop2h 21m

$865

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 8/6

8:00 pm-10:38 pm

Nonstop2h 38m

Winnipeg

Thu 8/13

2:00 pm-4:35 pm

Nonstop2h 35m

$865
Cheapest one-way

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 8/31

5:30 pm-12:55 am

1 stop7h 25m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/23

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Compare providers for flights from O'Hare Intl to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Winnipeg in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Winnipeg 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 Chicago O'Hare Intl Airport-Winnipeg 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 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 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 May 28, 2026.

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 in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 27% on airfare.

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

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 May 28, 2026.
Get a feel of what it's like to fly with United Airlines and WestJet 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
9,751 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,751 reviews
United Airlines
7.4
Good
9,751 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
WestJet
7.2
Good
3,347 reviews
United Airlines
7.4
Good
9,751 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 6 inbound flights from Chicago O'Hare Intl per day. 2 airlines have flights to Winnipeg from Chicago O'Hare Intl on a regular basis.

  • How long is the flight from Chicago O'Hare Intl Airport to Winnipeg?

    Airlines like WestJet, Porter Airlines, and Delta fly from Chicago O'Hare Intl Airport to Winnipeg in about 4h 24m. The time it takes to get you to your destination can typically vary by up to 6h 34m. The distance between Chicago O'Hare Intl Airport and Winnipeg is about 706 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $222. Another airline that can offer you cheap pricing is United Airlines. These flights start at 65% 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 (64%), Air Canada (64%) or United Airlines (64%) 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 $942 for a flight from Chicago O'Hare Intl Airport to Winnipeg. The cheapest flight overall is $801 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $427.

  • 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.

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 May 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$222Average$405FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$291Average$703FlexibilityNo cancel feeOn-time69%

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