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$111+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$258
(Kiwi.com)

One-way from

$111
(Kiwi.com)

Popular in

July

Cheapest in

May

Average price

$575

Good round-trip deal

$552 or less

Good one-way deal

$284 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. 14% potential increase in price ($90 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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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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 June 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/810:43 amORD - YWG
2 stops13h 48mMultiple Airlines
Fri 7/119:00 amYWG - ORD
1 stop12h 30mMultiple Airlines
Deal found 6/10$258
This Trip.com deal was found by Cheapflights users on 6/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:30 pmORD - YWG
1 stop28h 00mWestJet
Mon 10/208:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 6/12$287
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2710:35 amORD - YWG
2 stops12h 57mDelta
Tue 9/306:40 amYWG - ORD
2 stops17h 13mDelta
Deal found 6/11$431
This Air Canada deal was found by Cheapflights users on 6/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:50 amORD - YWG
1 stop6h 08mAir Canada
Fri 11/75:15 amYWG - ORD
1 stop5h 43mAir Canada
Deal found 6/11$513

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 June 12, 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

Tue 7/8

10:43 am-12:31 am

2 stops13h 48m

Winnipeg

Fri 7/11

9:00 am-9:30 pm

1 stop12h 30m

$258

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/17

5:30 pm-9:30 pm

1 stop28h 00m

Winnipeg

Mon 10/20

8:30 am-4:43 pm

1 stop8h 13m

$287

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/27

10:35 am-11:32 pm

2 stops12h 57m

Winnipeg

Tue 9/30

6:40 am-11:53 pm

2 stops17h 13m

$431

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 10/28

9:50 am-3:58 pm

1 stop6h 08m

Winnipeg

Fri 11/7

5:15 am-10:58 am

1 stop5h 43m

$513

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 7/8

10:43 am-12:31 am

2 stops13h 48m

$111

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/10

1:40 pm-9:25 pm

1 stop7h 45m

$136

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 7/15

7:58 pm-10:33 pm

Nonstop2h 35m

$252

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 7/27

9:55 am-5:40 pm

1 stop7h 45m

$260

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 7/27

6:00 am-11:31 am

1 stop5h 31m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 $497). 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 June 12, 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 10% on airfare.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Winnipeg?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Winnipeg. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Winnipeg flight should consider departing on Friday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Winnipeg

Explore weekly flight availability from O'Hare Intl to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.

The most flights from ORD to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 June 12, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines and WestJet from Chicago to Winnipeg to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,537 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 $287. Other airlines that can offer you cheap pricing are Delta, from $462, and Air Canada, from $513. These flights start at 45% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Winnipeg one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at $136. United Airlines flights start at $252 while deals on Air Canada start at $260 one-way.

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

    Consider SkyWest Airlines (78%), Air Canada (78%) or United Airlines (78%) 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 $653 for a flight from Chicago O'Hare Intl Airport to Winnipeg. The cheapest flight overall is $201 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $247.

  • 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 $497). 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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$601FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$354Average$641FlexibilityNo cancel feeOn-time69%

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