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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 140

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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
22 Jun — 29 Jun1
1 adult

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 17 June 2025.

Round-trip from

C$ 368

One-way from

C$ 140

Popular in

July

Cheapest in

May

Average price

C$ 794

Good one-way deal

C$ 342 or less
WestJet
  • WestJet
  • 5/9-10/9
  • 2 total stops
  • 29h 13m total
  • Chicago to Winnipeg
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WestJet
  • WestJet
  • 9/7
  • 1 total stop
  • 8h 16m total
  • Chicago to Winnipeg
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Highest demand for flights based on searches. 15% potential increase in price (C$ 170 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 25 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 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 17 June 2025.

Fri 5/95:30 p.m.ORD - YWG
1 stop21h 00mWestJet
Wed 10/98:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 15/6C$ 368
Wed 9/71:40 p.m.ORD - YWG
1 stop8h 16mMultiple Airlines
Fri 11/79:00 a.m.YWG - ORD
1 stop12h 30mMultiple Airlines
Deal found 15/6C$ 383
Sat 19/75:35 a.m.ORD - YWG
2 stops17h 50mDelta
Sat 26/76:45 a.m.YWG - ORD
2 stops13h 30mDelta
Deal found 17/6C$ 730
Tue 28/109:50 a.m.ORD - YWG
1 stop6h 08mAir Canada
Fri 7/115:15 a.m.YWG - ORD
1 stop5h 43mAir Canada
Deal found 16/6C$ 749
Wed 30/77:58 p.m.ORD - YWG
Nonstop2h 35mUnited Airlines
Sun 3/82:20 p.m.YWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 16/6C$ 752

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 629,999 searches. Data last updated 17 June 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 5/9

5:30 p.m.-2:30 p.m.

1 stop21h 00m

Winnipeg

Wed 10/9

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 368

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/7

1:40 p.m.-9:56 p.m.

1 stop8h 16m

Winnipeg

Fri 11/7

9:00 a.m.-9:30 p.m.

1 stop12h 30m

C$ 383

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 19/7

5:35 a.m.-11:25 p.m.

2 stops17h 50m

Winnipeg

Sat 26/7

6:45 a.m.-8:15 p.m.

2 stops13h 30m

C$ 730

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 28/10

9:50 a.m.-3:58 p.m.

1 stop6h 08m

Winnipeg

Fri 7/11

5:15 a.m.-10:58 a.m.

1 stop5h 43m

C$ 749

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 30/7

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

Winnipeg

Sun 3/8

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 752

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/7

1:40 p.m.-9:56 p.m.

1 stop8h 16m

C$ 140

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 25/9

6:00 a.m.-12:30 a.m.

2 stops18h 30m

C$ 143

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 17/7

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

C$ 342

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 10/8

8:40 a.m.-3:09 p.m.

1 stop6h 29m

C$ 349

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 27/7

6:00 a.m.-11:31 a.m.

1 stop5h 31m

C$ 362

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/6

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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of C$ 123). Flying from Chicago O'Hare Intl Airport to Winnipeg in July is currently the most expensive (average of C$ 229). 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 17 June 2025.

It’s typically best to fly out from Chicago O'Hare Intl Airport to Winnipeg in the morning. Doing so could potentially save you 42% on the flight price compared to flying at noon, which is usually more expensive.

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 17 June 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 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

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 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

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 17 June 2025.
See what other customers who have flown with Delta, United Airlines and WestJet from Chicago to Winnipeg have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,963 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
7,963 reviews
Delta
8.0
Very good
7,963 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
8,801 reviews
Delta
8.0
Very good
7,963 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
2,874 reviews
Delta
8.0
Very good
7,963 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
9,555 reviews
Delta
8.0
Very good
7,963 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago O'Hare Intl. On average, Winnipeg has 6 inbound flights from Chicago O'Hare Intl per day from 1 airline. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

  • 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 C$ 368. Other airlines that can offer you cheap pricing are Delta, from C$ 730, and Air Canada, from C$ 749. These flights start at 48% 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?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Winnipeg are WestJet (C$ 140), United Airlines (C$ 342), and Air Canada (C$ 349).

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

    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 Chicago O'Hare Intl Airport to Winnipeg on time: SkyWest Airlines (86%), Air Canada (86%), United Airlines (86%).

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

    Looking at all options, your cheapest flight can be booked for C$ 230. While the most popular route (Chicago O'Hare Intl - Winnipeg) can be booked for C$ 360 on average our data indicates C$ 342 when flying from Chicago O'Hare Intl Airport to Winnipeg.

  • 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of C$ 123). Flying from Chicago O'Hare Intl Airport to Winnipeg in July is currently the most expensive (average of C$ 229). 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

Travelling 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
Selkirk
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

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Complete your trip

Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Winnipeg car rentals
Winnipeg Airport car rentals
Brandon car rentals
Thompson car rentals

Top airline flying from O'Hare Intl to Winnipeg

Discover the top airline 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 629,999 searches. Data last updated 17 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 435AverageC$ 984FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from O'Hare Intl to Winnipeg?

Cheapflights helps you search for flights from O'Hare Intl to Winnipeg via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from O'Hare Intl to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from O'Hare Intl.

Can Cheapflights find flights from O'Hare Intl to Winnipeg with no change fees?

Certainly. Search results for flights to Winnipeg from O'Hare Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from O'Hare Intl to Winnipeg become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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