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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 111

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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

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 27 October 2025.

Round-trip from

C$ 350

One-way from

C$ 111

Popular in

November

Cheapest in

May

Average price

C$ 884
20/11-1/12
  • 20/11-1/12
  • 3 total stops
  • 38h 44m total
  • Chicago to Winnipeg
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10/12
  • 10/12
  • 3 total stops
  • 28h 05m total
  • Chicago to Winnipeg
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Highest demand for flights based on searches. 18% potential increase in price (C$ 239 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from O'Hare Intl to Winnipeg

Enter your travel dates to find the best prices.

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 27 October 2025.

Thu 20/116:35 p.m.ORD - YWG
1 stop20h 32mMultiple Airlines
Mon 1/129:00 p.m.YWG - ORD
2 stops18h 12mMultiple Airlines
Deal found 26/10C$ 350
Thu 20/116:35 p.m.ORD - YWG
1 stop20h 32mMultiple Airlines
Mon 24/119:00 p.m.YWG - ORD
2 stops14h 34mMultiple Airlines
Deal found 26/10C$ 376
Mon 24/116:35 p.m.ORD - YWG
2 stops23h 31mMultiple Airlines
Mon 1/128:00 a.m.YWG - ORD
1 stop25h 17mMultiple Airlines
Deal found 26/10C$ 437
Sun 23/116:00 a.m.ORD - YWG
1 stop9h 07mMultiple Airlines
Sun 30/117:30 a.m.YWG - ORD
2 stops51h 05mMultiple Airlines
Deal found 26/10C$ 467
Thu 20/116:35 p.m.ORD - YWG
1 stop20h 32mMultiple Airlines
Sun 30/114:55 p.m.YWG - ORD
2 stops37h 30mMultiple Airlines
Deal found 26/10C$ 484
Fri 21/116:00 a.m.ORD - YWG
1 stop9h 07mMultiple Airlines
Sun 23/117:30 a.m.YWG - ORD
1 stop16h 38mMultiple Airlines
Deal found 26/10C$ 488
Tue 23/1212:32 p.m.ORD - YWG
1 stop26h 35mMultiple Airlines
Sun 28/125:40 p.m.YWG - ORD
1 stop8h 12mMultiple Airlines
Deal found 26/10C$ 521
Wed 10/129:06 p.m.ORD - YWG
3 stops27h 35mMultiple Airlines
Wed 17/127:30 a.m.YWG - ORD
2 stops16h 39mMultiple Airlines
Deal found 26/10C$ 525

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 27 October 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

Mon 24/11

6:35 p.m.-6:06 p.m.

2 stops23h 31m

Winnipeg

Mon 1/12

8:00 a.m.-9:17 a.m.

1 stop25h 17m

C$ 437

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 21/11

6:00 a.m.-3:07 p.m.

1 stop9h 07m

Winnipeg

Sun 23/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

C$ 488

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 23/12

6:05 p.m.-3:07 p.m.

2 stops21h 02m

Winnipeg

Sun 28/12

5:40 p.m.-1:52 a.m.

1 stop8h 12m

C$ 607

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/12

5:30 a.m.-3:07 p.m.

1 stop9h 37m

Winnipeg

Wed 17/12

7:30 a.m.-6:43 p.m.

1 stop11h 13m

C$ 694

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 16/12

12:09 p.m.-3:07 p.m.

3 stops26h 58m

Winnipeg

Sun 21/12

8:20 p.m.-3:21 p.m.

2 stops19h 01m

C$ 744

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 13/11

6:00 a.m.-8:06 p.m.

2 stops14h 06m

Winnipeg

Fri 14/11

6:45 a.m.-7:50 p.m.

2 stops13h 05m

C$ 786

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 28/12

6:30 p.m.-11:44 p.m.

1 stop5h 14m

Winnipeg

Mon 5/1

6:15 a.m.-1:35 p.m.

1 stop7h 20m

C$ 812

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/12

4:01 p.m.-8:06 p.m.

3 stops28h 05m

C$ 111

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 23/12

12:32 p.m.-3:07 p.m.

1 stop26h 35m

C$ 182

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 15/11

5:45 p.m.-3:07 p.m.

1 stop21h 22m

C$ 257

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

Showing 1-10 of 14 results
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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, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of C$ 127). Flying from Chicago O'Hare Intl Airport to Winnipeg in November is currently the most expensive (average of C$ 859). 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 27 October 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 52% on the flight price compared to flying in the evening, which is usually more expensive.

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 3 inbound flights from Chicago O'Hare Intl per day from 0 airlines. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

  • 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 (89%), Air Canada (89%), United Airlines (89%).

  • 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, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Winnipeg (average of C$ 127). Flying from Chicago O'Hare Intl Airport to Winnipeg in November is currently the most expensive (average of C$ 859). 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 Winnipeg?

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

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Fly with Cheapflights

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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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