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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 152

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 25/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
11 ene. — 18 ene.1
1 adult
1 adult, Economy, 0 bags

Cheap 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 12 diciembre 2025.

mié. 10/124:35 p.m.ORD - YWG
2 stops26h 26mMultiple Airlines
dom. 14/127:30 a.m.YWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 9/12C$ 918
lun. 22/1210:37 a.m.ORD - YWG
1 stop33h 31mMultiple Airlines
lun. 5/18:00 a.m.YWG - ORD
2 stops36h 04mMultiple Airlines
Deal found 11/12C$ 975
jue. 11/125:00 a.m.ORD - YWG
2 stops14h 35mMultiple Airlines
mié. 17/124:55 p.m.YWG - ORD
1 stop27h 28mMultiple Airlines
Deal found 10/12C$ 1,063
jue. 25/129:10 a.m.ORD - YWG
Nonstop2h 47mUnited Airlines
dom. 28/122:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Deal found 10/12C$ 1,112
sáb. 27/128:30 p.m.ORD - YWG
1 stop13h 19mAir Canada
mar. 30/125:30 a.m.YWG - ORD
1 stop14h 15mAir Canada
Deal found 11/12C$ 1,157
jue. 25/128:21 p.m.ORD - YWG
2 stops29h 05mMultiple Airlines
dom. 28/125:40 p.m.YWG - ORD
1 stop8h 12mMultiple Airlines
Deal found 10/12C$ 1,214

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 12 diciembre 2025.

Round-trip from

C$ 324

One-way from

C$ 152

Popular in

July

Cheapest in

May

Average price

C$ 964
10/1-15/1
  • 10/1-15/1
  • 3 total stops
  • 48h 25m total
  • Chicago to Winnipeg
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25/1
  • 25/1
  • 3 total stops
  • 29h 24m total
  • Chicago to Winnipeg
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 136 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 31 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 629,999 searches. Data last updated 12 diciembre 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

vie. 5/6

5:30 p.m.-11:40 a.m.

1 stop18h 10m

Winnipeg

dom. 7/6

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

1 stop8h 13m

C$ 441

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 30/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

lun. 2/2

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

1 stop7h 20m

C$ 451

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

dom. 25/1

8:43 p.m.-12:41 a.m.

3 stops27h 58m

Winnipeg

dom. 1/2

8:20 p.m.-9:03 p.m.

2 stops24h 43m

C$ 488

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 25/5

5:30 p.m.-11:33 a.m.

2 stops18h 03m

Winnipeg

lun. 1/6

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

1 stop8h 13m

C$ 519

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb. 10/1

5:15 a.m.-12:41 a.m.

3 stops19h 26m

Winnipeg

jue. 15/1

12:10 p.m.-9:12 a.m.

2 stops21h 02m

C$ 539

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 23/4

7:00 a.m.-12:39 a.m.

2 stops17h 39m

Winnipeg

lun. 27/4

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

1 stop8h 13m

C$ 568

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 23/4

7:00 a.m.-12:39 a.m.

2 stops17h 39m

Winnipeg

jue. 30/4

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

1 stop8h 13m

C$ 568

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb. 24/1

6:03 a.m.-12:41 a.m.

2 stops18h 38m

C$ 156

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

dom. 25/1

2:42 p.m.-12:41 a.m.

2 stops33h 59m

C$ 160

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb. 24/1

10:00 a.m.-5:19 p.m.

1 stop7h 19m

C$ 352

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 16 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$ 123). Flying from Chicago O'Hare Intl Airport to Winnipeg in November is currently the most expensive (average of C$ 847). 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 12 diciembre 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.

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

    Departing from Chicago O'Hare Intl Airport to Winnipeg will take you 18h 10m. Chicago O'Hare Intl Airport and Winnipeg are separated by a distance of 1136 km.

  • 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 (73%), United Airlines (73%), Air Canada (70%).

  • 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$ 123). Flying from Chicago O'Hare Intl Airport to Winnipeg in November is currently the most expensive (average of C$ 847). 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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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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