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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 280

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 27/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
23 Aug — 30 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to O'Hare Intl

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to O'Hare Intl
Explore the most affordable flight options available from Winnipeg to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 July 2026.

Thu 15/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 18/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 22/7C$ 390
Sat 5/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 11/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 24/7C$ 418
Fri 18/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 25/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 23/7C$ 424
Fri 25/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 27/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 23/7C$ 431
Sat 5/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 10/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 22/7C$ 444
Sat 5/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Fri 11/97:45 a.m.
ORD
-
YWG
2 stops17h 10m
Multiple Airlines
Deal found 22/7C$ 487
Thu 27/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Mon 31/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 22/7C$ 500
Fri 4/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 13/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 22/7C$ 507
Fri 21/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 28/85:30 p.m.
ORD
-
YWG
1 stop26h 45m
WestJet
Deal found 24/7C$ 513
Tue 22/97:00 a.m.
YWG
-
ORD
2 stops9h 40m
WestJet
Fri 25/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 22/7C$ 525

Find flight deals from Winnipeg to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to O'Hare Intl (ORD). 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 24 July 2026.

Round-trip from

C$ 390

One-way from

C$ 280

Popular in

October

Cheapest in

September

Average price

C$ 748

Good round-trip deal

C$ 674 or less

Good one-way deal

C$ 760 or less
WestJet
  • WestJet
  • 15/10-18/10
  • 2 total stops
  • 17h 05m total
  • Winnipeg to Chicago
Search Deals
WestJet
  • WestJet
  • 27/8
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 57 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Winnipeg to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to O'Hare Intl 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 24 July 2026.
Use the filters below to find and compare flights from Winnipeg to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 8/9

9:20 a.m.-4:19 p.m.

1 stop6h 59m

Chicago O'Hare Intl

Sun 13/9

8:03 a.m.-3:19 p.m.

1 stop7h 16m

C$ 693

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 23/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

Chicago O'Hare Intl

Sat 26/9

8:03 a.m.-3:19 p.m.

1 stop7h 16m

C$ 744

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 18/11

7:00 a.m.-2:37 p.m.

1 stop7h 37m

Chicago O'Hare Intl

Sun 22/11

11:45 a.m.-6:10 p.m.

2 stops30h 25m

C$ 821

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 18/11

2:15 p.m.-4:36 p.m.

Nonstop2h 21m

Chicago O'Hare Intl

Sun 22/11

10:50 a.m.-8:48 p.m.

1 stop9h 58m

C$ 944
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/8

2:00 p.m.-4:35 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Fri 28/8

9:15 a.m.-11:52 a.m.

Nonstop2h 37m

C$ 944

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 13/10

7:00 a.m.-9:35 a.m.

Nonstop2h 35m

Chicago O'Hare Intl

Sun 18/10

10:00 a.m.-12:37 p.m.

Nonstop2h 37m

C$ 948

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 2/9

7:00 a.m.-9:35 a.m.

Nonstop2h 35m

Chicago O'Hare Intl

Sat 5/9

9:15 a.m.-11:52 a.m.

Nonstop2h 37m

C$ 948
Cheapest one-way

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 31/8

9:05 p.m.-4:40 p.m.

1 stop19h 35m

C$ 301

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 26/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 317

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 15/9

7:00 a.m.-5:42 a.m.

3 stops22h 42m

C$ 330

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/7

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Best time to book a flight from Winnipeg to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Winnipeg 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 Winnipeg to Chicago O'Hare Intl Airport

What is the cheapest month to book a flight from Winnipeg to Chicago O'Hare Intl Airport?

Currently, September is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 520). Flying from Winnipeg to Chicago O'Hare Intl Airport in October is currently the most expensive (average of C$ 1,241). 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 YWG to ORD?

Find hourly flight availability from Winnipeg to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 24 July 2026.

When flying from Winnipeg to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Airfare is below average for this route at the moment.

Winnipeg to Chicago O'Hare Intl Airport flights typically cost between C$ 627 and C$ 844 in October.
The cheapest round-trip price found within the last 5 days was C$ 390 on WestJet (15 Oct-18 Oct).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated 24 July 2026.
Read reviews from past customers who have flown United Airlines,WestJet, andAir Canada from Winnipeg to Chicago O'Hare Intl Airport. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,034 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
10,034 reviews
United Airlines
7.4
Good
10,034 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,416 reviews
United Airlines
7.4
Good
10,034 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
11,382 reviews
United Airlines
7.4
Good
10,034 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to O'Hare Intl. 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 from for flights from Winnipeg to Chicago O'Hare Intl?

    If you book a flight to Chicago O'Hare Intl from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 8 flights from Winnipeg to Chicago O'Hare Intl per day from 3 different airlines.

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

    A quick flight from Winnipeg to Chicago O'Hare Intl Airport can take about 2h 21m. Porter Airlines provides one of the quickest options available for as low as C$ 944. The distance between Winnipeg and Chicago O'Hare Intl Airport is about 1136 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines flying from Winnipeg to Chicago O'Hare Intl Airport round-trip?

    WestJet, at C$ 276, was found to be the cheapest airline from Winnipeg to Chicago O'Hare Intl Airport.Alternate airlines to your destination round-trip include Air Canada and United Airlines. WestJet is priced at 65% lower than the current average price of a flight leaving 3 months from now.

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

    No one likes to see their flight delayed. When booking a flight from Winnipeg to Chicago O'Hare Intl Airport consider choosing Copa Airlines (87%), Avianca (85%) or Air Canada (85%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Winnipeg to Chicago O'Hare Intl Airport is generally C$ 1,052, our data shows the cheapest flight currently is C$ 317. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 431 for that flight.

  • Can I find deals for flights from Winnipeg to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Winnipeg to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to O'Hare Intl.

  • Can I find deals for business class flights from Winnipeg to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Winnipeg to O'Hare Intl 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 Winnipeg to Chicago O'Hare Intl Airport?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 520). Flying from Winnipeg to Chicago O'Hare Intl Airport in October is currently the most expensive (average of C$ 1,241). 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
Northbrook
Evanston
Des Plaines
Downers Grove
Elk Grove Village
Racine
Bolingbrook
Naperville
Schaumburg

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Winnipeg to O'Hare Intl

Discover the top 3 airlines that operate flights from Winnipeg to O'Hare Intl. 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 24 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 276AverageC$ 493FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 372AverageC$ 856FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 496AverageC$ 920FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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

When you search for this flight from Winnipeg to O'Hare Intl, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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

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 O'Hare Intl from Winnipeg.

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

Yes! Cheapflights helps users easily find flights from Winnipeg to O'Hare Intl with no change fees.

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

Not ready to book yet? You can track prices for flights from Winnipeg to O'Hare Intl on Cheapflights with our Price Alert feature and get notified when better prices are available.

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