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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 158

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.
YWG — ORD
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 27 October 2025.

Wed 10/127:30 a.m.YWG - ORD
1 stop11h 16mMultiple Airlines
Wed 17/128:00 a.m.ORD - YWG
2 stops16h 41mMultiple Airlines
Deal found 26/10C$ 256
Fri 31/107:30 a.m.YWG - ORD
1 stop16h 09mMultiple Airlines
Fri 7/115:11 a.m.ORD - YWG
1 stop9h 56mMultiple Airlines
Deal found 26/10C$ 337
Fri 28/117:30 a.m.YWG - ORD
1 stop16h 38mMultiple Airlines
Tue 2/1210:00 a.m.ORD - YWG
1 stop29h 07mMultiple Airlines
Deal found 25/10C$ 339
Mon 3/119:00 p.m.YWG - ORD
2 stops14h 14mMultiple Airlines
Sat 8/115:45 p.m.ORD - YWG
1 stop21h 22mMultiple Airlines
Deal found 26/10C$ 353
Sun 2/117:30 a.m.YWG - ORD
1 stop27h 11mMultiple Airlines
Sat 8/115:45 p.m.ORD - YWG
1 stop21h 22mMultiple Airlines
Deal found 26/10C$ 368
Mon 3/119:00 p.m.YWG - ORD
2 stops14h 14mMultiple Airlines
Fri 7/115:11 a.m.ORD - YWG
1 stop9h 56mMultiple Airlines
Deal found 26/10C$ 382
Fri 31/107:30 a.m.YWG - ORD
1 stop16h 09mMultiple Airlines
Sun 2/115:11 a.m.ORD - YWG
1 stop9h 56mMultiple Airlines
Deal found 25/10C$ 388
Tue 25/115:55 a.m.YWG - ORD
2 stops14h 33mMultiple Airlines
Tue 2/124:22 p.m.ORD - YWG
1 stop22h 45mMultiple Airlines
Deal found 26/10C$ 395
Sun 2/117:30 a.m.YWG - ORD
1 stop27h 11mMultiple Airlines
Tue 4/112:31 p.m.ORD - YWG
2 stops24h 36mMultiple Airlines
Deal found 26/10C$ 407
Tue 11/119:00 p.m.YWG - ORD
3 stops27h 27mMultiple Airlines
Tue 18/1110:52 a.m.ORD - YWG
3 stops31h 14mMultiple Airlines
Deal found 25/10C$ 425

Cheap 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 27 October 2025.

Round-trip from

C$ 256

One-way from

C$ 158

Popular in

November

Cheapest in

September

Average price

C$ 709

Good round-trip deal

C$ 614 or less

Good one-way deal

C$ 282 or less
10/12-17/12
  • 10/12-17/12
  • 3 total stops
  • 27h 57m total
  • Winnipeg to Chicago
Search Deals
10/12
  • 10/12
  • 1 total stop
  • 11h 16m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 272 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 70 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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.
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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 27 October 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago O'Hare Intl Airport that are best for you.

Fly from

Winnipeg

Fly to

O'Hare Intl

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 10/12

7:30 a.m.-6:46 p.m.

1 stop11h 16m

Chicago O'Hare Intl

Wed 17/12

8:00 a.m.-12:41 a.m.

2 stops16h 41m

C$ 256

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 28/11

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

1 stop16h 38m

Chicago O'Hare Intl

Tue 2/12

10:00 a.m.-3:07 p.m.

1 stop29h 07m

C$ 339

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 25/11

5:55 a.m.-8:28 p.m.

2 stops14h 33m

Chicago O'Hare Intl

Tue 2/12

4:22 p.m.-3:07 p.m.

1 stop22h 45m

C$ 395

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 11/11

9:00 p.m.-12:27 a.m.

3 stops27h 27m

Chicago O'Hare Intl

Tue 18/11

10:52 a.m.-6:06 p.m.

3 stops31h 14m

C$ 425

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/11

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

2 stops24h 13m

Chicago O'Hare Intl

Fri 28/11

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

1 stop8h 21m

C$ 430

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 26/11

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

1 stop16h 38m

Chicago O'Hare Intl

Sat 29/11

6:48 a.m.-11:35 a.m.

2 stops28h 47m

C$ 479

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/11

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

1 stop16h 38m

Chicago O'Hare Intl

Sun 23/11

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

1 stop9h 07m

C$ 484

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/11

5:00 a.m.-6:26 p.m.

2 stops13h 26m

Chicago O'Hare Intl

Fri 28/11

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

1 stop8h 21m

C$ 501

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 23/11

7:30 a.m.-5:59 p.m.

2 stops34h 29m

Chicago O'Hare Intl

Sun 30/11

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

1 stop9h 07m

C$ 502

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 10/12

7:30 a.m.-6:46 p.m.

1 stop11h 16m

C$ 158

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

Showing 1-10 of 19 results
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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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 203). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 556). 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 27 October 2025.

It’s typically best to fly out from Winnipeg to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 26% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

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 27 October 2025.
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
8,997 reviews
Check prices

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

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
8,997 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

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
3,148 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

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
10,370 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

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 4 flights from Winnipeg to Chicago O'Hare Intl per day from 3 different airlines.

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

    WestJet, at C$ 202, 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 70% 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 SkyWest Airlines (85%), Air Canada (85%) or United Airlines (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$ 894, our data shows the cheapest flight currently is C$ 196. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 256 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 203). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 556). 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
Evanston
Des Plaines
Elk Grove Village
Skokie
Downers Grove
Naperville
Bolingbrook
Romeoville

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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 27 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 202AverageC$ 464FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 366AverageC$ 636FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 492AverageC$ 640FlexibilityNo 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?

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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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