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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 252

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
20 Feb — 27 Feb1
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 21 January 2026.

Mon 1/68:30 a.m.
YWG
-
ORD
1 stop8h 13m
WestJet
Thu 4/65:30 p.m.
ORD
-
YWG
1 stop24h 10m
WestJet
Deal found 20/1C$ 408
Sat 25/46:55 p.m.
YWG
-
ORD
1 stop21h 48m
WestJet
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop29h 30m
WestJet
Deal found 19/1C$ 459
Fri 17/46:15 a.m.
YWG
-
ORD
1 stop7h 20m
Multiple Airlines
Tue 21/45:32 p.m.
ORD
-
YWG
2 stops25h 53m
Multiple Airlines
Deal found 19/1C$ 462
Mon 8/66:30 a.m.
YWG
-
ORD
1 stop10h 13m
WestJet
Thu 11/65:30 p.m.
ORD
-
YWG
1 stop18h 10m
WestJet
Deal found 19/1C$ 478
Thu 5/39:00 p.m.
YWG
-
ORD
1 stop16h 35m
Multiple Airlines
Thu 12/37:00 a.m.
ORD
-
YWG
2 stops16h 35m
Multiple Airlines
Deal found 19/1C$ 492

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 21 January 2026.

Round-trip from

C$ 408

One-way from

C$ 252

Popular in

December

Cheapest in

September

Average price

C$ 712

Good round-trip deal

C$ 660 or less

Good one-way deal

C$ 281 or less
WestJet
  • WestJet
  • 1/6-4/6
  • 2 total stops
  • 32h 23m total
  • Winnipeg to Chicago
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10/2
  • 10/2
  • 1 total stop
  • 13h 44m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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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 21 January 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

Winnipeg

Fly to

O'Hare Intl

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 1/6

7:00 a.m.-4:43 p.m.

2 stops9h 43m

Chicago O'Hare Intl

Thu 4/6

5:30 p.m.-11:25 a.m.

2 stops17h 55m

C$ 436

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

6:55 p.m.-4:43 p.m.

1 stop21h 48m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-10:00 a.m.

1 stop16h 30m

C$ 462

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 17/4

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

1 stop7h 20m

Chicago O'Hare Intl

Tue 21/4

5:15 a.m.-12:39 a.m.

2 stops19h 24m

C$ 481

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 26/2

7:30 a.m.-5:24 p.m.

1 stop9h 54m

Chicago O'Hare Intl

Sun 1/3

7:35 a.m.-7:09 p.m.

2 stops35h 34m

C$ 513

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 17/2

8:00 a.m.-3:52 p.m.

1 stop31h 52m

Chicago O'Hare Intl

Tue 24/2

12:44 p.m.-11:32 a.m.

2 stops22h 48m

C$ 535

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 24/6

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

1 stop8h 13m

Chicago O'Hare Intl

Thu 9/7

5:30 p.m.-8:20 p.m.

1 stop26h 50m

C$ 545

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 7/3

6:45 a.m.-11:38 p.m.

2 stops16h 53m

Chicago O'Hare Intl

Sat 14/3

4:20 p.m.-3:09 p.m.

1 stop22h 49m

C$ 588

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 16/2

8:00 a.m.-11:22 a.m.

1 stop27h 22m

Chicago O'Hare Intl

Mon 23/2

7:19 p.m.-11:32 a.m.

2 stops16h 13m

C$ 607

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/7

7:00 a.m.-4:48 p.m.

2 stops9h 48m

Chicago O'Hare Intl

Sat 11/7

6:00 a.m.-8:09 p.m.

1 stop14h 09m

C$ 624

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 10/2

8:00 a.m.-9:44 p.m.

1 stop13h 44m

C$ 252

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

Showing 1-10 of 16 results
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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$ 200). Flying from Winnipeg to Chicago O'Hare Intl Airport in January is currently the most expensive (average of C$ 712). 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 21 January 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.

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 21 January 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
9,188 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

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
9,188 reviews
United Airlines
7.4
Good
9,188 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

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
3,247 reviews
United Airlines
7.4
Good
9,188 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

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
10,644 reviews
United Airlines
7.4
Good
9,188 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

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.

  • 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 9h 43m. WestJet provides one of the quickest options available for as low as C$ 436. The distance between Winnipeg and Chicago O'Hare Intl Airport is about 1136 km.

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

    WestJet, at C$ 200, 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 69% 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 (77%), Air Canada (77%) or Avianca (77%) 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$ 784, our data shows the cheapest flight currently is C$ 180. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 481 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$ 200). Flying from Winnipeg to Chicago O'Hare Intl Airport in January is currently the most expensive (average of C$ 712). 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
Skokie
Downers Grove
Elk Grove Village
Racine
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 21 January 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 200AverageC$ 411FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 361AverageC$ 732FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 486AverageC$ 650FlexibilityNo 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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