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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 197

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Winnipeg to Chicago O'Hare Intl are usually found in August or October, booked 21 days in advance, depart on a Wednesday or Friday and return on a Tuesday

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 11 September 2025.

Round-trip from

C$ 327

One-way from

C$ 197

Popular in

September

Cheapest in

August

Average price

C$ 726

Good round-trip deal

C$ 546 or less

Good one-way deal

C$ 587 or less
WestJet
  • WestJet
  • 3/10-5/10
  • 2 total stops
  • 33h 55m total
  • Winnipeg to Chicago
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WestJet
  • WestJet
  • 11/10
  • 2 total stops
  • 24h 13m total
  • Winnipeg to Chicago
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High demand for flights, 4% potential price rise
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Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Winnipeg to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Winnipeg to Chicago O'Hare Intl.
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Find flight deals from Winnipeg to O'Hare Intl

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 11 September 2025.

Fri 3/106:15 p.m.YWG - ORD
1 stop18h 24mWestJet
Sun 5/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 9/9C$ 327
Sat 25/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Sun 26/102:20 p.m.ORD - YWG
1 stop29h 46mWestJet
Deal found 10/9C$ 328
Wed 1/1011:20 a.m.YWG - ORD
2 stops32h 24mMultiple Airlines
Mon 6/105:30 p.m.ORD - YWG
1 stop15h 31mMultiple Airlines
Deal found 9/9C$ 351
Sat 18/106:30 a.m.YWG - ORD
1 stop10h 13mWestJet
Thu 23/105:30 p.m.ORD - YWG
1 stop29h 40mWestJet
Deal found 10/9C$ 363
Thu 9/109:00 a.m.YWG - ORD
1 stop14h 39mMultiple Airlines
Thu 16/105:05 a.m.ORD - YWG
1 stop11h 17mMultiple Airlines
Deal found 11/9C$ 374
Sun 26/106:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
Sun 2/116:06 p.m.ORD - YWG
2 stops30h 29mMultiple Airlines
Deal found 11/9C$ 381
Thu 2/106:15 p.m.YWG - ORD
2 stops22h 28mWestJet
Sun 5/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 10/9C$ 382

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 11 September 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

Fri 3/10

6:15 p.m.-12:39 p.m.

1 stop18h 24m

Chicago O'Hare Intl

Sun 5/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 327

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/10

9:00 a.m.-11:39 p.m.

1 stop14h 39m

Chicago O'Hare Intl

Thu 16/10

5:05 a.m.-4:22 p.m.

1 stop11h 17m

C$ 374

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/10

6:15 p.m.-4:43 p.m.

2 stops22h 28m

Chicago O'Hare Intl

Sun 5/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 382

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/10

9:10 a.m.-9:58 p.m.

1 stop12h 48m

Chicago O'Hare Intl

Sun 5/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 389

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 17/10

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

2 stops24h 13m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-11:41 a.m.

1 stop18h 11m

C$ 392

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 29/9

9:00 a.m.-5:26 p.m.

1 stop8h 26m

Chicago O'Hare Intl

Tue 30/9

5:30 p.m.-2:30 p.m.

1 stop21h 00m

C$ 400

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/10

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

1 stop8h 13m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-9:09 p.m.

2 stops30h 49m

C$ 402

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/10

9:00 a.m.-11:39 p.m.

1 stop14h 39m

Chicago O'Hare Intl

Mon 13/10

5:05 a.m.-2:13 p.m.

2 stops33h 08m

C$ 450

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 18/10

6:15 p.m.-4:43 p.m.

2 stops22h 28m

Chicago O'Hare Intl

Thu 23/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 464

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 11/10

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

2 stops24h 13m

C$ 197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 19 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

How far ahead should I book a flight from Winnipeg to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to O'Hare Intl. Price data was last updated on 29 August 2025.

Booking 21 days in advance of your planned departure date is, on average, the best time to get cheap flights from Winnipeg to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 349). 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 11 September 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 27% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Winnipeg to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to O'Hare Intl. Price data was last updated on 7 September 2025.

Travelers seeking maximum savings on their Winnipeg to Chicago O'Hare Intl Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 11 September 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
8,937 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
3,091 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 7 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 18h 24m. WestJet provides one of the quickest options available for as low as C$ 327. 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 67% 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 (84%), Avianca (82%) or SkyWest Airlines (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$ 1,359, our data shows the cheapest flight currently is C$ 243. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 292 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, January is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 349). 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 200AverageC$ 460FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 362AverageC$ 604FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 488AverageC$ 630FlexibilityNo 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.

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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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