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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 204

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 14/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
27 Feb — 6 Mar1
1 adult

The best prices from Winnipeg to Chicago O'Hare Intl are usually found in January or December, booked 49 days in advance, depart on a Wednesday or Tuesday 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 22 February 2025.

Round-trip from

C$ 382

One-way from

C$ 204

Popular in

May

Cheapest in

January

Average price

C$ 784

Good round-trip deal

C$ 586 or less

Good one-way deal

C$ 275 or less
WestJet
  • WestJet
  • 5/3-10/3
  • 2 total stops
  • 27h 30m total
  • Winnipeg to Chicago
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WestJet
  • WestJet
  • 14/4
  • 1 total stop
  • 9h 36m total
  • Winnipeg to Chicago
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Highest demand for flights based on searches. 11% potential increase in price (C$ 135 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 29 potential savings vs. average RT price).
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Average for round-trip flights in February 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 22 February 2025.

Wed 5/38:25 p.m.YWG - ORD
1 stop19h 31mWestJet
Mon 10/34:45 p.m.ORD - YWG
1 stop7h 59mWestJet
Deal found 21/2C$ 382
Tue 8/47:30 a.m.YWG - ORD
2 stops34h 11mMultiple Airlines
Tue 15/47:49 p.m.ORD - YWG
2 stops19h 19mMultiple Airlines
Deal found 22/2C$ 409
Fri 26/95:00 a.m.YWG - ORD
1 stop5h 53mAir Canada
Tue 30/91:00 p.m.ORD - YWG
Nonstop2h 24mAir Canada
Deal found 20/2C$ 549
Thu 27/312:53 p.m.YWG - ORD
1 stop19h 51mDelta
Mon 31/39:40 a.m.ORD - YWG
1 stop7h 13mDelta
Deal found 21/2C$ 564
Thu 17/44:25 p.m.YWG - ORD
1 stop8h 10mUnited Airlines
Mon 21/45:00 a.m.ORD - YWG
1 stop8h 09mUnited Airlines
Deal found 20/2C$ 642

Find flights from Winnipeg to O'Hare Intl within your budget

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 22 February 2025.

Fly from

Winnipeg

Fly to

O'Hare Intl

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 5/3

8:25 p.m.-3:56 p.m.

1 stop19h 31m

Chicago O'Hare Intl

Mon 10/3

4:45 p.m.-12:44 a.m.

1 stop7h 59m

C$ 382

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 8/4

7:30 a.m.-5:41 p.m.

2 stops34h 11m

Chicago O'Hare Intl

Tue 15/4

7:49 p.m.-3:08 p.m.

2 stops19h 19m

C$ 409

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 27/3

12:53 p.m.-8:44 a.m.

1 stop19h 51m

Chicago O'Hare Intl

Mon 31/3

9:40 a.m.-4:53 p.m.

1 stop7h 13m

C$ 564

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 16/7

5:00 a.m.-12:54 p.m.

1 stop7h 54m

Chicago O'Hare Intl

Wed 23/7

8:00 p.m.-10:35 p.m.

Nonstop2h 35m

C$ 596

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 17/4

4:25 p.m.-12:35 a.m.

1 stop8h 10m

Chicago O'Hare Intl

Mon 21/4

5:00 a.m.-1:09 p.m.

1 stop8h 09m

C$ 642

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 14/4

6:20 a.m.-3:56 p.m.

1 stop9h 36m

C$ 204

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 18/3

7:30 a.m.-4:37 p.m.

1 stop9h 07m

C$ 207

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 14/4

2:20 p.m.-4:48 p.m.

Nonstop2h 28m

C$ 304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 2/8

5:00 a.m.-11:37 p.m.

3 stops18h 37m

C$ 467

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

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.

Travel insights for flights from Winnipeg to O'Hare Intl

Get recent, data-driven insights about flights from Winnipeg to O'Hare Intl including ideal travel times, pricing trends, and more.

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 14 February 2025.

Booking 49 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$ 355). 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 22 February 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 29% on the flight price compared to flying in the morning, 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 16 February 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. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Winnipeg to Chicago O'Hare Intl Airport

Explore weekly flight availability from Winnipeg to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 22 February 2025.

The most flights from YWG to ORD are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 43.0 mm.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 22 February 2025.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as Delta, United Airlines and WestJet. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,212 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,212 reviews
Delta
8.0
Very good
8,212 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,759 reviews
Delta
8.0
Very good
8,212 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.2
Good
2,800 reviews
Delta
8.0
Very good
8,212 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Canada
7.0
Good
8,758 reviews
Delta
8.0
Very good
8,212 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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

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

    WestJet, at C$ 382, was found to be the cheapest airline from Winnipeg to Chicago O'Hare Intl Airport.Alternate airlines to your destination round-trip include Delta and Air Canada. WestJet is priced at 50% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Winnipeg to Chicago O'Hare Intl Airport one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 204. Air Canada flights start at C$ 304 while deals on United Airlines start at C$ 467 one-way.

  • 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 (66%), Air Canada (66%) or United Airlines (66%) 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$ 651, our data shows the cheapest flight currently is C$ 188. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 298 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$ 355). 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

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Top 4 airlines flying from Winnipeg to O'Hare Intl

Discover the top 4 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 22 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 481AverageC$ 726FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 495AverageC$ 986FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 545AverageC$ 686FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 560AverageC$ 744FlexibilityNo 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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