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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 154

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
20 Apr — 27 Apr1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Chicago O'Hare Intl are usually found in January or February, booked 83 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 15 April 2025.

Round-trip from

C$ 263

One-way from

C$ 154

Popular in

May

Cheapest in

January

Average price

C$ 668

Good round-trip deal

C$ 570 or less

Good one-way deal

C$ 293 or less
WestJet
  • WestJet
  • 10/6-17/6
  • 2 total stops
  • 23h 45m total
  • Winnipeg to Chicago
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WestJet
  • WestJet
  • 1/5
  • 1 total stop
  • 8h 14m total
  • Winnipeg to Chicago
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Highest demand for flights based on searches. 12% potential increase in price (C$ 138 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 33 potential savings vs. average RT price).
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Average for round-trip flights in April 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 15 April 2025.

Tue 10/68:30 a.m.YWG - ORD
1 stop8h 14mWestJet
Tue 17/65:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 15/4C$ 263
Fri 23/512:15 p.m.YWG - ORD
2 stops23h 21mMultiple Airlines
Sun 25/56:59 p.m.ORD - YWG
2 stops29h 35mMultiple Airlines
Deal found 14/4C$ 374
Fri 23/52:20 p.m.YWG - ORD
Nonstop2h 31mAir Canada
Sun 25/51:02 p.m.ORD - YWG
Nonstop2h 29mAir Canada
Deal found 13/4C$ 551
Fri 23/52:20 p.m.YWG - ORD
Nonstop2h 31mUnited Airlines
Sun 25/57:58 p.m.ORD - YWG
Nonstop2h 35mUnited Airlines
Deal found 15/4C$ 580
Thu 15/512:52 p.m.YWG - ORD
1 stop3h 53mDelta
Mon 19/57:25 p.m.ORD - YWG
2 stops16h 32mDelta
Deal found 14/4C$ 585

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 15 April 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

Tue 10/6

8:30 a.m.-4:44 p.m.

1 stop8h 14m

Chicago O'Hare Intl

Tue 17/6

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

1 stop15h 31m

C$ 263

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 23/5

12:15 p.m.-11:36 a.m.

2 stops23h 21m

Chicago O'Hare Intl

Sun 25/5

6:59 p.m.-12:34 a.m.

2 stops29h 35m

C$ 374

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 23/5

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 25/5

1:02 p.m.-3:31 p.m.

Nonstop2h 29m

C$ 551

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 23/5

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 25/5

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

C$ 580

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 15/5

12:52 p.m.-4:45 p.m.

1 stop3h 53m

Chicago O'Hare Intl

Mon 19/5

7:25 p.m.-11:57 a.m.

2 stops16h 32m

C$ 585

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/5

8:30 a.m.-4:44 p.m.

1 stop8h 14m

C$ 154

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 6/5

9:00 a.m.-4:41 p.m.

1 stop7h 41m

C$ 216

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 12/7

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 325

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 12/7

12:40 p.m.-9:09 p.m.

2 stops8h 29m

C$ 333

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 13/7

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

C$ 743

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/4

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 11 April 2025.

Booking 82 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 15 April 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 30 March 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.

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 15 April 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 15 April 2025.
Delta
8.0
Very good
7,918 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
7,918 reviews
Delta
8.0
Very good
7,918 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
8,658 reviews
Delta
8.0
Very good
7,918 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
2,805 reviews
Delta
8.0
Very good
7,918 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
9,127 reviews
Delta
8.0
Very good
7,918 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

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 3 different airlines.

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

    WestJet, at C$ 263, 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 62% 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$ 154. Air Canada flights start at C$ 325 while deals on Delta start at C$ 333 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 (78%), Air Canada (78%) or United Airlines (78%) 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$ 591, our data shows the cheapest flight currently is C$ 156. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 338 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 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 15 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 408AverageC$ 963FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 470AverageC$ 673FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 547AverageC$ 727FlexibilityNo 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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