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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 225

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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
25 Nov — 2 Dec1
1 adult

The best prices from Winnipeg to Chicago O'Hare Intl are usually found in January or March, booked 80 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 645,034 searches. Data last updated 20 November 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 9/12

11:35 a.m.-9:37 a.m.

2 stops22h 02m

Chicago O'Hare Intl

Tue 17/12

5:00 a.m.-7:10 p.m.

2 stops14h 10m

C$ 473

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 7/5

12:30 p.m.-4:44 p.m.

1 stop28h 14m

Chicago O'Hare Intl

Wed 14/5

5:30 p.m.-11:01 p.m.

1 stop29h 31m

C$ 480

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 31/1

7:45 a.m.-2:45 p.m.

1 stop7h 00m

Chicago O'Hare Intl

Tue 22/4

1:00 p.m.-3:24 p.m.

Nonstop2h 24m

C$ 501

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 5/4

2:15 p.m.-4:36 p.m.

Nonstop2h 21m

Chicago O'Hare Intl

Sun 13/4

7:15 a.m.-1:03 p.m.

1 stop5h 48m

C$ 584

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 13/12

12:35 p.m.-8:28 p.m.

2 stops7h 53m

Chicago O'Hare Intl

Sun 15/12

6:20 a.m.-11:45 a.m.

1 stop5h 25m

C$ 658

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/1

7:30 a.m.-10:30 p.m.

1 stop15h 00m

C$ 225

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 29/1

7:45 a.m.-2:45 p.m.

1 stop7h 00m

C$ 284

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 14/1

6:55 a.m.-11:59 p.m.

2 stops17h 04m

C$ 298

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/1

2:15 p.m.-4:51 p.m.

Nonstop2h 36m

C$ 319

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 29/1

6:00 a.m.-9:58 p.m.

2 stops15h 58m

C$ 391

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/11

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 20 November 2024.

Round-trip from

C$ 473

One-way from

C$ 225

Popular in

May

Cheapest in

January
9/12-17/12
  • 9/12-17/12
  • 4 total stops
  • 36h 12m total
  • Winnipeg to Chicago
Search Deals
10/1
  • 10/1
  • 1 total stop
  • 15h 00m total
  • Winnipeg to Chicago
Search Deals
High demand for flights, 26% potential price rise
Search Deals
Best time to find cheap flights, 22% potential price drop
Search Deals

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 20 November 2024.

Mon 9/1211:35 a.m.YWG - ORD
2 stops22h 02mMultiple Airlines
Tue 17/125:00 a.m.ORD - YWG
2 stops14h 10mMultiple Airlines
Deal found 19/11C$ 473
Wed 18/127:30 a.m.YWG - ORD
1 stop7h 21mAir Canada
Wed 25/1212:56 p.m.ORD - YWG
Nonstop2h 32mAir Canada
Deal found 19/11C$ 595
Wed 18/122:15 p.m.YWG - ORD
Nonstop2h 30mUnited Airlines
Wed 25/1212:56 p.m.ORD - YWG
Nonstop2h 32mUnited Airlines
Deal found 19/11C$ 602
Fri 13/1212:35 p.m.YWG - ORD
2 stops7h 53mDelta
Sun 15/126:20 a.m.ORD - YWG
1 stop5h 25mDelta
Deal found 19/11C$ 658
Fri 6/128:00 p.m.YWG - ORD
2 stops14h 46mWestJet
Tue 10/126:20 a.m.ORD - YWG
2 stops12h 50mWestJet
Deal found 19/11C$ 743
Fri 6/128:00 p.m.YWG - ORD
2 stops27h 14mAeromexico
Mon 9/121:00 a.m.ORD - YWG
2 stops34h 25mAeromexico
Deal found 19/11C$ 2,780

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 15 November 2024.

Booking 80 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 May is currently the most expensive (average of C$ 342). 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 20 November 2024.

It’s typically best to fly out from Winnipeg to Chicago O'Hare Intl Airport at noon. Doing so could potentially save you 28% 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 18 November 2024.

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 20 November 2024.

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 20 November 2024.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as WestJet, Air Canada and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,756 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 10

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

Delta
8.0
Very good
8,756 reviews
Delta
8.0
Very good
8,756 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 10

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

United Airlines
7.4
Good
9,171 reviews
Delta
8.0
Very good
8,756 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 10

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

WestJet
7.3
Good
2,811 reviews
Delta
8.0
Very good
8,756 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 10

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

Air Canada
7.0
Good
8,237 reviews
Delta
8.0
Very good
8,756 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 10

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$ 480, 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 33% 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 Air Canada, which is currently one of the cheapest options available, starting at C$ 284. Delta flights start at C$ 298 while deals on United Airlines start at C$ 319 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 (87%), United Airlines (87%) or Air Canada (87%) 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$ 706, our data shows the cheapest flight currently is C$ 282. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 412 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 May is currently the most expensive (average of C$ 342). 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 645,034 searches. Data last updated 20 November 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 395AverageC$ 673FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 485AverageC$ 591FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 515AverageC$ 972FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 552AverageC$ 734FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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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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