HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$130+ Cheap flights from Winnipeg (YWG) to O'Hare Intl (ORD)

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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to O'Hare Intl with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 Friday or Wednesday and return on a Thursday

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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$331
(Mytrip)

One-way from

$130
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$477
Provider with most accurate pricing for Winnipeg-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Chicago O'Hare Intl flights.
Search Deals
From Winnipeg to Chicago O'Hare Intl
Search Deals
One-way flight from Winnipeg to Chicago O'Hare Intl
Search Deals
High demand for flights, 11% potential price rise
Search Deals
Best time to find cheap flights, 3% potential price drop
Search Deals
Average for round-trip flights in December 2024
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 December 18, 2024.

This Mytrip deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3011:35 amYWG - ORD
2 stops20h 12mMultiple Airlines
Sun 2/211:10 amORD - YWG
2 stops27h 58mMultiple Airlines
Deal found 12/16$499
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:55 pmYWG - ORD
1 stop15h 02mUnited Airlines
Sun 2/27:10 amORD - YWG
1 stop6h 17mUnited Airlines
Deal found 12/16$543
This Air Canada deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/302:15 pmYWG - ORD
Nonstop2h 36mAir Canada
Sun 2/27:20 amORD - YWG
1 stop9h 08mAir Canada
Deal found 12/16$671
This Justfly.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/308:00 pmYWG - ORD
2 stops37h 21mWestJet
Fri 1/35:30 pmORD - YWG
2 stops31h 05mWestJet
Deal found 12/17$809

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 2,558,603 searches. Data last updated December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 1/15

7:30 am-5:55 am

2 stops22h 25m

Chicago O'Hare Intl

Wed 1/22

3:56 pm-12:39 am

3 stops32h 43m

$331

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 1/19

7:30 am-2:51 pm

1 stop7h 21m

Chicago O'Hare Intl

Fri 1/24

10:53 am-5:18 pm

1 stop6h 25m

$369

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 1/15

5:37 pm-9:58 pm

1 stop4h 21m

Chicago O'Hare Intl

Wed 1/22

11:05 am-11:42 pm

2 stops12h 37m

$400

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 4/4

12:15 pm-6:30 pm

1 stop6h 15m

Chicago O'Hare Intl

Mon 4/7

5:00 am-1:09 pm

1 stop8h 09m

$436

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/17

5:37 pm-3:30 pm

1 stop21h 53m

Chicago O'Hare Intl

Sun 1/19

4:58 pm-7:10 pm

2 stops26h 12m

$446

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 3/25

7:30 am-4:38 pm

1 stop9h 08m

$130

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/9

7:30 am-2:51 pm

1 stop7h 21m

$209

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 3/25

11:00 am-7:58 am

2 stops20h 58m

$227

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/9

5:00 am-4:13 pm

2 stops11h 13m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Compare providers for flights from Winnipeg to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to O'Hare Intl in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Winnipeg-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 December 13, 2024.

The price you pay for your flight from Winnipeg to Chicago O'Hare Intl Airport may vary depending on when you book. For the best chance of a lower fare, look to book 80 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $232). Flying from Winnipeg to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $308). 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 December 18, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 12% on flights from Winnipeg to Chicago O'Hare Intl Airport by exploring options for tickets in the morning.

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 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 December 18, 2024.
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

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
8,604 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

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
9,059 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

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
2,818 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

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
8,382 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

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?

    For a flight from Winnipeg to Chicago O'Hare Intl, you will be flying from Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city. Winnipeg is the only Winnipeg airport and it handles 1 outbound flight to Chicago O'Hare Intl per day. 3 airlines have flights to Chicago O'Hare Intl from Winnipeg on a regular basis.

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

    Cheapflights users have booked flights from Winnipeg to Chicago O'Hare Intl Airport round-trip from $369. Other airlines that can offer you cheap pricing are Delta, from $400, and United Airlines, from $436. You may be able to fly from Winnipeg to Chicago O'Hare Intl Airport for 28% less than the average price by searching for these airlines.

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

    $209 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $227 and $298, respectively.

  • What are the most reliable airlines from Winnipeg to Chicago O'Hare Intl Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Winnipeg to Chicago O'Hare Intl Airport on time: SkyWest Airlines (84%), United Airlines (84%), Air Canada (80%).

  • What are the cheapest flights from Winnipeg to Chicago O'Hare Intl Airport?

    On average you can expect to pay $579 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $219 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $308.

  • 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, September is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $232). Flying from Winnipeg to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $308). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Midway flights

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 2,558,603 searches. Data last updated December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$289Average$550FlexibilityNo cancel feeOn-time67%
DeltaCheapest$370Average$671FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$441Average$533FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.