O'Hare Intl

$122+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Jul 8 — Jul 151
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Cheapflights Tip: The best prices from Winnipeg to Chicago O'Hare Intl are usually found in August or May, booked 21 days in advance, depart on a Wednesday or Friday and return on a Friday

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 July 3, 2025.

Round-trip from

$224
(FlightHub)

One-way from

$122
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$467

Good round-trip deal

$339 or less

Good one-way deal

$213 or less
From Winnipeg to Chicago O'Hare Intl
One-way flight from Winnipeg to Chicago O'Hare Intl
Highest demand for flights based on searches. 7% potential increase in price ($36 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Winnipeg to Chicago O'Hare Intl.
Price to beat on a one-way flight from Winnipeg to Chicago O'Hare Intl.

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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:30 amYWG - ORD
1 stop8h 13mWestJet
Tue 9/235:30 pmORD - YWG
1 stop28h 00mWestJet
Deal found 7/2$224
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Mon 10/205:10 amORD - YWG
1 stop11h 12mMultiple Airlines
Deal found 7/2$228
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 9/52:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Fri 10/175:01 amORD - YWG
1 stop8h 08mUnited Airlines
Deal found 7/1$348
This Air Canada deal was found by Cheapflights users on 7/2. 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.
Sat 8/1612:00 pmYWG - ORD
1 stop8h 16mAir Canada
Sat 8/2310:40 amORD - YWG
1 stop8h 19mAir Canada
Deal found 7/2$372

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 2,558,603 searches. Data last updated July 3, 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 9/19

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Tue 9/23

5:30 pm-9:30 pm

1 stop28h 00m

$224

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/16

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Mon 10/20

5:10 am-4:22 pm

1 stop11h 12m

$228

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/5

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Fri 10/17

5:01 am-1:09 pm

1 stop8h 08m

$348

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 8/16

12:00 pm-8:16 pm

1 stop8h 16m

Chicago O'Hare Intl

Sat 8/23

10:40 am-6:59 pm

1 stop8h 19m

$372

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/3

8:30 am-4:43 pm

1 stop8h 13m

$122

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 11/11

7:30 am-10:28 pm

1 stop14h 58m

$152

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 7/15

2:20 pm-4:51 pm

Nonstop2h 31m

$206

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 7/16

5:00 am-1:13 pm

1 stop8h 13m

$218

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 7/19

6:45 am-12:50 pm

2 stops6h 05m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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.

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 June 27, 2025.

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 21 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, August is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $245). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 July 3, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 3% on flights from Winnipeg to Chicago O'Hare Intl Airport by exploring options for tickets at noon.

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 July 3, 2025.

The most flights from YWG to ORD are scheduled on a Monday (8 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 on average).

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 July 3, 2025.
See what other customers who have flown with Delta, United Airlines, and WestJet from Winnipeg to Chicago O'Hare Intl Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good
8.0
Very good

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 7 outbound flights to Chicago O'Hare Intl per day. 2 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 $224. Other airlines that can offer you cheap pricing are United Airlines, from $348, and Air Canada, from $372. You may be able to fly from Winnipeg to Chicago O'Hare Intl Airport for 51% 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?

    $122 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Air Canada, with prices starting from $206 and $218, 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: Avianca (95%), Copa Airlines (93%), Air Canada (92%).

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

    On average you can expect to pay $449 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $158 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $228.

  • 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, August is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $245). Flying from Winnipeg to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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

Traveling to a place near Winnipeg?

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Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Winnipeg to O'Hare Intl

Discover the top 2 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$222Average$550FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$443Average$729FlexibilityNo cancel feeOn-time69%

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