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O'Hare Intl

$152+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Chicago O'Hare Intl are usually found in May or January, 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 June 12, 2025.

Round-trip from

$240
(Trip.com)

One-way from

$152
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$500

Good round-trip deal

$340 or less

Good one-way deal

$227 or less
From Winnipeg to Chicago O'Hare Intl
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One-way flight from Winnipeg to Chicago O'Hare Intl
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Highest demand for flights based on searches. 5% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:30 amYWG - ORD
1 stop8h 13mWestJet
Sun 10/51:40 pmORD - YWG
1 stop7h 45mWestJet
Deal found 6/10$240
This Mytrip deal was found by Cheapflights users on 6/9. 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 6/239:00 amYWG - ORD
1 stop24h 38mMultiple Airlines
Mon 6/3010:43 amORD - YWG
2 stops32h 41mMultiple Airlines
Deal found 6/9$304
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 8/282:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Tue 9/27:15 amORD - YWG
1 stop5h 54mUnited Airlines
Deal found 6/10$453
This Air Canada deal was found by Cheapflights users on 6/12. 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.
Wed 8/65:00 amYWG - ORD
1 stop8h 13mAir Canada
Sun 8/109:55 amORD - YWG
1 stop6h 23mAir Canada
Deal found 6/12$467
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/28:35 amYWG - ORD
1 stop8h 15mDelta
Sat 8/96:00 amORD - YWG
1 stop5h 31mDelta
Deal found 6/10$482

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 June 12, 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 10/3

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/5

1:40 pm-9:25 pm

1 stop7h 45m

$240

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 6/23

9:00 am-9:38 am

1 stop24h 38m

Chicago O'Hare Intl

Mon 6/30

10:43 am-7:24 pm

2 stops32h 41m

$304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 8/28

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Tue 9/2

7:15 am-1:09 pm

1 stop5h 54m

$453

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 8/6

5:00 am-1:13 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 8/10

9:55 am-4:18 pm

1 stop6h 23m

$467

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 8/2

8:35 am-4:50 pm

1 stop8h 15m

Chicago O'Hare Intl

Sat 8/9

6:00 am-11:31 am

1 stop5h 31m

$482

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 8/1

9:00 am-9:30 pm

1 stop12h 30m

$152

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 8/13

8:30 am-4:44 pm

1 stop8h 14m

$170

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 7/12

2:20 pm-4:51 pm

Nonstop2h 31m

$251

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 8/1

5:42 pm-9:34 pm

1 stop3h 52m

$257

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 7/9

5:00 am-1:13 pm

1 stop8h 13m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 9, 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 June 12, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 9% 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 June 12, 2025.

The most flights from YWG to ORD are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 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 June 12, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines and WestJet from Winnipeg to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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!
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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!
Air Canada
7.1
Good
9,531 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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 $240. Other airlines that can offer you cheap pricing are United Airlines, from $453, and Air Canada, from $467. You may be able to fly from Winnipeg to Chicago O'Hare Intl Airport for 49% 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?

    $170 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 Delta, with prices starting from $251 and $257, 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 (90%), Air Canada (89%), Air New Zealand (89%).

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

    On average you can expect to pay $465 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $169 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $293.

  • 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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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 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$572FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$443Average$562FlexibilityNo cancel feeOn-time69%

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