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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 189

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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to O'Hare Intl

Enter your travel dates to find the best prices.

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 12 December 2025.

Mon 15/128:00 a.m.YWG - ORD
1 stop12h 01mMultiple Airlines
Wed 31/1210:37 a.m.ORD - YWG
2 stops21h 58mMultiple Airlines
Deal found 9/12C$ 757
Mon 15/128:00 a.m.YWG - ORD
1 stop12h 01mMultiple Airlines
Mon 29/127:38 p.m.ORD - YWG
2 stops26h 46mMultiple Airlines
Deal found 9/12C$ 804
Fri 12/127:30 a.m.YWG - ORD
1 stop7h 10mMultiple Airlines
Wed 31/126:05 a.m.ORD - YWG
1 stop9h 02mMultiple Airlines
Deal found 9/12C$ 822
Mon 15/128:00 a.m.YWG - ORD
1 stop12h 01mMultiple Airlines
Fri 2/112:09 p.m.ORD - YWG
1 stop13h 17mMultiple Airlines
Deal found 9/12C$ 855
Wed 17/127:30 a.m.YWG - ORD
2 stops12h 31mMultiple Airlines
Wed 31/126:05 a.m.ORD - YWG
1 stop9h 02mMultiple Airlines
Deal found 9/12C$ 877
Fri 12/127:30 a.m.YWG - ORD
1 stop7h 10mMultiple Airlines
Mon 29/127:38 p.m.ORD - YWG
2 stops26h 46mMultiple Airlines
Deal found 9/12C$ 887
Wed 17/125:45 p.m.YWG - ORD
1 stop17h 55mWestJet
Tue 30/1210:00 a.m.ORD - YWG
1 stop29h 07mWestJet
Deal found 9/12C$ 902
Mon 15/128:00 a.m.YWG - ORD
1 stop12h 01mMultiple Airlines
Thu 1/111:59 p.m.ORD - YWG
2 stops21h 42mMultiple Airlines
Deal found 9/12C$ 912
Tue 16/126:00 a.m.YWG - ORD
1 stop10h 44mAir Canada
Wed 31/129:10 a.m.ORD - YWG
Nonstop2h 47mAir Canada
Deal found 9/12C$ 918

Find 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 12 December 2025.

Round-trip from

C$ 336

One-way from

C$ 189

Popular in

March

Cheapest in

September

Average price

C$ 797

Good round-trip deal

C$ 747 or less

Good one-way deal

C$ 331 or less
WestJet
  • WestJet
  • 23/1-20/3
  • 2 total stops
  • 15h 40m total
  • Winnipeg to Chicago
Search Deals
WestJet
  • WestJet
  • 12/1
  • 1 total stop
  • 7h 20m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Winnipeg to Chicago O'Hare Intl.
Search Deals

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 12 December 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 20/2

4:10 p.m.-4:53 p.m.

2 stops24h 43m

Chicago O'Hare Intl

Sat 7/3

4:51 p.m.-2:09 p.m.

1 stop21h 18m

C$ 361

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 26/2

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 419

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 21/2

11:53 a.m.-6:01 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 552

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 20/2

6:45 a.m.-6:01 p.m.

2 stops11h 16m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 563

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 22/2

5:00 a.m.-8:44 p.m.

2 stops15h 44m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 571

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 26/2

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Wed 11/3

6:15 a.m.-12:03 p.m.

1 stop5h 48m

C$ 597

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 26/2

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Tue 10/3

8:55 a.m.-4:55 p.m.

1 stop8h 00m

C$ 597

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 22/2

4:10 p.m.-1:35 p.m.

1 stop21h 25m

Chicago O'Hare Intl

Wed 11/3

12:00 p.m.-12:35 a.m.

2 stops12h 35m

C$ 616

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 22/1

6:55 p.m.-1:35 p.m.

1 stop18h 40m

Chicago O'Hare Intl

Tue 24/3

7:10 a.m.-12:35 a.m.

2 stops17h 25m

C$ 618

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 21/2

11:53 a.m.-6:01 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Sat 7/3

6:15 a.m.-11:01 a.m.

1 stop4h 46m

C$ 619

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 21 results
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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

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

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 200). Flying from Winnipeg to Chicago O'Hare Intl Airport in January is currently the most expensive (average of C$ 643). 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 12 December 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 26% on the flight price compared to flying in the afternoon, which is usually more expensive.

How much does it cost to fly round-trip from Winnipeg to Chicago O'Hare Intl Airport?

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 12 December 2025.
Read reviews from past customers who have flown United Airlines,WestJet, andAir Canada from Winnipeg to Chicago O'Hare Intl Airport. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,095 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,195 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,516 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 4 flights from Winnipeg to Chicago O'Hare Intl per day from 3 different airlines.

  • How long is the flight from Winnipeg to Chicago O'Hare Intl Airport?

    A quick flight from Winnipeg to Chicago O'Hare Intl Airport can take about 16h 35m. WestJet provides one of the quickest options available for as low as C$ 419. The distance between Winnipeg and Chicago O'Hare Intl Airport is about 1136 km.

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

    WestJet, at C$ 199, 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 69% lower than the current average price of a flight leaving 3 months from now.

  • 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 Avianca (82%), SkyWest Airlines (80%) or Air Canada (80%) 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$ 848, our data shows the cheapest flight currently is C$ 311. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 359 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 200). Flying from Winnipeg to Chicago O'Hare Intl Airport in January is currently the most expensive (average of C$ 643). 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

Travelling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Evanston
Des Plaines
Skokie
Elk Grove Village
Downers Grove
Racine
Naperville
Bolingbrook
Romeoville

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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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 199AverageC$ 410FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 485AverageC$ 643FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 495AverageC$ 727FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to O'Hare Intl?

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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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