Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 222

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
3 Aug — 10 Aug1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Chicago O'Hare Intl are usually found in August or May, booked 40 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 29 July 2025.

Round-trip from

C$ 305

One-way from

C$ 222

Popular in

November

Cheapest in

August

Average price

C$ 610

Good round-trip deal

C$ 724 or less

Good one-way deal

C$ 406 or less
WestJet
  • WestJet
  • 18/9-23/9
  • 2 total stops
  • 32h 23m total
  • Winnipeg to Chicago
Search Deals
2/9
  • 2/9
  • 1 total stop
  • 19h 48m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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

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 29 July 2025.

Thu 18/98:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Tue 23/95:30 p.m.ORD - YWG
1 stop24h 10mWestJet
Deal found 27/7C$ 305
Fri 5/98:30 a.m.YWG - ORD
1 stop8h 13mMultiple Airlines
Mon 8/912:53 p.m.ORD - YWG
2 stops11h 20mMultiple Airlines
Deal found 26/7C$ 342
Fri 12/912:00 p.m.YWG - ORD
1 stop8h 11mAir Canada
Fri 19/910:40 a.m.ORD - YWG
1 stop8h 19mAir Canada
Deal found 29/7C$ 444
Wed 10/92:20 p.m.YWG - ORD
Nonstop2h 31mUnited Airlines
Wed 17/97:54 p.m.ORD - YWG
Nonstop2h 39mUnited Airlines
Deal found 27/7C$ 464

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 29 July 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

Thu 18/9

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Tue 23/9

5:30 p.m.-5:40 p.m.

1 stop24h 10m

C$ 305

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/9

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Mon 8/9

12:53 p.m.-12:13 a.m.

2 stops11h 20m

C$ 342

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/9

12:00 p.m.-8:11 p.m.

1 stop8h 11m

Chicago O'Hare Intl

Fri 19/9

10:40 a.m.-6:59 p.m.

1 stop8h 19m

C$ 444

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 10/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

Wed 17/9

7:54 p.m.-10:33 p.m.

Nonstop2h 39m

C$ 464

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 2/9

8:55 p.m.-4:43 p.m.

1 stop19h 48m

C$ 222

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 20/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 277

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 20/9

12:44 p.m.-10:14 p.m.

2 stops9h 30m

C$ 285

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 12/8

8:10 p.m.-9:09 a.m.

1 stop12h 59m

C$ 320

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 23/12

5:00 a.m.-7:12 p.m.

2 stops38h 12m

C$ 396

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

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 25 July 2025.

Booking 40 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 March is currently the most expensive (average of C$ 352). 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 29 July 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 27% 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 27 July 2025.

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 29 July 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).

What’s the top layover airport for flights from Winnipeg to Chicago O'Hare Intl Airport?

Share of one-stop round-trip flights from Winnipeg to Chicago O'Hare Intl Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 50% of one-stop itineraries from Winnipeg to Chicago O'Hare Intl Airport on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Chicago O'Hare Intl Airport?

Average round-trip fare for 1-stop flights from Winnipeg to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 485.

What’s the fastest layover option from Winnipeg to Chicago O'Hare Intl Airport?

Shortest average travel time for 1-stop one-way flights from Winnipeg to Chicago O'Hare Intl Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 2h 42m.

Which airport typically offers the quickest layover for flights from Winnipeg to Chicago O'Hare Intl Airport?

Average layover duration for 1-stop one-way flights from Winnipeg to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 1h 09m.

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 29 July 2025.
Read reviews from past customers who have flown Delta,United Airlines, andWestJet 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.
Delta
8.0
Very good
7,977 reviews
Check prices

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,899 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,973 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,822 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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

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

    WestJet, at C$ 305, 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 51% 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 United Airlines, which is currently one of the cheapest options available, starting at C$ 277. Delta flights start at C$ 285 while deals on Air Canada start at C$ 320 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 Avianca (93%), SkyWest Airlines (91%) or United Airlines (91%) 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$ 1,116, our data shows the cheapest flight currently is C$ 244. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 336 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 March is currently the most expensive (average of C$ 352). 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
Elk Grove Village
Evanston
Des Plaines
Skokie
Downers Grove
Naperville
Bolingbrook
Romeoville

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.

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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 198AverageC$ 408FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 376AverageC$ 591FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 508AverageC$ 679FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

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.