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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from C$ 228

YWG — ORD
5 Oct — 12 Oct1
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

Sat 7/1111:40 a.m. -
2 stops24h 00m
Fri 20/1112:20 p.m. -
1 stop12h 24m
Deal found 3/9C$ 499
Sat 7/1111:40 a.m. -
2 stops24h 00m
Sat 21/116:20 p.m. -
1 stop16h 25m
Deal found 3/9C$ 501
Sat 7/117:05 p.m. -
1 stop16h 35m
Thu 19/1112:20 p.m. -
1 stop9h 37m
Deal found 3/9C$ 505
Sat 7/117:05 p.m. -
1 stop16h 35m
Sat 21/1112:20 p.m. -
1 stop12h 24m
Deal found 3/9C$ 506
Thu 17/99:20 a.m. -
1 stop6h 58m
Mon 21/95:30 p.m. -
1 stop7h 25m
Deal found 5/9C$ 515
Sun 4/106:05 p.m. -
2 stops45h 15m
Fri 9/105:30 p.m. -
1 stop7h 25m
Deal found 4/9C$ 520
Sat 3/105:10 p.m. -
1 stop15h 50m
Sun 4/102:00 p.m. -
1 stop10h 55m
Deal found 3/9C$ 526
Fri 2/109:20 a.m. -
1 stop6h 58m
Sun 4/105:30 p.m. -
1 stop7h 25m
Deal found 1/9C$ 530
Fri 2/109:05 p.m. -
2 stops21h 18m
Fri 9/105:30 p.m. -
1 stop7h 25m
Deal found 4/9C$ 542

Find flight deals from Winnipeg to O'Hare Intl

Round-trip from

C$ 499

One-way from

C$ 228

Popular in

October

Cheapest in

February

Average price

C$ 701

Good round-trip deal

C$ 802 or less

Good one-way deal

C$ 518 or less
Porter Airlines
  • Porter Airlines
  • 7/11-19/11
  • 3 total stops
  • 33h 37m total
  • Winnipeg to Chicago
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WestJet
  • WestJet
  • 18/10-31/12
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 95 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 48 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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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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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 21/9

9:05 p.m.-4:40 p.m.

1 stop19h 35m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 274

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 17/10

9:05 p.m.-4:40 p.m.

1 stop19h 35m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 284

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 20/10

9:20 a.m.-4:14 p.m.

1 stop6h 54m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 306

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 8/11

8:35 p.m.-6:45 p.m.

2 stops22h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 311

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 18/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 311

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 6/1

7:00 a.m.-2:37 p.m.

1 stop7h 37m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 311

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 21/9

11:40 a.m.-8:20 p.m.

2 stops8h 40m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 317

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 14/11

5:00 a.m.-12:21 a.m.

3 stops19h 21m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 356

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 18/9

6:00 a.m.-11:48 a.m.

3 stops29h 48m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 378

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 3/11

5:15 a.m.-2:52 p.m.

2 stops9h 37m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 418

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 22 resultsSorted by cheapest first
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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

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, February is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 686). Flying from Winnipeg to Chicago O'Hare Intl Airport in October is currently the most expensive (average of C$ 1,219). 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?

When flying from Winnipeg to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Airfare is typical for this route at the moment.

Winnipeg to Chicago O'Hare Intl Airport flights typically cost between C$ 463 and C$ 869 in November.
The cheapest round-trip price found within the last 5 days was C$ 499 on Porter Airlines (7 Nov-19 Nov).

Reviews of airlines servicing O'Hare Intl

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
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
United Airlines
7.4
Good
10,172 reviews
United Airlines
7.4
Good
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
WestJet
7.2
Good
3,446 reviews
United Airlines
7.4
Good
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Air Canada
7.1
Good
11,592 reviews
United Airlines
7.4
Good
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!

Related info for your journey

  • 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 5 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 7h 36m. Porter Airlines provides one of the quickest options available for as low as C$ 686. 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$ 271, was found to be the cheapest airline from Winnipeg to Chicago O'Hare Intl Airport.Alternate airlines to your destination round-trip include United Airlines and Air Canada. WestJet is priced at 68% 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 Air Canada (86%), SkyWest Airlines (85%) or United Airlines (85%) 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$ 1,248, our data shows the cheapest flight currently is C$ 227. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 499 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, February is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of C$ 686). Flying from Winnipeg to Chicago O'Hare Intl Airport in October is currently the most expensive (average of C$ 1,219). 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
Northbrook
Evanston
Des Plaines
Racine
Rockford
Naperville
Schaumburg
Elk Grove Village
Skokie

Browse thousands of different options on Cheapflights for your next trip

Top 3 airlines flying from Winnipeg to O'Hare Intl

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 271AverageC$ 527FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 686AverageC$ 958FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 704AverageC$ 870FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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.

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