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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 210

ORD — YWG
9 Oct — 16 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from O'Hare Intl to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from O'Hare Intl to Winnipeg

Fri 2/105:30 p.m. -
1 stop7h 25m
Sun 4/107:00 a.m. -
1 stop9h 40m
Deal found 8/9C$ 454
Thu 15/105:30 p.m. -
1 stop7h 25m
Mon 19/107:00 a.m. -
1 stop9h 40m
Deal found 6/9C$ 455
Sun 4/105:30 p.m. -
1 stop7h 25m
Sun 11/107:00 a.m. -
1 stop9h 40m
Deal found 6/9C$ 459
Mon 5/105:30 p.m. -
1 stop7h 25m
Mon 12/107:00 a.m. -
1 stop9h 40m
Deal found 8/9C$ 468
Fri 18/95:30 p.m. -
1 stop7h 25m
Mon 21/92:55 p.m. -
1 stop25h 45m
Deal found 4/9C$ 517
Fri 2/105:30 p.m. -
1 stop7h 25m
Fri 9/106:15 a.m. -
2 stops33h 15m
Deal found 4/9C$ 523
Thu 15/105:30 p.m. -
1 stop7h 25m
Tue 20/109:20 a.m. -
1 stop6h 54m
Deal found 4/9C$ 525
Fri 23/105:30 p.m. -
1 stop7h 25m
Fri 30/107:00 a.m. -
1 stop7h 20m
Deal found 7/9C$ 530
Mon 5/105:30 p.m. -
1 stop7h 25m
Mon 12/105:00 p.m. -
2 stops37h 34m
Deal found 5/9C$ 532
Mon 19/108:04 a.m. -
2 stops16h 51m
Mon 26/104:00 p.m. -
1 stop13h 16m
Deal found 4/9C$ 535
Fri 2/106:30 a.m. -
2 stops13h 45m
Sun 4/107:00 a.m. -
1 stop9h 40m
Deal found 8/9C$ 542

Find flight deals from O'Hare Intl to Winnipeg

Round-trip from

C$ 454

One-way from

C$ 210

Popular in

September

Cheapest in

October

Average price

C$ 1,563

Good one-way deal

C$ 540 or less
WestJet
  • WestJet
  • 2/10-4/10
  • 2 total stops
  • 17h 05m total
  • Chicago to Winnipeg
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WestJet
  • WestJet
  • 27/9-31/12
  • 1 total stop
  • 7h 25m total
  • Chicago to Winnipeg
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 105 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease (C$ 82 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 one-way flight from Chicago O'Hare Intl to Winnipeg.
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Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 14/10

2:15 p.m.-12:55 a.m.

1 stop10h 40m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 219
Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 18/9

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 223

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 23/9

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

1 stop12h 00m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 263

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 12/10

5:30 p.m.-3:25 p.m.

1 stop21h 55m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 273

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 30/9

7:25 a.m.-12:55 a.m.

3 stops41h 30m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 287

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 30/9

11:42 a.m.-7:54 p.m.

1 stop8h 12m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 330

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 2/3

2:54 p.m.-9:55 p.m.

3 stops31h 01m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 404

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

5:30 p.m.-9:20 a.m.

2 stops15h 50m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 405

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 18/9

6:30 a.m.-2:40 p.m.

3 stops32h 10m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 408

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 25/10

6:20 p.m.-4:10 p.m.

1 stop21h 50m

Winnipeg

Fri 30/10

8:05 p.m.-11:40 a.m.

1 stop15h 35m

C$ 694

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 19 resultsSorted by cheapest first
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Best time to book a flight from O'Hare Intl to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from O'Hare Intl with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Winnipeg

What is the cheapest time of day to fly from ORD to YWG?

When flying from Chicago O'Hare Intl Airport to Winnipeg, 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 Chicago O'Hare Intl Airport to Winnipeg?

Airfare is typical for this route at the moment.

Chicago O'Hare Intl Airport to Winnipeg flights typically cost between C$ 352 and C$ 1,585 in October.
The cheapest round-trip price found within the last 5 days was C$ 454 on WestJet (2 Oct-4 Oct).

Related info for your journey

  • What airport do you fly into for flights to Winnipeg from Chicago O'Hare Intl?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago O'Hare Intl. On average, Winnipeg has 6 inbound flights from Chicago O'Hare Intl per day from 0 airlines. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

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

    Departing from Chicago O'Hare Intl Airport to Winnipeg will take you 7h 16m. Chicago O'Hare Intl Airport and Winnipeg are separated by a distance of 1136 km.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Winnipeg?

    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 Chicago O'Hare Intl Airport to Winnipeg on time: Copa Airlines (65%), SkyWest Airlines (64%), Air Canada (64%).

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

    Looking at all options, your cheapest flight can be booked for C$ 465. While the most popular route (Chicago O'Hare Intl - Winnipeg) can be booked for C$ 530 on average, our data indicates C$ 580 when flying from Chicago O'Hare Intl Airport to Winnipeg.

  • Can I find deals for flights from O'Hare Intl to Winnipeg that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Winnipeg.

  • Can I find deals for business class flights from O'Hare Intl to Winnipeg?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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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 Winnipeg from O'Hare Intl.

Can Cheapflights find flights from O'Hare Intl to Winnipeg with no change fees?

Certainly. Search results for flights to Winnipeg from O'Hare Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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