Weekly flight availability from Chicago O'Hare Intl Airport to Winnipeg

The most flights from ORD to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

In terms of precipitation, rainfall in Winnipeg ranges from 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

If weather is an important factor for your trip to Winnipeg, 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 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

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: SkyWest Airlines (77%), United Airlines (77%), Air Canada (77%).

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.

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.

C$ 233+ Cheap Flights from Chicago O'Hare Intl Airport to Winnipeg

Cheap flight deals from O'Hare Intl to Winnipeg

Enter your travel dates to find the best prices.

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Cheapest flights from O'Hare Intl to Winnipeg
Explore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 October 2026.

Mon 14/1212:15 p.m. -

1 stop12h 29m

Wed 16/127:00 a.m. -

1 stop16h 00m

Deal found 19/10C$ 621

Thu 19/116:20 p.m. -

1 stop15h 55m

Sun 22/119:35 p.m. -

2 stops16h 09m

Deal found 16/10C$ 680

Thu 10/126:20 p.m. -

1 stop14h 55m

Sat 12/126:00 a.m. -

1 stop12h 40m

Deal found 19/10C$ 697

Mon 30/116:20 p.m. -

2 stops24h 54m

Mon 7/124:00 p.m. -

1 stop13h 01m

Deal found 15/10C$ 766

Wed 9/126:20 p.m. -

3 stops23h 54m

Fri 11/129:35 p.m. -

2 stops17h 55m

Deal found 20/10C$ 784

Fri 13/117:55 a.m. -

2 stops26h 20m

Fri 20/119:35 p.m. -

2 stops16h 09m

Deal found 15/10C$ 798

Find flight deals from O'Hare Intl to Winnipeg

Round-trip from	C$ 472
One-way from	C$ 233
Popular in	October
Cheapest in	September
Average price	C$ 1,498

5/1-25/1
2 total stops
57h 50m total
Chicago to Winnipeg

Search Deals

20/1-31/12
1 total stop
8h 40m total
Chicago to Winnipeg

Search Deals

High demand for flights, 7% potential price rise

Search Deals

Cheapest flight prices on average. 5% potential price decrease (C$ 77 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2026

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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

Sun 17/1

5:32 p.m.-2:40 p.m.

1 stop21h 08m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 276

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/11

7:35 p.m.-1:10 a.m.

2 stops29h 35m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 329

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 2/12

9:13 a.m.-5:25 p.m.

3 stops32h 12m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 360

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 30/11

7:49 a.m.-1:10 a.m.

2 stops17h 21m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 381

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 4/11

7:35 p.m.-1:10 a.m.

2 stops29h 35m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 395

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/11

2:50 p.m.-10:52 p.m.

1 stop8h 02m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 464

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 5/1

9:40 a.m.-2:40 p.m.

1 stop29h 00m

Winnipeg

Mon 25/1

9:35 p.m.-11:50 a.m.

2 stops14h 15m

C$ 481

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 26/10

6:10 a.m.-6:45 p.m.

1 stop12h 35m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 652

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 25/10

6:10 a.m.-10:10 a.m.

2 stops28h 00m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 667

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 19/11

6:20 p.m.-10:15 a.m.

1 stop15h 55m

Winnipeg

Sun 22/11

9:35 p.m.-1:44 p.m.

2 stops16h 09m

C$ 680

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/10

Showing 1-10 of 23 resultsSorted by cheapest first

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.

ORD-YWG

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 Chicago O'Hare Intl Airport to Winnipeg

Prices

Airlines

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.

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.
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: SkyWest Airlines (77%), United Airlines (77%), Air Canada (77%).
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.

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

Cheapflights helps you search for flights from O'Hare Intl to Winnipeg via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from O'Hare Intl to Winnipeg?

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.

Can Cheapflights notify me if prices for flights from O'Hare Intl to Winnipeg become cheaper?

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Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from C$ 233

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 20/1. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from O'Hare Intl to Winnipeg

Cheapest flights from O'Hare Intl to WinnipegExplore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 October 2026.

Explore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 October 2026.

Best flights from O'Hare Intl to WinnipegDiscover carefully curated flight deals from O'Hare Intl to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 20 October 2026.

Discover carefully curated flight deals from O'Hare Intl to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 20 October 2026.

Direct flights from O'Hare Intl to WinnipegExplore direct flight options from O'Hare Intl to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 20 October 2026.

Explore direct flight options from O'Hare Intl to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 20 October 2026.

Last-minute flights from O'Hare Intl to WinnipegDiscover last-minute flight deals from O'Hare Intl to Winnipeg. Data last updated 20 October 2026 and is based on user searches.

Discover last-minute flight deals from O'Hare Intl to Winnipeg. Data last updated 20 October 2026 and is based on user searches.

One-way flights from O'Hare Intl to WinnipegSearch for one-way flight options from O'Hare Intl to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 20 October 2026.

Search for one-way flight options from O'Hare Intl to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 20 October 2026.

Find flight deals from O'Hare Intl to Winnipeg

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

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.

Cheapflights Insights

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.

Weekly flight availability from Chicago O'Hare Intl Airport to Winnipeg

The most flights from ORD to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

Related info for your journey

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

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

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

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

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

Travelling to a place near Winnipeg?

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Search flights from O'Hare Intl to Winnipeg by cabin class

Find flights from O'Hare Intl to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.

O'Hare Intl and Winnipeg flights

Browse other O'Hare Intl and Winnipeg flight options. Last updated on 20 October 2026.

Other flights from O'Hare Intl

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Can Cheapflights notify me if prices for flights from O'Hare Intl to Winnipeg become cheaper?

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Cheapest flights from O'Hare Intl to Winnipeg
Explore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 October 2026.

Best flights from O'Hare Intl to Winnipeg
Discover carefully curated flight deals from O'Hare Intl to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 20 October 2026.

Direct flights from O'Hare Intl to Winnipeg
Explore direct flight options from O'Hare Intl to Winnipeg based on user searches, and compare prices and availability for your desired travel dates. Data last updated 20 October 2026.

Last-minute flights from O'Hare Intl to Winnipeg
Discover last-minute flight deals from O'Hare Intl to Winnipeg. Data last updated 20 October 2026 and is based on user searches.

One-way flights from O'Hare Intl to Winnipeg
Search for one-way flight options from O'Hare Intl to Winnipeg. Find affordable one-way fares based on user searches. Data last updated 20 October 2026.