How long does a flight from Chicago to Winnipeg take?

A direct flight to Winnipeg will take on average 2h 29m to travel the 1,829 km flying distance from Chicago. Visit our flight page for the latest deals!>/a>

How many flights are there between Chicago O'Hare Intl Airport and Winnipeg per day?

Each day, there are 2 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Winnipeg, with an average flight time of 2h 31m. The most common departure time is 7:00 p.m. and most flights take off in the afternoon. Each week, there are 14 flights and there are the same amount of flights each day (2). Visit our flight page for the latest deals!>/a>

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

In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was C$ 111 for a one-way ticket and C$ 258 for a round-trip. Visit our flight page for the latest deals!>/a>

Which airports will I be using when flying from Chicago to Winnipeg?

Chicago airport is called Chicago O'Hare Intl and the only airport in Winnipeg is Winnipeg. Visit our flight page for the latest deals!>/a>

What’s the earliest departure time from Chicago to Winnipeg?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 1:02 pm and will be landing in Winnipeg at 3:31 pm.

What’s the latest departure time from Chicago to Winnipeg?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Winnipeg jets off at 7:58 pm and lands at 10:33 pm.

Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

Which aircraft models fly most regularly from Chicago to Winnipeg?

The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.

Which airline alliances offer flights from Chicago to Winnipeg?

Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.

On which days can I fly direct from Chicago to Winnipeg?

There are direct flights from Chicago to Winnipeg on a daily basis.

How does KAYAK find such low prices on flights from Chicago to Winnipeg?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Winnipeg. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago is likely to change within 7 days, so travellers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Chicago to Winnipeg?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Winnipeg?

There is only one cabin class option available for the route, which is Economy . Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Which airlines provide the cheapest flights from Chicago to Winnipeg?

In the past 3 days, the cheapest round-trip tickets from Chicago to Winnipeg were found on WestJet (C$ 392) and Delta (C$ 632).

C$ 152 CHEAP FLIGHTS from Chicago to Winnipeg (ORD - YWG)

ORD - YWG

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

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Flights Deals

Cheap Flights from Chicago to Winnipeg (ORD-YWG)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Chicago to Winnipeg

Tue, 8 Jul - Fri, 11 Jul

10:43 a.m. - 12:31 a.m.ORD-YWG

13h 48m2 stops

9:00 a.m. - 9:30 p.m.YWG-ORD

12h 30m1 stop

C$ 353

Find Deal

Tue, 8 Jul - Fri, 18 Jul

10:43 a.m. - 12:31 a.m.ORD-YWG

13h 48m2 stops

9:00 a.m. - 9:30 p.m.YWG-ORD

12h 30m1 stop

C$ 357

Find Deal

Tue, 8 Jul - Fri, 11 Jul

10:43 a.m. - 12:31 a.m.ORD-YWG

13h 48m2 stops

9:00 a.m. - 9:30 p.m.YWG-ORD

12h 30m1 stop

C$ 360

Find Deal

Wed, 24 Sep - Fri, 26 Sep

6:00 a.m. - 4:22 p.m.ORD-YWG

10h 22m1 stop

9:00 a.m. - 4:18 p.m.YWG-ORD

7h 18m1 stop

C$ 369

Find Deal

Fri, 17 Oct - Mon, 20 Oct

5:30 p.m. - 9:30 p.m.ORD-YWG

28h 00m1 stop

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

8h 13m1 stop

C$ 392WestJet

Find Deal

Fri, 5 Sep - Wed, 10 Sep

5:30 p.m. - 11:41 a.m.ORD-YWG

18h 11m1 stop

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

8h 13m1 stop

C$ 406WestJet

Find Deal

Wed, 24 Sep - Tue, 30 Sep

7:00 a.m. - 8:15 p.m.ORD-YWG

13h 15m2 stops

6:40 a.m. - 11:53 p.m.YWG-ORD

17h 13m2 stops

C$ 632Delta

Find Deal

Mon, 22 Sep - Wed, 1 Oct

7:00 a.m. - 11:32 p.m.ORD-YWG

16h 32m2 stops

6:40 a.m. - 9:46 p.m.YWG-ORD

15h 06m2 stops

C$ 637Delta

Find Deal

Tue, 28 Oct - Fri, 7 Nov

2:00 p.m. - 8:58 p.m.ORD-YWG

6h 58m1 stop

5:15 a.m. - 10:58 a.m.YWG-ORD

5h 43m1 stop

C$ 701Air Canada

Find Deal

Sat, 26 Jul - Sat, 2 Aug

7:58 p.m. - 10:33 p.m.ORD-YWG

2h 35mdirect

6:35 p.m. - 9:09 a.m.YWG-ORD

14h 34m1 stop

C$ 715Air Canada

Find Deal

Expert advice

Expert advice for your flight from Chicago to Winnipeg

KAYAK teamed up with top travel experts to share the best tips for your journey.

Airlines

United Airlines

United's Economy Plus offers up to 15 cm more legroom than standard economy seats.

United's Priority Boarding places you in Zone 2, avoiding overhead bin space issues.

Read more about United Airlinesby Stefanie Waldek

Air Canada

Air Canada's Preferred Economy seats offer up to 10 extra cm of legroom.

Air Canada offers priority check-in for higher fare classes and elite status travelers.

Read more about Air Canadaby Stefanie Waldek

Airports

ORD

For a quick security check, avoid peak times at ORD as lines can exceed 30 minutes. Off-peak hours are much faster.

KAYAK's insights & trends for Chicago to Winnipeg flights

Get data-powered insights and trends into flights from Chicago to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

Prices

Airlines

If your flying dates are flexible, you should consider flying to Winnipeg on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago to Winnipeg. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost C$ 314 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is C$ 916 and C$ 887 respectively.

Find deals

Low season	January
High season	July
Cheapest flight	C$ 152

Best time to beat the crowds but there is an average 13% increase in price.

Most popular time to fly (27% more expensive on average)

Flight from Chicago to Winnipeg

When to book flights from Chicago to Winnipeg

Are your dates flexible? Find out the best times to travel from Chicago to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated round-trip price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

What is the cheapest flight from Chicago O'Hare Intl Airport to Winnipeg?
In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was C$ 111 for a one-way ticket and C$ 258 for a round-trip.
Which airports will I be using when flying from Chicago to Winnipeg?
Chicago airport is called Chicago O'Hare Intl and the only airport in Winnipeg is Winnipeg.
Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?
Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.
Which aircraft models fly most regularly from Chicago to Winnipeg?
The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.
Which airline alliances offer flights from Chicago to Winnipeg?
Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.
On which days can I fly direct from Chicago to Winnipeg?
There are direct flights from Chicago to Winnipeg on a daily basis.
How does KAYAK find such low prices on flights from Chicago to Winnipeg?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Winnipeg.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.
What is the Hacker Fare option on flights from Chicago to Winnipeg?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Looking for a cheap flight? 25% of our users found flights on this route for C$ 344 or less one-way.

Direct departures

Chicago O'Hare Intl to Winnipeg

Monday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Tuesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Wednesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Thursday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Friday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Saturday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Sunday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

See more nonstop flights

Direct returns

Winnipeg to Chicago O'Hare Intl

Monday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Tuesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Wednesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Thursday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Friday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Saturday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Sunday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

See more nonstop flights

Top airline flying from Chicago to Winnipeg

Need help choosing which airline to fly with from Chicago to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.

7.1

Air CanadaOverall score based on 9531 reviews

7.3Boarding

7.0Comfort

6.3Food

6.8Entertainment

7.8Crew

Airline reviews

Flight was delayed but the real issue is how long we sat after boarding. Space very limited for an overnight flight and seatbacks didn’t recline so it was almost impossible to sleep.

6.0 GoodAnonymous, Jun 2025CMH - YYZ

Everything you need to know for your flight from Chicago to Winnipeg

Airports

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Information on your arrival and departure airports

Chicago (ORD)

Winnipeg (YWG)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

ORD - YWG

C$ 152 Find Cheap Flights from Chicago to Winnipeg

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

Cheap Flights from Chicago to Winnipeg (ORD-YWG)

Recent round-trip flight deals from Chicago to Winnipeg

Recent one-way flight deals from Chicago to Winnipeg

Recent last minute flight deals from Chicago to Winnipeg

Recent direct flight deals from Chicago to Winnipeg

Expert advice for your flight from Chicago to Winnipeg

KAYAK's insights & trends for Chicago to Winnipeg flights

Get data-powered insights and trends into flights from Chicago to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Winnipeg?

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost C$ 314 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is C$ 916 and C$ 887 respectively.

Which airlines provide the cheapest flights from Chicago to Winnipeg?

In the past 3 days, the cheapest round-trip tickets from Chicago to Winnipeg were found on WestJet (C$ 392) and Delta (C$ 632).

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Winnipeg?

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How many flights are there between Chicago O'Hare Intl Airport and Winnipeg per day?

How long does a flight from Chicago to Winnipeg take?

A direct flight to Winnipeg will take on average 2h 29m to travel the 1,829 km flying distance from Chicago.

What’s the earliest departure time from Chicago to Winnipeg?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 1:02 pm and will be landing in Winnipeg at 3:31 pm.

What’s the latest departure time from Chicago to Winnipeg?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Winnipeg jets off at 7:58 pm and lands at 10:33 pm.

Good to know

When to book flights from Chicago to Winnipeg

FAQs for booking Chicago to Winnipeg flights

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

In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was C$ 111 for a one-way ticket and C$ 258 for a round-trip.

Which airports will I be using when flying from Chicago to Winnipeg?

Chicago airport is called Chicago O'Hare Intl and the only airport in Winnipeg is Winnipeg.

Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

Which aircraft models fly most regularly from Chicago to Winnipeg?

The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.

Which airline alliances offer flights from Chicago to Winnipeg?

Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.

On which days can I fly direct from Chicago to Winnipeg?

There are direct flights from Chicago to Winnipeg on a daily basis.

How does KAYAK find such low prices on flights from Chicago to Winnipeg?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Winnipeg.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

What is the Hacker Fare option on flights from Chicago to Winnipeg?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Winnipeg

Prefer to fly direct from Chicago to Winnipeg?

Top airline flying from Chicago to Winnipeg

Everything you need to know for your flight from Chicago to Winnipeg

Information on your arrival and departure airports

Cabin class types available on flights to Winnipeg

Complete your trip to Winnipeg with a hotel stay or car rental

Find direct flights to and from Chicago and Winnipeg

Flights to other popular destinations

Flights from domestic origins to Winnipeg

Choose which airport to fly into in Chicago

Find deals for your return flight