Which airlines fly to Chicago O'Hare Intl Airport?

United Airlines, WestJet and Air Canada are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Winnipeg according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Winnipeg to Chicago O'Hare Intl?

WestJet is the most popular carrier operating from Winnipeg to Chicago O'Hare Intl

How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per week?

56 flights are operational weekly from Winnipeg to Chicago O'Hare Intl Airport as of August 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per day?

8 flights are operational daily from Winnipeg to Chicago O'Hare Intl Airport as of August 2026. The most popular departure time for this route is 7:00a.m., with 62% of flights per day taking off at noon.

When did momondo last update prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

Prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

The number of operators available for flights from Winnipeg Airport to Chicago O'Hare Intl Airport is 3 as of August 2026.

How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

C$ 284 Cheap Flights from Winnipeg to Chicago O'Hare Intl Airport in 2026

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Find the cheapest flights from Winnipeg to Chicago

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11:15 a.m. - 7:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 33m2 stops Montreal St Hubert Toronto Pearson Intl

9:50 a.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 05m1 stop Toronto Pearson Intl

C$ 506Multiple Airlines

Fri, 18 Sep - Fri, 25 Sep

6:55 p.m. - 11:05 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 10m1 stop Toronto Pearson Intl

6:10 p.m. - 9:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 05m1 stop Toronto Island

C$ 508Multiple Airlines

Sun, 25 Oct - Sun, 1 Nov

6:15 a.m. - 7:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

13h 33m1 stop Toronto Pearson Intl

2:20 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

10h 35m1 stop Toronto Pearson Intl

C$ 508Multiple Airlines

Fri, 18 Sep - Fri, 25 Sep

9:05 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

19h 35m1 stop Calgary

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

C$ 517WestJet

Fri, 28 Aug - Tue, 1 Sep

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

C$ 538WestJet

Wed, 26 Aug - Sat, 29 Aug

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 p.m. - 11:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

17h 40m1 stop Calgary

C$ 542WestJet

Thu, 10 Sep - Mon, 14 Sep

12:20 p.m. - 7:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 28m1 stop Toronto Pearson Intl

9:50 a.m. - 4:17 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Toronto Pearson Intl

C$ 690Air Canada

Tue, 13 Oct - Wed, 21 Oct

12:20 p.m. - 7:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 28m1 stop Toronto Pearson Intl

9:50 a.m. - 4:17 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Toronto Pearson Intl

C$ 691Air Canada

Tue, 13 Oct - Wed, 14 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 961United Airlines

Sun, 27 Sep - Tue, 29 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

6:00 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 57m1 stop Denver Intl

C$ 961United Airlines

Fri, 2 Oct - Sun, 4 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

6:40 a.m. - 9:47 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 07m1 stop Minneapolis St Paul

11:22 a.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 33m2 stops Detroit Metropolitan Wayne County Calgary

C$ 1,029WestJet

Sat, 8 Aug - Sat, 15 Aug

6:40 a.m. - 5:41 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

11h 01m1 stop Minneapolis St Paul

8:28 a.m. - 4:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 24m1 stop Minneapolis St Paul

C$ 1,034WestJet

Sat, 8 Aug - Sat, 15 Aug

10:45 a.m. - 2:09 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

27h 24m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

11:22 a.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 33m2 stops Detroit Metropolitan Wayne County Calgary

C$ 1,066WestJet

Sat, 8 Aug - Sat, 15 Aug

8:45 a.m. - 6:46 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

10h 01m1 stop Denver Intl

9:15 a.m. - 11:52 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,229United Airlines

Sat, 8 Aug - Sat, 15 Aug

7:00 a.m. - 9:34 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 34mdirect

1:30 p.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 27m1 stop Denver Intl

C$ 1,310United Airlines

Sat, 8 Aug - Mon, 10 Aug

7:00 a.m. - 9:34 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 34mdirect

8:00 p.m. - 10:38 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,310United Airlines

Sat, 8 Aug - Mon, 10 Aug

7:00 a.m. - 9:34 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 34mdirect

9:15 a.m. - 11:52 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,340Air Canada

Sat, 8 Aug - Sat, 15 Aug

2:55 p.m. - 12:44 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 49m2 stops Calgary Toronto Pearson Intl

2:53 a.m. - 11:10 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

32h 17m3 stops Guadalajara Miguel Hidal San José del Cabo Los Cabos Calgary

C$ 1,379Multiple Airlines

Fri, 7 Aug - Sat, 8 Aug

12:56 p.m. - 3:30 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 34mdirect

9:14 a.m. - 11:52 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,435Air Canada

Fri, 7 Aug - Sun, 9 Aug

6:15 a.m. - 8:55 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 40m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

8:32 p.m. - 11:19 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 47m1 stop Toronto Pearson Intl

C$ 1,456Multiple Airlines

Fri, 7 Aug - Sat, 8 Aug

Cheap direct flights

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7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 961United Airlines

Sun, 27 Sep - Tue, 29 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 961United Airlines

Wed, 7 Oct - Sun, 11 Oct

2:15 p.m. - 4:36 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 21mdirect

9:15 a.m. - 11:39 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 24mdirect

C$ 961United Airlines

Thu, 14 Jan - Tue, 19 Jan

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:15 a.m. - 11:52 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 961United Airlines

Thu, 10 Sep - Sat, 12 Sep

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,045Air Canada

Sat, 31 Oct - Fri, 6 Nov

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,046Air Canada

Fri, 18 Sep - Fri, 25 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

C$ 1,046Air Canada

Fri, 18 Sep - Fri, 25 Sep

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

C$ 1,048Multiple Airlines

Fri, 25 Sep - Sun, 27 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

C$ 1,048Multiple Airlines

Fri, 11 Sep - Mon, 14 Sep

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:15 a.m. - 11:52 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,058Multiple Airlines

Fri, 4 Sep - Fri, 11 Sep

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WestJet flights from Winnipeg to Chicago O'Hare Intl Airport

Our best WestJet deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets

WestJet

28 Aug

YWG9:05 p.m.Winnipeg

19h 35m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

1 Sep

ORD5:30 p.m.Chicago O'Hare Intl

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 517

WestJet

26 Aug

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

29 Aug

ORD5:30 p.m.Chicago O'Hare Intl

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 538

WestJet

10 Sep

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

14 Sep

ORD5:30 p.m.Chicago O'Hare Intl

17h 40m

1 stop

YWG11:10 a.m.Winnipeg

C$ 542

United Airlines flights from Winnipeg to Chicago O'Hare Intl Airport

Our best United Airlines deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets

United Airlines

19 Aug

YWG8:45 a.m.Winnipeg

14h 01m

1 stop

ORD10:46 p.m.Chicago O'Hare Intl

21 Aug

ORD9:15 a.m.Chicago O'Hare Intl

2h 37m

YWG11:52 a.m.Winnipeg

C$ 1,136

United Airlines

15 Aug

YWG5:15 a.m.Winnipeg

16h 45m

2 stops

ORD10:00 p.m.Chicago O'Hare Intl

31 Aug

ORD9:40 p.m.Chicago O'Hare Intl

13h 35m

2 stops

YWG11:15 a.m.Winnipeg

C$ 1,176

United Airlines

8 Aug

YWG8:45 a.m.Winnipeg

10h 01m

1 stop

ORD6:46 p.m.Chicago O'Hare Intl

15 Aug

ORD9:15 a.m.Chicago O'Hare Intl

2h 37m

YWG11:52 a.m.Winnipeg

C$ 1,229

momondo 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

Fri 18/9

11:15 a.m.-7:48 p.m.

2 stops8h 33m

Chicago O'Hare Intl

Fri 25/9

9:50 a.m.-12:55 a.m.

1 stop15h 05m

C$ 506

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 25/10

6:55 p.m.-11:05 a.m.

1 stop16h 10m

Chicago O'Hare Intl

Sun 1/11

6:10 p.m.-9:15 a.m.

1 stop15h 05m

C$ 508

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 18/9

6:15 a.m.-7:48 p.m.

1 stop13h 33m

Chicago O'Hare Intl

Fri 25/9

2:20 p.m.-12:55 a.m.

1 stop10h 35m

C$ 508

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 28/8

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

1 stop19h 35m

Chicago O'Hare Intl

Tue 1/9

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

1 stop7h 25m

C$ 517

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 26/8

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Sat 29/8

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

1 stop7h 25m

C$ 538

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/9

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Mon 14/9

5:30 p.m.-11:10 a.m.

1 stop17h 40m

C$ 542

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 13/10

12:20 p.m.-7:48 p.m.

1 stop7h 28m

Chicago O'Hare Intl

Wed 21/10

9:50 a.m.-4:17 p.m.

1 stop6h 27m

C$ 690

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 13/10

12:20 p.m.-7:48 p.m.

1 stop7h 28m

Chicago O'Hare Intl

Wed 14/10

9:50 a.m.-4:17 p.m.

1 stop6h 27m

C$ 691

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 27/9

7:00 a.m.-9:35 a.m.

Nonstop2h 35m

Chicago O'Hare Intl

Tue 29/9

10:00 a.m.-12:37 p.m.

Nonstop2h 37m

C$ 961

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 2/10

7:00 a.m.-9:35 a.m.

Nonstop2h 35m

Chicago O'Hare Intl

Sun 4/10

6:00 a.m.-8:57 p.m.

1 stop14h 57m

C$ 961

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Winnipeg to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Winnipeg and Chicago O'Hare Intl Airport?

Prices are currently low for flights on this route.

Typical prices usually range from C$ 518 to C$ 806.
The lowest price recently found on this route was C$ 506.

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

In general, September is the cheapest month to fly from Winnipeg to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 496. The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around C$ 678.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as C$ 815. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago O'Hare Intl Airport for around C$ 1,169.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the morning is the cheapest time of day to fly from Winnipeg to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 870. Flying to Chicago O'Hare Intl Airport in the morning is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 983 on average. Flights to Chicago O'Hare Intl Airport from Winnipeg at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago O'Hare Intl flight prices

What cabin class options are available on Winnipeg to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Winnipeg to Chicago O'Hare Intl Airport flights?

You could potentially save up to 28% on your flight if you consider stops on a Winnipeg to Chicago O'Hare Intl Airport flight.

How have Winnipeg to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Winnipeg to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Winnipeg to Chicago O'Hare Intl Airport (YWG to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago O'Hare Intl Airport

Best price found	C$ 552
Fastest flight time	2h 21m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is C$ 552. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 702.

The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 21m

Direct flights go from Winnipeg to Chicago O'Hare Intl Airport every day.

Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago O'Hare Intl Airport

How far is Winnipeg to Chicago O'Hare Intl by plane?
Winnipeg and Chicago O'Hare Intl are 1130.2 km apart from one another. Flights usually cover this in 2h 21m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?
Prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?
The number of operators available for flights from Winnipeg Airport to Chicago O'Hare Intl Airport is 3 as of August 2026.
How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Winnipeg to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked plane model on the route from Winnipeg to Chicago O'Hare Intl Airport is Embraer 175 (Enhanced Winglets), representing 81.36% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 6.78%, Boeing 737 MAX 8 at 5.08%, and Boeing 737 MAX 9 at 1.69%.
What is the most popular airline from Winnipeg to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from Winnipeg to Chicago O'Hare Intl Airport is United Airlines, representing 46% of all bookings. The subsequent popular airlines are WestJet at 32% and Air Canada at 22%.

Best airlines flying from Winnipeg to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Winnipeg to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom C$ 275	Free Cancellation	Rating 7.2 3,426 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 494	Free Cancellation	Rating 7.4 10,064 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 715	Free Cancellation	Rating 7.1 11,429 reviews	Search Air Canada flights

United Airlines Flights From Winnipeg to Chicago O'Hare Intl Airport
United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 14 times per week, with 10,072 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Winnipeg to Chicago O'Hare Intl Airport in the last 72 hours was C$ 494 (round-trip), much lower than the average airfare cost of C$ 963 for United Airlines flights on this route.
Air Canada Flights From Winnipeg to Chicago O'Hare Intl Airport
Air Canada is also a popular choice for this route. Air Canada flight deals for Winnipeg to Chicago O'Hare Intl Airport start from as low as C$ 715 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 918. Air Canada operates 14 flights to Chicago O'Hare Intl Airport from Winnipeg in an average week. Users have rated it 7.1/10 across 11,429 reviews.

Schaumburg

Crystal Lake

Glenview

Waukegan

Rosemont

Des Plaines

Merrillville

Kenosha

Northbrook

Skokie

Tinley Park

Evanston

Downers Grove

Great Lakes

Hammond

Naperville

Harvey

Munster

Hoffman Estates

Elmhurst

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Winnipeg to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?

All flight searches from Winnipeg to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Winnipeg to Chicago?

Once you have performed a search for Winnipeg to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Winnipeg to Chicago from C$ 284

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 10/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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WestJet flights from Winnipeg to Chicago O'Hare Intl Airport

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