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 35% 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.

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

7 flights are operational daily from Winnipeg to Chicago O'Hare Intl Airport as of September 2026. The most popular departure time for this route is 2:00p.m., with 53% of flights per day taking off in the afternoon.

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

50 flights are operational weekly from Winnipeg to Chicago O'Hare Intl Airport as of September 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

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

WestJet and Porter Airlines are the most popular carriers operating from Winnipeg to Chicago O'Hare Intl

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 September 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$ 240 Cheap Flights from Winnipeg to Chicago O'Hare Intl Airport in 2026/27

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Find the cheapest flights from Winnipeg to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

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$ 410WestJet

Mon, 19 Oct - Thu, 22 Oct

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$ 471WestJet

Sun, 18 Oct - Mon, 19 Oct

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

9h 40m1 stop Calgary

6:20 p.m. - 6:10 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 50m2 stops Toronto Island Ottawa

C$ 480Multiple Airlines

Fri, 23 Oct - Tue, 27 Oct

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

9h 40m1 stop Calgary

6:20 p.m. - 6:10 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 50m2 stops Toronto Island Ottawa

C$ 484Multiple Airlines

Thu, 22 Oct - Tue, 27 Oct

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

9h 40m1 stop Calgary

6:20 p.m. - 9:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 487Multiple Airlines

Fri, 23 Oct - Tue, 27 Oct

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

9h 40m1 stop Calgary

5:30 p.m. - 9:35 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 05m2 stops Calgary Saskatoon

C$ 491WestJet

Mon, 19 Oct - Thu, 22 Oct

5:00 a.m. - 1:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 668Air Canada

Tue, 13 Oct - Thu, 15 Oct

5:00 a.m. - 1:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 668Air Canada

Sun, 18 Oct - Tue, 20 Oct

11:05 a.m. - 9:15 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

22h 10m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

6:20 p.m. - 11:49 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

17h 29m2 stops Boston Logan Intl Toronto Pearson Intl

C$ 923United Airlines

Mon, 7 Dec - Tue, 8 Dec

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

2h 35mdirect

10:55 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

10h 02m1 stop Denver Intl

C$ 950United Airlines

Sun, 1 Nov - Sun, 8 Nov

Cheap last-minute flights

Enter your travel dates to find the best prices.

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

9h 40m1 stop Calgary

8:03 a.m. - 3:19 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 16m1 stop Toronto Pearson Intl

C$ 708Multiple Airlines

Tue, 22 Sep - Wed, 30 Sep

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

9h 40m1 stop Calgary

12:29 p.m. - 10:10 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

9h 41m2 stops Minneapolis St Paul Calgary

C$ 741WestJet

Tue, 22 Sep - Wed, 30 Sep

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

9h 40m2 stops Edmonton Calgary

2:05 p.m. - 8:00 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

29h 55m2 stops Salt Lake City Vancouver Intl

C$ 941WestJet

Tue, 22 Sep - Wed, 30 Sep

7:20 a.m. - 5:05 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 45m1 stop Calgary

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 1,058Air Canada

Wed, 23 Sep - Wed, 30 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$ 1,058WestJet

Wed, 23 Sep - Mon, 28 Sep

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

2h 35mdirect

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 1,121Air Canada

Wed, 23 Sep - Wed, 30 Sep

9:20 a.m. - 4:18 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 58m1 stop Toronto Pearson Intl

8:30 p.m. - 10:43 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 13m2 stops Toronto Pearson Intl Ottawa

C$ 1,277Porter Airlines

Tue, 22 Sep - Wed, 30 Sep

9:20 a.m. - 4:18 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 58m1 stop Toronto Pearson Intl

3:42 p.m. - 3:20 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 38m1 stop Toronto Pearson Intl

C$ 1,280Porter Airlines

Tue, 22 Sep - Wed, 30 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$ 1,574United Airlines

Fri, 18 Sep - Sun, 20 Sep

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

2h 35mdirect

5:00 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 57m1 stop Denver Intl

C$ 1,577United Airlines

Fri, 18 Sep - Sun, 20 Sep

Cheap direct flights

Enter your travel dates to find the best prices.

7:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mdirect

3:50 p.m. - 6:41 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mdirect

C$ 950United Airlines

Thu, 25 Feb - Sun, 28 Feb

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$ 950United Airlines

Wed, 18 Nov - Sun, 22 Nov

2:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mdirect

10:00 a.m. - 12:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mdirect

C$ 951United Airlines

Thu, 31 Dec - Sun, 3 Jan

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$ 953United Airlines

Sat, 17 Oct - Sun, 18 Oct

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$ 1,100Multiple Airlines

Thu, 29 Oct - Sun, 1 Nov

2:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mdirect

10:00 a.m. - 12:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mdirect

C$ 1,131Air Canada

Wed, 30 Dec - Mon, 4 Jan

2:15 p.m. - 5:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

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

2h 48mdirect

C$ 1,132Air Canada

Fri, 11 Dec - Sun, 13 Dec

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

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 1,134Air Canada

Thu, 22 Oct - Tue, 27 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$ 1,134Multiple Airlines

Sun, 18 Oct - Tue, 20 Oct

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$ 1,134Multiple Airlines

Fri, 6 Nov - Mon, 9 Nov

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Air Canada flights from Winnipeg to Chicago O'Hare Intl Airport

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

Air Canada

13 Oct

YWG5:00 a.m.Winnipeg

8h 23m

1 stop

ORD1:23 p.m.Chicago O'Hare Intl

20 Oct

ORD3:45 p.m.Chicago O'Hare Intl

8h 02m

1 stop

YWG11:47 p.m.Winnipeg

C$ 668

Air Canada

28 Sep

YWG5:25 p.m.Winnipeg

19h 58m

1 stop

ORD1:23 p.m.Chicago O'Hare Intl

30 Sep

ORD10:43 a.m.Chicago O'Hare Intl

7h 29m

1 stop

YWG6:12 p.m.Winnipeg

C$ 916

Air Canada

28 Sep

YWG5:25 p.m.Winnipeg

19h 58m

1 stop

ORD1:23 p.m.Chicago O'Hare Intl

30 Sep

ORD10:43 a.m.Chicago O'Hare Intl

7h 29m

1 stop

YWG6:12 p.m.Winnipeg

C$ 978

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

19 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

22 Oct

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 410

WestJet

18 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

19 Oct

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

17h 40m

1 stop

YWG11:10 a.m.Winnipeg

C$ 471

WestJet

19 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

22 Oct

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

16h 05m

2 stops

YWG9:35 a.m.Winnipeg

C$ 491

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

Mon 19/10

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

1 stop9h 40m

Chicago O'Hare Intl

Thu 22/10

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

1 stop7h 25m

C$ 410

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 18/10

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 19/10

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

1 stop17h 40m

C$ 471

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 23/10

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 27/10

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

2 stops23h 50m

C$ 480

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 22/10

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 27/10

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

2 stops23h 50m

C$ 484

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 23/10

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 27/10

6:20 p.m.-9:15 a.m.

1 stop14h 55m

C$ 487

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 19/10

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

1 stop9h 40m

Chicago O'Hare Intl

Thu 22/10

5:30 p.m.-9:35 a.m.

2 stops16h 05m

C$ 491

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 13/10

5:00 a.m.-1:23 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Thu 15/10

9:55 a.m.-6:12 p.m.

1 stop8h 17m

C$ 668

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 18/10

5:00 a.m.-1:23 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Tue 20/10

9:55 a.m.-6:12 p.m.

1 stop8h 17m

C$ 668

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 7/12

11:05 a.m.-9:15 a.m.

2 stops22h 10m

Chicago O'Hare Intl

Tue 8/12

6:20 p.m.-11:49 a.m.

2 stops17h 29m

C$ 923

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 1/11

2:15 p.m.-4:50 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Sun 8/11

10:55 a.m.-8:57 p.m.

1 stop10h 02m

C$ 950

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$ 549 to C$ 876.
The lowest price recently found on this route was C$ 410.

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

In general, February 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$ 692. The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around C$ 718.

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$ 833. 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$ 1,161.

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$ 890. 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$ 990 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 38% 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$ 240
Fastest flight time	2h 31m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is C$ 240. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 410.

The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 31m

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 31m, 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 September 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 86.67% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 5.93%, Boeing 737 MAX 8 at 2.96%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 1.48%.
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 35% of all bookings. The subsequent popular airlines are WestJet at 35% and Air Canada at 30%.

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$ 273	Free Cancellation	Rating 7.2 3,446 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 692	Free Cancellation	Rating 7.4 10,214 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 710	Free Cancellation	Rating 7.1 11,640 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 11 times per week, with 10,213 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$ 692 (round-trip), much lower than the average airfare cost of C$ 965 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$ 710 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 877. 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 11,640 reviews.

Crystal Lake

Schaumburg

Waukegan

Glenview

Rosemont

Des Plaines

Merrillville

Kenosha

Tinley Park

Northbrook

Skokie

Evanston

Benton Harbor

Hammond

Downers Grove

Naperville

Munster

Harvey

Monroe

Hoffman Estates

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$ 240

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 18/10. 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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Air Canada flights from Winnipeg to Chicago O'Hare Intl Airport

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