How many flights depart from Manitoba to Chicago on average per week?

22 flights are operational weekly from Manitoba to Chicago as of September 2026. The most popular departure day for this route is Mon, with 36% of flights per week taking off on this day.

What is the cheapest airline that flies from Manitoba to Chicago?

Porter Airlines is the most popular carrier operating from Manitoba to Chicago

How many flights depart from Manitoba to Chicago on average per day?

3 flights are operational daily from Manitoba to Chicago as of September 2026. The most popular departure time for this route is 7:00a.m., with 50% of flights per day taking off at noon.

Which airlines fly to Chicago?

United Airlines, WestJet and Air Canada are the top three most popular airlines that fly to Chicago from Manitoba 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. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Manitoba to Chicago?

Prices for flights from Manitoba to Chicago refresh daily.

How many operators does momondo search for flights from Manitoba to Chicago?

There are 3 operators available for flights from Manitoba to Chicago as of September 2026.

How old do you have to be to fly from Manitoba to Chicago?

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 Manitoba to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 285 Cheap Flights from Manitoba to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Manitoba to Chicago

Round-trip

One-way

Last minute

Direct

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$ 452WestJet

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

16h 05m2 stops Calgary Saskatoon

C$ 469WestJet

Mon, 19 Oct - Fri, 23 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$ 487WestJet

Mon, 19 Oct - Fri, 23 Oct

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

9h 40m1 stop Calgary

6:20 p.m. - 2:20 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

20h 00m2 stops Toronto Island Calgary

C$ 493Multiple Airlines

Thu, 22 Oct - Sun, 25 Oct

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

9h 40m1 stop Calgary

12:20 p.m. - 9:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

20h 55m1 stop Toronto Island

C$ 499Multiple Airlines

Thu, 22 Oct - Sun, 25 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$ 499Multiple Airlines

Thu, 22 Oct - Mon, 26 Oct

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

8h 23m1 stop Toronto Pearson Intl

4:30 p.m. - 11:59 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 29m1 stop Toronto Pearson Intl

C$ 727Air Canada

Wed, 21 Oct - Wed, 28 Oct

5:15 a.m. - 1:13 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 58m1 stop Toronto Pearson Intl

4:30 p.m. - 11:44 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 14m1 stop Toronto Pearson Intl

C$ 734Air Canada

Thu, 12 Nov - Tue, 17 Nov

3:20 p.m. - 7:59 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 39m2 stops Toronto Pearson Intl Boston Logan Intl

8:01 p.m. - 11:49 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 48m2 stops Boston Logan Intl Toronto Pearson Intl

C$ 879United Airlines

Mon, 19 Oct - Mon, 26 Oct

3:20 p.m. - 9:00 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

17h 40m2 stops Toronto Pearson Intl Boston Logan Intl

9:24 p.m. - 11:12 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 48m2 stops Boston Logan Intl Toronto Pearson Intl

C$ 933United Airlines

Sat, 10 Oct - Tue, 13 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

4:55 p.m. - 9:00 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 05m2 stops Calgary Toronto Pearson Intl

5:30 p.m. - 2:05 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

20h 35m1 stop Calgary

C$ 831Multiple Airlines

Tue, 29 Sep - Tue, 6 Oct

4:55 p.m. - 9:00 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 05m2 stops Calgary Toronto Pearson Intl

11:05 a.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 50m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Island

C$ 851Multiple Airlines

Tue, 29 Sep - Tue, 6 Oct

5:44 p.m. - 9:33 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

3h 49m1 stop Minneapolis St Paul

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

7h 25m1 stop Calgary

C$ 912WestJet

Tue, 29 Sep - Tue, 6 Oct

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

2h 35mdirect

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

7h 25m1 stop Calgary

C$ 930Multiple Airlines

Tue, 29 Sep - Tue, 6 Oct

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

2h 35mdirect

4:30 p.m. - 11:59 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 29m1 stop Toronto Pearson Intl

C$ 1,105Air Canada

Sat, 26 Sep - Wed, 28 Oct

10:50 a.m. - 8:12 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 22m1 stop Montreal Pierre Elliott Trudeau Intl

4:30 p.m. - 11:59 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 29m1 stop Toronto Pearson Intl

C$ 1,110Air Canada

Sat, 26 Sep - Wed, 28 Oct

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$ 1,303United Airlines

Mon, 28 Sep - Wed, 30 Sep

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

2h 35mdirect

2:30 p.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Denver Intl

C$ 1,303United Airlines

Mon, 28 Sep - Wed, 30 Sep

6:00 a.m. - 9:37 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 37m2 stops Calgary New York John F Kennedy Intl

5:27 a.m. - 5:25 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

11h 58m2 stops Atlanta Hartsfield-Jackson Calgary

C$ 1,341WestJet

Sat, 26 Sep - Wed, 28 Oct

6:40 a.m. - 5:59 p.m.YWG Winnipeg-MDW Chicago Midway

11h 19m1 stop Minneapolis St Paul

10:59 a.m. - 1:10 a.m.MDW Chicago Midway-YWG Winnipeg

14h 11m2 stops Atlanta Hartsfield-Jackson Calgary

C$ 1,341WestJet

Sat, 26 Sep - Wed, 28 Oct

Cheap direct flights

Enter your travel dates to find the best prices.

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$ 952United Airlines

Wed, 18 Nov - Sun, 22 Nov

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$ 955United Airlines

Tue, 16 Mar - Tue, 16 Mar

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$ 955United Airlines

Wed, 18 Nov - Sun, 22 Nov

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$ 957United Airlines

Wed, 18 Nov - Sun, 22 Nov

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$ 1,076Air Canada

Fri, 11 Dec - Sun, 13 Dec

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$ 1,076Multiple Airlines

Thu, 3 Dec - Sun, 6 Dec

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$ 1,092Air Canada

Fri, 6 Nov - Sun, 8 Nov

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$ 1,143Air Canada

Fri, 9 Oct - Sun, 11 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$ 1,291Lufthansa

Wed, 21 Oct - Fri, 23 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$ 1,546Multiple Airlines

Sun, 18 Oct - Sat, 24 Oct

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Porter Airlines flights from Manitoba to Chicago

Our best Porter Airlines deals on Manitoba to Chicago flight tickets

Porter Airlines

5 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD2:37 p.m.Chicago O'Hare Intl

12 Nov

ORD2:50 p.m.Chicago O'Hare Intl

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

C$ 740

Porter Airlines

18 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD2:37 p.m.Chicago O'Hare Intl

22 Nov

ORD2:50 p.m.Chicago O'Hare Intl

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

C$ 759

Porter Airlines

3 Dec

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD2:37 p.m.Chicago O'Hare Intl

6 Dec

ORD2:50 p.m.Chicago O'Hare Intl

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

C$ 761

WestJet flights from Manitoba to Chicago

Our best WestJet deals on Manitoba to Chicago 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$ 452

WestJet

19 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

23 Oct

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

16h 05m

2 stops

YWG9:35 a.m.Winnipeg

C$ 469

WestJet

19 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

23 Oct

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

17h 40m

1 stop

YWG11:10 a.m.Winnipeg

C$ 487

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$ 452

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

Fri 23/10

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

2 stops16h 05m

C$ 469

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

Fri 23/10

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

1 stop17h 40m

C$ 487

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

Sun 25/10

6:20 p.m.-2:20 p.m.

2 stops20h 00m

C$ 493

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

Sun 25/10

12:20 p.m.-9:15 a.m.

1 stop20h 55m

C$ 499

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

Mon 26/10

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

1 stop14h 55m

C$ 499

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 21/10

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

1 stop8h 23m

Chicago O'Hare Intl

Wed 28/10

4:30 p.m.-11:59 p.m.

1 stop7h 29m

C$ 727

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/11

5:15 a.m.-1:13 p.m.

1 stop7h 58m

Chicago O'Hare Intl

Tue 17/11

4:30 p.m.-11:44 p.m.

1 stop7h 14m

C$ 734

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 19/10

3:20 p.m.-7:59 a.m.

2 stops16h 39m

Chicago O'Hare Intl

Mon 26/10

8:01 p.m.-11:49 a.m.

2 stops15h 48m

C$ 879

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/10

3:20 p.m.-9:00 a.m.

2 stops17h 40m

Chicago O'Hare Intl

Tue 13/10

9:24 p.m.-11:12 a.m.

2 stops13h 48m

C$ 933

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 Manitoba to Chicago

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 cheapest month to fly to Chicago?

The month of February is another great option to travel to Chicago, with average flight prices from Manitoba averaging around C$ 737.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as C$ 865. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 1,167. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the morning is the cheapest time of day to fly from Manitoba to Chicago when you can find flight prices for as low as C$ 901. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,003 per ticket.

What is the cheapest Manitoba to Chicago flight route?

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

What cabin class options are available on Manitoba to Chicago flights?

There are 4 cabin classes available to choose from on Manitoba to Chicago 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 Manitoba to Chicago flights?

You could potentially save up to 38% on your flight if you consider stops on a Manitoba to Chicago flight.

Cheap Manitoba to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Manitoba to Chicago

Best price found	C$ 285
Fastest flight time	2h 31m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Manitoba in the past 72 hours is C$ 285. The best round-trip flight deal from Manitoba to Chicago found on momondo in the last 72 hours is C$ 452.

The fastest flight from Manitoba to Chicago takes 2h 31m

Direct flights go from Manitoba to Chicago every day.

There are 3 airports in Chicago. From Manitoba there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Manitoba to Chicago

When did momondo last update prices for flights from Manitoba to Chicago?
Prices for flights from Manitoba to Chicago refresh daily.
How many operators does momondo search for flights from Manitoba to Chicago?
There are 3 operators available for flights from Manitoba to Chicago as of September 2026.
How old do you have to be to fly from Manitoba to Chicago?
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 Manitoba to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Manitoba to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Manitoba to Chicago is Embraer 175 (Enhanced Winglets), representing 85.37% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 6.50%, Boeing 737 MAX 8 at 3.25%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 1.63%.

Best airlines flying from Manitoba to Chicago

Compare and see reviews for airlines that fly from Manitoba to Chicago with momondo

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom C$ 276	Free Cancellation	Rating 7.2 3,448 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 699	Free Cancellation	Rating 7.4 10,233 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 717	Free Cancellation	Rating 7.1 11,676 reviews	Search Air Canada flights

Merrillville

Benton Harbor

Hammond

Munster

Valparaiso

Portage

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Manitoba to Chicago for you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Manitoba with this policy.

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

momondo helps you find the best flight between Manitoba and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Manitoba and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Manitoba to Chicago from C$ 285

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Manitoba to Chicago departing on 26/10. 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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Big names, great deals

Filter for what you want

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Porter Airlines flights from Manitoba to Chicago

Our best Porter Airlines deals on Manitoba to Chicago flight tickets

WestJet flights from Manitoba to Chicago

Our best WestJet deals on Manitoba to Chicago flight tickets

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Use the filters below to find and compare flights from Manitoba to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Manitoba to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Manitoba to Chicago flight route?

What cabin class options are available on Manitoba to Chicago flights?

Can stopping save me money on Manitoba to Chicago flights?

What is the cheapest airline that flies from Manitoba to Chicago?

Which airlines fly to Chicago?

How many flights depart from Manitoba to Chicago on average per day?

How many flights depart from Manitoba to Chicago on average per week?

Cheap Manitoba to Chicago flight deals and tips

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Manitoba to Chicago

Best airlines flying from Manitoba to Chicago

Compare and see reviews for airlines that fly from Manitoba to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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