Which airlines fly to Chicago?

Air Canada, Porter Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Montreal according to our data. Air Canada is the first choice among our users, with 68% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Air Canada, Porter Airlines, and American Airlines are the most popular carriers operating from Montreal to Chicago

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

As of November 2025, 18 flights take off from Montreal and land in Chicago each day. The most common flight departure time for this route is 6:00a.m., with 54% of daily flights taking off in the afternoon.

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

As of November 2025, 128 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

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

Prices for flights from Montreal to Chicago were last updated today.

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

As of November 2025, there are 4 operators available to choose from for flights from Montreal to Chicago.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Montreal to Chicago.

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

The necessary travel and health documents for your Chicago 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$ 196 Cheap Flights from Montreal to Chicago in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:25 a.m. - 3:20 p.m.YUL-MDW

4h 55m1 stop

11:00 a.m. - 4:30 p.m.MDW-YUL

4h 30m1 stop

C$ 354Porter Airlines

Find Deal

Sun, 22 Mar - Mon, 30 Mar

9:25 a.m. - 11:18 a.m.YUL-ORD

2h 53mdirect

2:00 p.m. - 9:51 p.m.ORD-YUL

6h 51m1 stop

C$ 356Air Canada

Find Deal

Sun, 22 Mar - Mon, 30 Mar

6:25 p.m. - 8:10 p.m.YUL-ORD

2h 45mdirect

3:35 p.m. - 6:40 p.m.ORD-YUL

2h 05mdirect

C$ 357Air Canada

Find Deal

Mon, 19 Jan - Wed, 21 Jan

11:25 a.m. - 3:20 p.m.YUL-MDW

4h 55m1 stop

11:00 a.m. - 4:30 p.m.MDW-YUL

4h 30m1 stop

C$ 357Porter Airlines

Find Deal

Sun, 22 Mar - Mon, 30 Mar

7:00 a.m. - 4:39 p.m.YUL-ORD

10h 39m1 stop

5:50 a.m. - 5:04 p.m.ORD-YUL

10h 14m1 stop

C$ 358Delta

Find Deal

Sat, 4 Apr - Tue, 7 Apr

11:25 a.m. - 3:20 p.m.YUL-MDW

4h 55m1 stop

11:00 a.m. - 6:45 p.m.MDW-YUL

6h 45m1 stop

C$ 358Porter Airlines

Find Deal

Sun, 22 Mar - Mon, 30 Mar

7:00 a.m. - 4:39 p.m.YUL-ORD

10h 39m1 stop

7:10 a.m. - 5:04 p.m.ORD-YUL

8h 54m1 stop

C$ 360Delta

Find Deal

Sat, 4 Apr - Wed, 8 Apr

3:50 p.m. - 5:50 p.m.YUL-ORD

3h 00mdirect

8:50 p.m. - 12:20 p.m.ORD-YUL

14h 30m1 stop

C$ 399American Airlines

Find Deal

Thu, 4 Dec - Sat, 6 Dec

3:49 p.m. - 5:49 p.m.YUL-ORD

3h 00mdirect

6:48 a.m. - 12:15 p.m.ORD-YUL

4h 27m1 stop

C$ 418American Airlines

Find Deal

Fri, 28 Nov - Tue, 2 Dec

7:00 a.m. - 6:08 p.m.YUL-MDW

12h 08m1 stop

10:35 a.m. - 5:04 p.m.MDW-YUL

5h 29m1 stop

C$ 471WestJet

Find Deal

Fri, 13 Mar - Sun, 15 Mar

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets

Air Canada

22 Mar

YUL9:25 a.m.Montreal Pierre Elliott Trudeau Intl

2h 53m

ORD11:18 a.m.Chicago O'Hare Intl

30 Mar

ORD2:00 p.m.Chicago O'Hare Intl

6h 51m

1 stop

YUL9:51 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 356

Find similar

Air Canada

19 Jan

YUL6:25 p.m.Montreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:10 p.m.Chicago O'Hare Intl

21 Jan

ORD3:35 p.m.Chicago O'Hare Intl

2h 05m

YUL6:40 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 357

Find similar

Air Canada

4 Apr

YUL8:30 a.m.Montreal Pierre Elliott Trudeau Intl

2h 38m

ORD10:08 a.m.Chicago O'Hare Intl

11 Apr

ORD8:40 a.m.Chicago O'Hare Intl

2h 11m

YUL11:51 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 361

Find similar

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets

United Airlines

15 Nov

YUL4:45 p.m.Montreal Pierre Elliott Trudeau Intl

3h 00m

ORD6:45 p.m.Chicago O'Hare Intl

25 Dec

ORD5:52 p.m.Chicago O'Hare Intl

2h 25m

YUL9:17 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 676

Find similar

United Airlines

14 Nov

YUL2:13 p.m.Montreal Pierre Elliott Trudeau Intl

8h 25m

1 stop

ORD9:38 p.m.Chicago O'Hare Intl

25 Dec

ORD5:52 p.m.Chicago O'Hare Intl

2h 25m

YUL9:17 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 684

Find similar

United Airlines

15 Nov

YUL10:50 a.m.Montreal Pierre Elliott Trudeau Intl

13h 53m

2 stops

ORD11:43 p.m.Chicago O'Hare Intl

29 Dec

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

9h 30m

1 stop

YUL7:45 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 728

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 22/3

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Mon 30/3

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 354

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 22/3

9:25 a.m.-11:18 a.m.

Nonstop2h 53m

Chicago O'Hare Intl

Mon 30/3

2:00 p.m.-9:51 p.m.

1 stop6h 51m

C$ 356

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 19/1

6:25 p.m.-8:10 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Wed 21/1

3:35 p.m.-6:40 p.m.

Nonstop2h 05m

C$ 357

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 22/3

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Mon 30/3

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 357

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

7:00 a.m.-4:39 p.m.

1 stop10h 39m

Chicago O'Hare Intl

Tue 7/4

5:50 a.m.-5:04 p.m.

1 stop10h 14m

C$ 358

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 22/3

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Mon 30/3

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 358

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

7:00 a.m.-4:39 p.m.

1 stop10h 39m

Chicago O'Hare Intl

Wed 8/4

7:10 a.m.-5:04 p.m.

1 stop8h 54m

C$ 360

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 4/12

3:50 p.m.-5:50 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Sat 6/12

8:50 p.m.-12:20 p.m.

1 stop14h 30m

C$ 399

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 28/11

3:49 p.m.-5:49 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Tue 2/12

6:48 a.m.-12:15 p.m.

1 stop4h 27m

C$ 418

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 13/3

7:00 a.m.-6:08 p.m.

1 stop12h 08m

Chicago Midway

Sun 15/3

10:35 a.m.-5:04 p.m.

1 stop5h 29m

C$ 471

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How to get the cheapest flight ticket from Montreal 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 typical price of a round-trip flight between Montreal and Chicago?

What is the cheapest month to fly to Chicago?

The month of March is another great option to travel to Chicago, with average flight prices from Montreal averaging around C$ 402.

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 Thursday when prices can be found for as low as C$ 729. 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 Sunday because tickets tend to average around C$ 1,010. 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 afternoon is the cheapest time of day to fly from Montreal to Chicago when you can find flight prices for as low as C$ 758. Flying to Chicago in the afternoon 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$ 1,055 per ticket.

What is the cheapest Montreal to Chicago flight route?

Fly from Montreal Pierre Elliott Trudeau Intl to Chicago O'Hare Intl for the best Montreal - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Montreal when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 525 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Montreal for as low as C$ 326 on momondo.

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

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

You could potentially save up to 8% on your flight if you consider stops on a Montreal to Chicago flight.

How have Montreal to Chicago flight prices changed over time?

As of November 2025, prices for Montreal to Chicago flights are approximately 4% cheaper when compared to flights at the same time last year.

When to book flights from Montreal to Chicago

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

Estimated round-trip price

Cheap Montreal to Chicago (YMQ to CHI) flight deals and tips

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

Best price found	C$ 308
Fastest flight time	2h 35m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Montreal in the past 72 hours is C$ 308. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is C$ 610.

The fastest flight from Montreal to Chicago takes 2h 35m

Direct flights go from Montreal to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Montreal to Chicago by plane?
There are 1197.7 km between Montreal and Chicago. 2h 35m is a normal flight duration for this route.
When did momondo last update prices for flights from Montreal to Chicago?
Prices for flights from Montreal to Chicago were last updated today.
How many operators does momondo search for flights from Montreal to Chicago?
As of November 2025, there are 4 operators available to choose from for flights from Montreal to Chicago.
How old do you have to be to fly from Montreal to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Montreal to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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 Montreal to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Montreal to Chicago is Embraer 175 (Enhanced Winglets), representing 29.46% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet 900 at 11.16%, Boeing 737 MAX 8 at 11.02%, and Embraer 175 at 11.02%.
What is the most popular airline from Montreal to Chicago?
Based on momondo bookings for flights between Montreal and Chicago, the leading airline is Air Canada, making up 61% of the total bookings. Other popular airlines include Porter Airlines with 30%, United Airlines with 4%, and WestJet with 3%.

Best airlines flying from Montreal to Chicago

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

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 201	Free Cancellation	Rating 8.0 387 reviews	Search Porter Airlines flights
American Airlines	PriceFrom C$ 207	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
Air Canada	PriceFrom C$ 264	Free Cancellation	Rating 7.1 10,415 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 276	Free Cancellation	Rating 7.4 9,004 reviews	Search United Airlines flights

Porter Airlines Flights From Montreal to Chicago
Porter Airlines flies from Montreal to Chicago around 4 times per week, with 387 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Montreal to Chicago in the last 72 hours was C$ 201 (round-trip), much lower than the average airfare cost of C$ 543 for Porter Airlines flights on this route.
United Airlines Flights From Montreal to Chicago
United Airlines (7.4/10 from 9,004 reviews) operates around 35 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around C$ 510, with deals from around C$ 276 rare but found on momondo. Referenced prices are for round-trip Montreal to Chicago flight searches in the last 72 hours.

Munster

Hammond

Merrillville

Why use momondo?

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

It is quick and easy to find Montreal to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. All flights to Chicago from Montreal on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Chicago from Montreal. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Montreal are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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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Sat 13/12

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Cheap flights from Montreal to Chicago from C$ 230

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montreal to Chicago departing on 2/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Montreal to Chicago

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Cheap last-minute flights

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Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Montreal 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

What is the typical price of a round-trip flight between Montreal and Chicago?

What is the cheapest month to fly to Chicago?

The month of March is another great option to travel to Chicago, with average flight prices from Montreal averaging around C$ 402.

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 Montreal to Chicago flight route?

Fly from Montreal Pierre Elliott Trudeau Intl to Chicago O'Hare Intl for the best Montreal - Chicago flight prices

How far in advance should I book a flight to Chicago?

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

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

You could potentially save up to 8% on your flight if you consider stops on a Montreal to Chicago flight.

How have Montreal to Chicago flight prices changed over time?

As of November 2025, prices for Montreal to Chicago flights are approximately 4% cheaper when compared to flights at the same time last year.

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

Air Canada, Porter Airlines, and American Airlines are the most popular carriers operating from Montreal to Chicago

Which airlines fly to Chicago?

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

As of November 2025, 18 flights take off from Montreal and land in Chicago each day. The most common flight departure time for this route is 6:00a.m., with 54% of daily flights taking off in the afternoon.

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

As of November 2025, 128 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

When to book flights from Montreal to Chicago

Cheap Montreal to Chicago (YMQ to CHI) flight deals and tips

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

Best price found

Fastest flight time

Direct flights

Airports in Chicago

How far is Montreal to Chicago by plane?

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

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

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

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

What is the most popular plane model from Montreal to Chicago?

What is the most popular airline from Montreal to Chicago?

Best airlines flying from Montreal to Chicago

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

Porter Airlines Flights From Montreal to Chicago

United Airlines Flights From Montreal to Chicago

Travelling to a place near Chicago?

Why use momondo?

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

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

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

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

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