Which layover airport has the shortest travel time from Montreal to Chicago?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 4h 49m.

Which airport is the most popular layover for flights between Montreal and Chicago?

Toronto (YTZ) was the most common stop: 93% of momondo users choosing 1-stop flights on this route connected there.

What airlines fly to Chicago?

Air Canada, United Airlines and American 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 70% of people opting to fly with this airline when traveling 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.

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

30 flights are operational daily from Montreal to Chicago as of September 2025. The most popular departure time for this route is 6:00AM, with 47% of flights per day taking off in the afternoon.

Which layover airport has the shortest connection time from Montreal to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 1h 53m.

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

As of September 2025, 215 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.

Which layover airport offers the lowest fares from Montreal to Chicago?

Flights via Toronto (YYZ) offer the lowest average round-trip price of $279.

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

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

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

Prices for flights from Montreal to Chicago refresh daily.

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

The number of operators available for flights from Montreal to Chicago is 4 as of September 2025.

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 offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify 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.

$142 Cheap Flights from Montreal to Chicago in 2025/26

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Find the cheapest flights from Montreal to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

1:10 pm - 4:24 pmYUL-MDW

4h 14m1 stop

9:35 am - 4:00 pmMDW-YUL

5h 25m1 stop

$234Porter Airlines

Find Deal

Fri, Oct 17 - Mon, Oct 20

1:10 pm - 4:24 pmYUL-MDW

4h 14m1 stop

9:35 am - 4:00 pmMDW-YUL

5h 25m1 stop

$235Porter Airlines

Find Deal

Fri, Oct 17 - Mon, Oct 20

6:15 pm - 8:00 pmYUL-ORD

2h 45mnonstop

7:15 am - 10:20 amORD-YUL

2h 05mnonstop

$241Air Canada

Find Deal

Wed, Oct 29 - Wed, Nov 5

9:10 am - 1:01 pmYUL-ORD

4h 51m1 stop

12:50 pm - 3:57 pmORD-YUL

2h 07mnonstop

$249Air Canada

Find Deal

Wed, Oct 29 - Wed, Nov 5

6:00 am - 8:00 amYUL-ORD

3h 00mnonstop

5:55 pm - 9:17 pmORD-YUL

2h 22mnonstop

$260United Airlines

Find Deal

Fri, Nov 21 - Sat, Nov 29

9:45 am - 11:23 amYUL-ORD

2h 38mnonstop

4:00 pm - 10:06 pmORD-YUL

5h 06m1 stop

$270United Airlines

Find Deal

Tue, Oct 7 - Tue, Oct 7

6:00 am - 10:01 amYUL-ORD

5h 01m1 stop

6:45 am - 11:59 amORD-YUL

4h 14m1 stop

$285Delta

Find Deal

Sat, Nov 22 - Sat, Nov 29

9:45 am - 11:23 amYUL-ORD

2h 38mnonstop

8:40 am - 11:54 amORD-YUL

2h 14mnonstop

$288Multiple Airlines

Find Deal

Thu, Oct 16 - Sun, Oct 19

6:00 am - 12:28 pmYUL-MDW

7h 28m1 stop

4:23 pm - 11:48 pmMDW-YUL

6h 25m1 stop

$289Delta

Find Deal

Sun, Oct 12 - Sat, Oct 25

2:20 pm - 11:15 pmYUL-ORD

9h 55m1 stop

9:55 am - 4:20 pmORD-YUL

5h 25m1 stop

$296Multiple Airlines

Find Deal

Thu, Oct 16 - Sun, Oct 19

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets

Air Canada

Oct 29

YUL6:15 pmMontreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:00 pmChicago O'Hare Intl

Nov 5

ORD7:15 amChicago O'Hare Intl

2h 05m

YUL10:20 amMontreal Pierre Elliott Trudeau Intl

$241

Find similar

Air Canada

Oct 29

YUL9:10 amMontreal Pierre Elliott Trudeau Intl

4h 51m

1 stop

ORD1:01 pmChicago O'Hare Intl

Nov 5

ORD12:50 pmChicago O'Hare Intl

2h 07m

YUL3:57 pmMontreal Pierre Elliott Trudeau Intl

$249

Find similar

Air Canada

Oct 29

YUL6:15 pmMontreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:00 pmChicago O'Hare Intl

Nov 5

ORD2:00 pmChicago O'Hare Intl

5h 44m

2 stops

YUL8:44 pmMontreal Pierre Elliott Trudeau Intl

$250

Find similar

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets

United Airlines

Nov 21

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

3h 00m

ORD8:00 amChicago O'Hare Intl

Nov 29

ORD5:55 pmChicago O'Hare Intl

2h 22m

YUL9:17 pmMontreal Pierre Elliott Trudeau Intl

$260

Find similar

United Airlines

Oct 7

YUL9:45 amMontreal Pierre Elliott Trudeau Intl

2h 38m

ORD11:23 amChicago O'Hare Intl

Oct 7

ORD4:00 pmChicago O'Hare Intl

5h 06m

1 stop

YUL10:06 pmMontreal Pierre Elliott Trudeau Intl

$270

Find similar

United Airlines

Oct 16

YUL2:20 pmMontreal Pierre Elliott Trudeau Intl

9h 55m

1 stop

ORD11:15 pmChicago O'Hare Intl

Oct 19

ORD2:08 pmChicago O'Hare Intl

2h 18m

YUL5:26 pmMontreal Pierre Elliott Trudeau Intl

$278

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Mon 10/20

9:35 am-4:00 pm

1 stop5h 25m

$234

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Mon 10/20

9:35 am-4:00 pm

1 stop5h 25m

$235

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 10/29

6:15 pm-8:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 11/5

7:15 am-10:20 am

Nonstop2h 05m

$241

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 10/29

9:10 am-1:01 pm

1 stop4h 51m

Chicago O'Hare Intl

Wed 11/5

12:50 pm-3:57 pm

Nonstop2h 07m

$249

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 11/21

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 11/29

5:55 pm-9:17 pm

Nonstop2h 22m

$260

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 10/7

9:45 am-11:23 am

Nonstop2h 38m

Chicago O'Hare Intl

Tue 10/7

4:00 pm-10:06 pm

1 stop5h 06m

$270

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 11/22

6:00 am-10:01 am

1 stop5h 01m

Chicago O'Hare Intl

Sat 11/29

6:45 am-11:59 am

1 stop4h 14m

$285

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 10/16

9:45 am-11:23 am

Nonstop2h 38m

Chicago O'Hare Intl

Sun 10/19

8:40 am-11:54 am

Nonstop2h 14m

$288

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 10/12

6:00 am-12:28 pm

1 stop7h 28m

Chicago Midway

Sat 10/25

4:23 pm-11:48 pm

1 stop6h 25m

$289

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 10/16

2:20 pm-11:15 pm

1 stop9h 55m

Chicago O'Hare Intl

Sun 10/19

9:55 am-4:20 pm

1 stop5h 25m

$296

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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

Layovers

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, on average, the cheapest month to fly to Chicago from Montreal, with most prices found around $288. If you’re not able to fly to Chicago in March, then June is your next best option. Flight prices from Montreal to Chicago during June average around $301.

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 $469. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Montreal to Chicago for around $628.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Montreal to Chicago during this time can be as low as $494. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $548.

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 $382 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 $210 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?

No. A direct flight is the cheapest option for a flight between Montreal to Chicago.

How have Montreal to Chicago flight prices changed over time?

As of September 2025, prices for Montreal to Chicago flights are approximately 20% 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	$276
Fastest flight time	2h 31m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Montreal in the past 72 hours is $276. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is $391.

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

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?
Montreal and Chicago are 744.2 mi apart from one another. 2h 31m 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 refresh daily.
How many operators does momondo search for flights from Montreal to Chicago?
The number of operators available for flights from Montreal to Chicago is 4 as of September 2025.
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 offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Montreal to Chicago is Embraer 175 (Enhanced Winglets) (26.32% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (15.69%), Embraer 175 (14.78%), and Airbus A321-100/200 (10.78%).
What is the most popular airline from Montreal to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Montreal to Chicago is Air Canada (67% of total bookings). The next most popular airlines are Porter Airlines (28%) and United Airlines (5%).

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
United Airlines	PriceFrom $112	Free Cancellation	Rating 7.4 8,929 reviews	Search United Airlines flights
Air Canada	PriceFrom $178	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $226	Free Cancellation	Rating 7.9 363 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $262	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

United Airlines Flights From Montreal to Chicago
United Airlines flight deals from Montreal to Chicago start from $112 round-trip. Over the 41 United Airlines flights for this route in a normal week, average airfare is usually $487 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Montreal to Chicago
American Airlines (7.2/10 from 10,000 reviews) operates around 14 flights from Montreal to Chicago in any given week. The average American Airlines airfare for this route is around $407, with deals from around $262 rare but found on momondo. Referenced prices are for round-trip Montreal to Chicago flight searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Montreal.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Montreal.

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.

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Cheap flights from Montreal to Chicago from $142

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 10/30. 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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Find the cheapest flights from Montreal to Chicago

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

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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

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, on average, the cheapest month to fly to Chicago from Montreal, with most prices found around $288. If you’re not able to fly to Chicago in March, then June is your next best option. Flight prices from Montreal to Chicago during June average around $301.

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?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Montreal to Chicago during this time can be as low as $494. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $548.

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?

No. A direct flight is the cheapest option for a flight between Montreal to Chicago.

How have Montreal to Chicago flight prices changed over time?

As of September 2025, prices for Montreal to Chicago flights are approximately 20% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Montreal and Chicago?

Toronto (YTZ) was the most common stop: 93% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Montreal to Chicago?

Flights via Toronto (YYZ) offer the lowest average round-trip price of $279.

Which layover airport has the shortest travel time from Montreal to Chicago?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 4h 49m.

Which layover airport has the shortest connection time from Montreal to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 1h 53m.

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

30 flights are operational daily from Montreal to Chicago as of September 2025. The most popular departure time for this route is 6:00AM, with 47% of flights per day taking off in the afternoon.

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

As of September 2025, 215 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% 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

United Airlines Flights From Montreal to Chicago

American Airlines Flights From Montreal to Chicago

Traveling 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.