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 (YTZ) has the shortest average layover time for this route: 1h 27m.

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 is the cheapest airline that flies from Montreal to Chicago?

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

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.

What airlines fly to Chicago?

Air Canada, United Airlines and Porter 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 73% 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?

18 flights are operational daily from Montreal to Chicago as of November 2025. The most popular departure time for this route is 6:00AM, with 54% of flights per day taking off in the afternoon.

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

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

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 November 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

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

Prices are currently low for flights on this route. Typical prices usually range from $276 to $687. The lowest price recently found on this route was $231.

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One-way

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Cheap round-trip flights

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2:10 pm - 5:48 pmYUL-ORD

4h 38m1 stop

12:50 pm - 3:57 pmORD-YUL

2h 07mnonstop

$231Air Canada

Find Deal

Tue, Feb 24 - Tue, Mar 3

10:10 am - 3:10 pmYUL-ORD

6h 00m1 stop

3:35 pm - 6:40 pmORD-YUL

2h 05mnonstop

$232Air Canada

Find Deal

Sat, Jan 24 - Wed, Jan 28

10:15 am - 3:20 pmYUL-MDW

6h 05m1 stop

11:00 am - 6:45 pmMDW-YUL

6h 45m1 stop

$233Porter Airlines

Find Deal

Thu, Apr 2 - Tue, Apr 7

6:00 am - 9:35 amYUL-ORD

4h 35m1 stop

7:10 am - 5:04 pmORD-YUL

8h 54m1 stop

$233Delta

Find Deal

Sat, Apr 4 - Wed, Apr 8

4:45 pm - 6:45 pmYUL-ORD

3h 00mnonstop

12:50 pm - 3:57 pmORD-YUL

2h 07mnonstop

$237Multiple Airlines

Find Deal

Tue, Feb 24 - Tue, Mar 3

2:25 pm - 11:35 amYUL-ORD

22h 10m1 stop

8:09 am - 3:20 pmORD-YUL

6h 11m1 stop

$243American Airlines

Find Deal

Thu, Feb 5 - Sun, Feb 8

8:55 am - 11:50 amYUL-MDW

3h 55m1 stop

11:00 am - 5:45 pmMDW-YUL

5h 45m1 stop

$247Porter Airlines

Find Deal

Sat, Apr 4 - Tue, Apr 7

7:30 pm - 9:58 amYUL-MDW

15h 28m2 stops

11:00 am - 6:15 pmMDW-YUL

6h 15m1 stop

$251Multiple Airlines

Find Deal

Tue, Feb 24 - Tue, Mar 3

6:00 am - 9:35 amYUL-ORD

4h 35m1 stop

5:50 am - 5:04 pmORD-YUL

10h 14m1 stop

$255Delta

Find Deal

Sat, Apr 4 - Wed, Apr 8

2:25 pm - 7:40 pmYUL-ORD

6h 15m1 stop

8:55 pm - 3:24 pmORD-YUL

17h 29m1 stop

$301American Airlines

Find Deal

Tue, Feb 24 - Tue, Mar 3

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets

Air Canada

Feb 24

YUL2:10 pmMontreal Pierre Elliott Trudeau Intl

4h 38m

1 stop

ORD5:48 pmChicago O'Hare Intl

Mar 3

ORD12:50 pmChicago O'Hare Intl

2h 07m

YUL3:57 pmMontreal Pierre Elliott Trudeau Intl

$231

Find similar

Air Canada

Jan 24

YUL10:10 amMontreal Pierre Elliott Trudeau Intl

6h 00m

1 stop

ORD3:10 pmChicago O'Hare Intl

Jan 28

ORD3:35 pmChicago O'Hare Intl

2h 05m

YUL6:40 pmMontreal Pierre Elliott Trudeau Intl

$232

Find similar

Air Canada

Jan 22

YUL4:45 pmMontreal Pierre Elliott Trudeau Intl

3h 06m

ORD6:51 pmChicago O'Hare Intl

Jan 26

ORD10:35 amChicago O'Hare Intl

2h 25m

YUL2:00 pmMontreal Pierre Elliott Trudeau Intl

$239

Find similar

Delta flights from Montreal to Chicago

Our best Delta deals on Montreal to Chicago flight tickets

Delta

Apr 4

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

4h 35m

1 stop

ORD9:35 amChicago O'Hare Intl

Apr 8

ORD7:10 amChicago O'Hare Intl

8h 54m

1 stop

YUL5:04 pmMontreal Pierre Elliott Trudeau Intl

$233

Find similar

Delta

Apr 4

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

4h 35m

1 stop

ORD9:35 amChicago O'Hare Intl

Apr 8

ORD5:50 amChicago O'Hare Intl

10h 14m

1 stop

YUL5:04 pmMontreal Pierre Elliott Trudeau Intl

$255

Find similar

Delta

Nov 23

YUL7:10 amMontreal Pierre Elliott Trudeau Intl

5h 24m

1 stop

ORD11:34 amChicago O'Hare Intl

Nov 28

ORD6:45 amChicago O'Hare Intl

4h 15m

1 stop

YUL12:00 pmMontreal Pierre Elliott Trudeau Intl

$302

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

2:10 pm-5:48 pm

1 stop4h 38m

Chicago O'Hare Intl

Tue 3/3

12:50 pm-3:57 pm

Nonstop2h 07m

$231

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 1/24

10:10 am-3:10 pm

1 stop6h 00m

Chicago O'Hare Intl

Wed 1/28

3:35 pm-6:40 pm

Nonstop2h 05m

$232

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 4/2

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Tue 4/7

11:00 am-6:45 pm

1 stop6h 45m

$233

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

6:00 am-9:35 am

1 stop4h 35m

Chicago O'Hare Intl

Wed 4/8

7:10 am-5:04 pm

1 stop8h 54m

$233

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

4:45 pm-6:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 3/3

12:50 pm-3:57 pm

Nonstop2h 07m

$237

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 2/5

2:25 pm-11:35 am

1 stop22h 10m

Chicago O'Hare Intl

Sun 2/8

8:09 am-3:20 pm

1 stop6h 11m

$243

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

8:55 am-11:50 am

1 stop3h 55m

Chicago Midway

Tue 4/7

11:00 am-5:45 pm

1 stop5h 45m

$247

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

7:30 pm-9:58 am

2 stops15h 28m

Chicago Midway

Tue 3/3

11:00 am-6:15 pm

1 stop6h 15m

$251

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

6:00 am-9:35 am

1 stop4h 35m

Chicago O'Hare Intl

Wed 4/8

5:50 am-5:04 pm

1 stop10h 14m

$255

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

2:25 pm-7:40 pm

1 stop6h 15m

Chicago O'Hare Intl

Tue 3/3

8:55 pm-3:24 pm

1 stop17h 29m

$301

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Showing 1-10 of 20 resultsSorted by cheapest first

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 September is, on average, the cheapest month to fly to Chicago from Montreal, with most prices found around $282. If you’re not able to fly to Chicago in September, then March is your next best option. Flight prices from Montreal to Chicago during March average around $285.

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 Friday when prices can be found for as low as $446. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Montreal to Chicago for around $630.

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 $475. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $528.

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 $372 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 $231 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 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	$239
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 $239. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is $333.

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?
Montreal and Chicago are 744.2 mi apart from one another. 2h 41m 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 November 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) (28.67% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (12.79%), Embraer 175 (10.96%), and Canadair (Bombardier) Regional Jet 900 (10.05%).
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 (26%) and United Airlines (7%).

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
Air Canada	PriceFrom $174	Free Cancellation	Rating 7.1 10,397 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $226	Free Cancellation	Rating 8.0 384 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $251	Free Cancellation	Rating 7.2 11,034 reviews	Search American Airlines flights
United Airlines	PriceFrom $267	Free Cancellation	Rating 7.4 8,996 reviews	Search United Airlines flights

Porter Airlines Flights From Montreal to Chicago
Porter Airlines flight deals from Montreal to Chicago start from $226 round-trip. Over the 4 Porter Airlines flights for this route in a normal week, average airfare is usually $325 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Montreal to Chicago
United Airlines (7.4/10 from 8,996 reviews) operates around 35 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around $402, with deals from around $267 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

Portage

Lansing

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 $165

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 12/3. 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 Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets

Delta flights from Montreal to Chicago

Our best Delta 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 September is, on average, the cheapest month to fly to Chicago from Montreal, with most prices found around $282. If you’re not able to fly to Chicago in September, then March is your next best option. Flight prices from Montreal to Chicago during March average around $285.

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 $475. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $528.

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 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 Delta 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 (YTZ) has the shortest average layover time for this route: 1h 27m.

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

18 flights are operational daily from Montreal to Chicago as of November 2025. The most popular departure time for this route is 6:00AM, with 54% of flights per day 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

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.