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 airlines fly to Chicago?

Air Canada, American 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 69% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 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

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 July 2025. The most popular departure time for this route is 6:00AM, with 48% of flights per day taking off in the afternoon.

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.

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

As of July 2025, 211 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Wed, with 15% of weekly flights taking off on this day.

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.

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 5 as of July 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.

$107 Cheap Flights from Montreal to Chicago in 2025

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Find the cheapest flights from Montreal to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:20 am - 9:51 amYUL-ORD

2h 31mnonstop

10:40 am - 1:54 pmORD-YUL

2h 14mnonstop

$175Air Canada

Find Deal

Thu, Sep 18 - Sun, Sep 21

8:20 am - 9:51 amYUL-ORD

2h 31mnonstop

10:40 am - 1:54 pmORD-YUL

2h 14mnonstop

$186Air Canada

Find Deal

Fri, Oct 3 - Tue, Oct 7

10:45 am - 4:24 pmYUL-MDW

6h 39m1 stop

5:20 pm - 10:15 pmMDW-YUL

3h 55m1 stop

$198Porter Airlines

Find Deal

Fri, Oct 3 - Sun, Oct 5

1:10 pm - 4:24 pmYUL-MDW

4h 14m1 stop

5:20 pm - 10:15 pmMDW-YUL

3h 55m1 stop

$200Porter Airlines

Find Deal

Thu, Oct 2 - Fri, Oct 10

7:50 am - 12:20 pmYUL-ORD

5h 30m1 stop

7:00 am - 10:57 pmORD-YUL

14h 57m1 stop

$200American Airlines

Find Deal

Thu, Sep 4 - Sun, Sep 7

6:00 am - 1:09 pmYUL-ORD

8h 09m1 stop

10:30 am - 7:25 pmORD-YUL

7h 55m1 stop

$215Delta

Find Deal

Thu, Sep 4 - Sat, Sep 13

6:00 am - 8:35 amYUL-MDW

3h 35m1 stop

6:00 am - 1:38 pmMDW-YUL

6h 38m1 stop

$215Delta

Find Deal

Wed, Sep 3 - Sat, Sep 6

5:29 pm - 7:05 pmYUL-ORD

2h 36mnonstop

9:51 am - 10:32 pmORD-YUL

11h 41m1 stop

$220American Airlines

Find Deal

Sat, Aug 30 - Wed, Sep 3

9:45 am - 11:23 amYUL-ORD

2h 38mnonstop

6:00 pm - 9:29 pmORD-YUL

2h 29mnonstop

$261United Airlines

Find Deal

Sat, Aug 23 - Sat, Aug 30

6:15 am - 8:01 amYUL-ORD

2h 46mnonstop

2:08 pm - 5:26 pmORD-YUL

2h 18mnonstop

$262United Airlines

Find Deal

Thu, Aug 28 - Tue, Sep 2

American Airlines flights from Montreal to Chicago

Our best American Airlines deals on Montreal to Chicago flight tickets

American Airlines

Sep 4

YUL7:50 amMontreal Pierre Elliott Trudeau Intl

5h 30m

1 stop

ORD12:20 pmChicago O'Hare Intl

Sep 7

ORD7:00 amChicago O'Hare Intl

14h 57m

1 stop

YUL10:57 pmMontreal Pierre Elliott Trudeau Intl

$200

Find similar

American Airlines

Aug 30

YUL5:29 pmMontreal Pierre Elliott Trudeau Intl

2h 36m

ORD7:05 pmChicago O'Hare Intl

Sep 3

ORD9:51 amChicago O'Hare Intl

11h 41m

1 stop

YUL10:32 pmMontreal Pierre Elliott Trudeau Intl

$220

Find similar

American Airlines

Aug 28

YUL5:29 pmMontreal Pierre Elliott Trudeau Intl

2h 36m

ORD7:05 pmChicago O'Hare Intl

Sep 8

ORD7:00 amChicago O'Hare Intl

14h 57m

1 stop

YUL10:57 pmMontreal Pierre Elliott Trudeau Intl

$228

Find similar

Delta flights from Montreal to Chicago

Our best Delta deals on Montreal to Chicago flight tickets

Delta

Sep 4

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

8h 09m

1 stop

ORD1:09 pmChicago O'Hare Intl

Sep 13

ORD10:30 amChicago O'Hare Intl

7h 55m

1 stop

YUL7:25 pmMontreal Pierre Elliott Trudeau Intl

$215

Find similar

Delta

Sep 13

YUL7:00 amMontreal Pierre Elliott Trudeau Intl

9h 51m

1 stop

ORD3:51 pmChicago O'Hare Intl

Sep 20

ORD2:25 pmChicago O'Hare Intl

8h 04m

1 stop

YUL11:29 pmMontreal Pierre Elliott Trudeau Intl

$216

Find similar

Delta

Aug 30

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

7h 28m

1 stop

MDW12:28 pmChicago Midway

Sep 3

MDW1:43 pmChicago Midway

8h 33m

1 stop

YUL11:16 pmMontreal Pierre Elliott Trudeau Intl

$245

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/18

8:20 am-9:51 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/21

10:40 am-1:54 pm

Nonstop2h 14m

$175

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 10/3

8:20 am-9:51 am

Nonstop2h 31m

Chicago O'Hare Intl

Tue 10/7

10:40 am-1:54 pm

Nonstop2h 14m

$186

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/3

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 10/5

5:20 pm-10:15 pm

1 stop3h 55m

$198

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/2

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Fri 10/10

5:20 pm-10:15 pm

1 stop3h 55m

$200

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/4

7:50 am-12:20 pm

1 stop5h 30m

Chicago O'Hare Intl

Sun 9/7

7:00 am-10:57 pm

1 stop14h 57m

$200

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/4

6:00 am-1:09 pm

1 stop8h 09m

Chicago O'Hare Intl

Sat 9/13

10:30 am-7:25 pm

1 stop7h 55m

$215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/3

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Sat 9/6

6:00 am-1:38 pm

1 stop6h 38m

$215

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 8/30

5:29 pm-7:05 pm

Nonstop2h 36m

Chicago O'Hare Intl

Wed 9/3

9:51 am-10:32 pm

1 stop11h 41m

$220

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 8/23

9:45 am-11:23 am

Nonstop2h 38m

Chicago O'Hare Intl

Sat 8/30

6:00 pm-9:29 pm

Nonstop2h 29m

$261

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 8/28

6:15 am-8:01 am

Nonstop2h 46m

Chicago O'Hare Intl

Tue 9/2

2:08 pm-5:26 pm

Nonstop2h 18m

$262

Flights are sorted by cheapest round-trip flights first.

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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 $292. 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 Saturday when prices can be found for as low as $462. 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 $578.

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 $495. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $511.

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 $386 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?

You could potentially save up to 9% 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 July 2025, prices for Montreal to Chicago flights are approximately 19% 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	$107
Fastest flight time	2h 28m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Montreal in the past 72 hours is $107. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is $175.

The fastest flight from Montreal to Chicago takes 2h 28m

Direct flights go from Montreal to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Montreal to Chicago by plane?
Montreal and Chicago are 744.2 mi apart from one another. 2h 28m 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 5 as of July 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) (28.70% of total bookings). The next most popular plane models are Embraer 175 (18.00%), Boeing 737 MAX 8 (14.96%), and Airbus A321-100/200 (9.21%).
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 (63% of total bookings). The next most popular airlines are Porter Airlines (27%), American Airlines (5%), 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 8,900 reviews	Search United Airlines flights
Air Canada	PriceFrom $217	Free Cancellation	Rating 7.1 9,851 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $217	Free Cancellation	Rating 8.0 318 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $275	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
WestJet	PriceFrom $334	Free Cancellation	Rating 7.2 2,978 reviews	Search WestJet flights

United Airlines Flights From Montreal to Chicago
United Airlines flight deals from Montreal to Chicago start from $112 round-trip. Over the 38 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 13 flights from Montreal to Chicago in any given week. The average American Airlines airfare for this route is around $407, with deals from around $275 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 $107

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 11/1. 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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Filter for what you want

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Find the cheapest flights from Montreal to Chicago

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American Airlines flights from Montreal to Chicago

Our best American Airlines 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.

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, on average, the cheapest month to fly to Chicago from Montreal, with most prices found around $292. 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 $495. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $511.

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 9% 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 July 2025, prices for Montreal to Chicago flights are approximately 19% 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

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 July 2025. The most popular departure time for this route is 6:00AM, with 48% of flights per day taking off in the afternoon.

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

As of July 2025, 211 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Wed, with 15% 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.