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 Pierre Elliott Trudeau Intl Airport according to our data. Air Canada is the first choice among our users, with 75% of people opting to fly with this airline when traveling 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.

What is the cheapest airline that flies from Montreal Pierre Elliott Trudeau Intl to Chicago?

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

How old do you have to be to fly from Montreal Pierre Elliott Trudeau Intl Airport 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 Montreal Pierre Elliott Trudeau Intl Airport 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.

$166 Cheap Flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in 2026

Q: What is the typical price of a round-trip flight between Montreal Pierre Elliott Trudeau Intl Airport and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $314 to $484. The lowest price recently found on this route was $275.

Q: How many flights depart from Montreal Pierre Elliott Trudeau Intl Airport to Chicago on average per week?

216 flights are operational weekly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago as of July 2026. The most popular departure day for this route is Sat, with 15% of flights per week taking off on this day.

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Find the cheapest flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:50 am - 10:19 am

YUL

ORD

2h 29mnonstop

3:45 pm - 9:50 pm

ORD

YUL

5h 05m

1 stop

$275Air Canada

Sun, Aug 30 - Sun, Sep 6

6:30 am - 9:45 am

YUL

MDW

4h 15m

1 stop

10:25 am - 6:10 pm

MDW

YUL

6h 45m

1 stop

$275Porter Airlines

Mon, Aug 10 - Thu, Aug 20

10:35 am - 2:35 pm

YUL

MDW

5h 00m

1 stop

10:20 am - 6:10 pm

MDW

YUL

6h 50m

1 stop

$276Porter Airlines

Wed, Aug 5 - Sun, Aug 9

6:30 am - 9:45 am

YUL

MDW

4h 15m

1 stop

3:15 pm - 10:10 pm

MDW

YUL

5h 55m

1 stop

$277Porter Airlines

Tue, Aug 4 - Wed, Aug 5

6:30 pm - 8:05 pm

YUL

ORD

2h 35mnonstop

8:40 am - 11:59 am

ORD

YUL

2h 19mnonstop

$278Air Canada

Sat, Aug 22 - Sat, Aug 29

10:35 am - 2:35 pm

YUL

MDW

5h 00m

1 stop

10:20 am - 6:10 pm

MDW

YUL

6h 50m

1 stop

$278Porter Airlines

Thu, Aug 6 - Sun, Aug 9

8:40 am - 10:16 am

YUL

ORD

2h 36mnonstop

8:45 am - 12:00 pm

ORD

YUL

2h 15mnonstop

$279Air Canada

Wed, Jul 22 - Mon, Jul 27

10:35 am - 2:35 pm

YUL

MDW

5h 00m

1 stop

3:15 pm - 10:10 pm

MDW

YUL

5h 55m

1 stop

$279Porter Airlines

Wed, Jul 29 - Wed, Aug 5

12:30 pm - 2:10 pm

YUL

ORD

2h 40mnonstop

6:30 am - 10:56 pm

ORD

YUL

15h 26m

1 stop

$285American Airlines

Thu, Jul 30 - Mon, Aug 3

12:47 pm - 8:30 pm

YUL

ORD

8h 43m

1 stop

6:59 am - 11:56 am

ORD

YUL

3h 57m

1 stop

$286Delta

Thu, Aug 6 - Sun, Aug 9

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Air Canada flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Our best Air Canada deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight tickets

Air Canada

Aug 30

YUL8:50 amMontreal Pierre Elliott Trudeau Intl

2h 29m

ORD10:19 amChicago O'Hare Intl

Sep 6

ORD3:45 pmChicago O'Hare Intl

5h 05m

1 stop

YUL9:50 pmMontreal Pierre Elliott Trudeau Intl

$275

Air Canada

Aug 22

YUL6:30 pmMontreal Pierre Elliott Trudeau Intl

2h 35m

ORD8:05 pmChicago O'Hare Intl

Aug 29

ORD8:40 amChicago O'Hare Intl

2h 19m

YUL11:59 amMontreal Pierre Elliott Trudeau Intl

$278

Air Canada

Jul 22

YUL4:30 pmMontreal Pierre Elliott Trudeau Intl

4h 59m

1 stop

ORD8:29 pmChicago O'Hare Intl

Jul 29

ORD2:00 pmChicago O'Hare Intl

4h 47m

1 stop

YUL7:47 pmMontreal Pierre Elliott Trudeau Intl

$279

Porter Airlines flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Our best Porter Airlines deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight tickets

Porter Airlines

Aug 10

YUL6:30 amMontreal Pierre Elliott Trudeau Intl

4h 15m

1 stop

MDW9:45 amChicago Midway

Aug 20

MDW10:25 amChicago Midway

6h 45m

1 stop

YUL6:10 pmMontreal Pierre Elliott Trudeau Intl

$275

Porter Airlines

Aug 5

YUL10:35 amMontreal Pierre Elliott Trudeau Intl

5h 00m

1 stop

MDW2:35 pmChicago Midway

Aug 9

MDW10:20 amChicago Midway

6h 50m

1 stop

YUL6:10 pmMontreal Pierre Elliott Trudeau Intl

$276

Porter Airlines

Aug 4

YUL6:30 amMontreal Pierre Elliott Trudeau Intl

4h 15m

1 stop

MDW9:45 amChicago Midway

Aug 5

MDW3:15 pmChicago Midway

5h 55m

1 stop

YUL10:10 pmMontreal Pierre Elliott Trudeau Intl

$277

momondo Fare Finder

Use the filters below to find and compare flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 8/30

8:50 am-10:19 am

Nonstop2h 29m

Chicago O'Hare Intl

Sun 9/6

3:45 pm-9:50 pm

1 stop5h 05m

$275

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 8/10

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Thu 8/20

10:25 am-6:10 pm

1 stop6h 45m

$275

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 8/5

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Sun 8/9

10:20 am-6:10 pm

1 stop6h 50m

$276

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 8/4

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Wed 8/5

3:15 pm-10:10 pm

1 stop5h 55m

$277

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 8/22

6:30 pm-8:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 8/29

8:40 am-11:59 am

Nonstop2h 19m

$278

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/6

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Sun 8/9

10:20 am-6:10 pm

1 stop6h 50m

$278

Quickest round-trip

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 7/22

8:40 am-10:16 am

Nonstop2h 36m

Chicago O'Hare Intl

Mon 7/27

8:45 am-12:00 pm

Nonstop2h 15m

$279

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 7/29

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Wed 8/5

3:15 pm-10:10 pm

1 stop5h 55m

$279

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 7/30

12:30 pm-2:10 pm

Nonstop2h 40m

Chicago O'Hare Intl

Mon 8/3

6:30 am-10:56 pm

1 stop15h 26m

$285

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 8/6

12:47 pm-8:30 pm

1 stop8h 43m

Chicago O'Hare Intl

Sun 8/9

6:59 am-11:56 am

1 stop3h 57m

$286

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 Montreal Pierre Elliott Trudeau Intl Airport 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 Pierre Elliott Trudeau Intl Airport and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Montreal Pierre Elliott Trudeau Intl Airport, with most prices found around $60. If you’re not able to fly to Chicago in October, then May is your next best option. Flight prices from Montreal Pierre Elliott Trudeau Intl Airport to Chicago during May average around $65.

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 $424. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Montreal Pierre Elliott Trudeau Intl Airport to Chicago for around $680.

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 in the afternoon. Flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago during this time can be as low as $492. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $543.

What is the cheapest Montreal Pierre Elliott Trudeau Intl to Chicago flight route?

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

How far in advance should I book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

You are more likely to see cheaper flights to Chicago from Montreal Pierre Elliott Trudeau Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $357 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Montreal Pierre Elliott Trudeau Intl Airport for as low as $229 on momondo.

What cabin class options are available on Montreal Pierre Elliott Trudeau Intl Airport to Chicago flights?

There are 4 cabin classes available to choose from on Montreal Pierre Elliott Trudeau Intl Airport 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 Pierre Elliott Trudeau Intl Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Montreal Pierre Elliott Trudeau Intl Airport to Chicago.

How have Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight prices changed over time?

As of July 2026, prices for Montreal Pierre Elliott Trudeau Intl Airport to Chicago flights are approximately 10% more expensive when compared to flights at the same time last year.

When to book flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

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

Estimated round-trip price

Cheap Montreal Pierre Elliott Trudeau Intl Airport to Chicago (YUL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Best Price Found	$231
Fastest flight time	2h 35m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Montreal Pierre Elliott Trudeau Intl Airport in the past 72 hours is $231. The best round-trip flight deal from Montreal Pierre Elliott Trudeau Intl Airport to Chicago found on momondo in the last 72 hours is $375.

The fastest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago takes 2h 35m

Direct flights go from Montreal Pierre Elliott Trudeau Intl Airport to Chicago every day.

There are 3 airports in Chicago. From Montreal Pierre Elliott Trudeau Intl Airport there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

How far is Montreal Pierre Elliott Trudeau Intl to Chicago by plane?
The distance between Montreal Pierre Elliott Trudeau Intl and Chicago is about 734.8 mi. Flights usually cover this in 2h 35m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?
Prices for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?
There are 3 operators available for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago as of July 2026.
How old do you have to be to fly from Montreal Pierre Elliott Trudeau Intl Airport 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 Montreal Pierre Elliott Trudeau Intl Airport 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 Montreal Pierre Elliott Trudeau Intl Airport to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Montreal Pierre Elliott Trudeau Intl Airport to Chicago is Embraer 175 (Enhanced Winglets), representing 26.54% of all bookings. The subsequent popular models are Embraer 175 at 20.76%, Embraer 170 at 12.62%, and Airbus A220-300 at 8.91%.
What is the most popular airline from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?
Based on momondo bookings for flights between Montreal Pierre Elliott Trudeau Intl Airport and Chicago, the leading airline is Air Canada, making up 78% of the total bookings. Other popular airlines include Porter Airlines with 13% and United Airlines with 9%.

Best airlines flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Compare and see reviews for airlines that fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $159	Free Cancellation	Rating 7.1 11,332 reviews	Search Air Canada flights
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.1 11,809 reviews	Search American Airlines flights
United Airlines	PriceFrom $240	Free Cancellation	Rating 7.4 9,979 reviews	Search United Airlines flights

United Airlines Flights From Montreal Pierre Elliott Trudeau Intl Airport to Chicago
The lowest priced United Airlines flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from the last 72 hours was $240. Generally, United Airlines has 36 flights on this route every week with an average price of $402. United Airlines is rated 7.4/10 by our users.
Air Canada Flights From Montreal Pierre Elliott Trudeau Intl Airport to Chicago
$159 is the best Air Canada flight deal from Montreal Pierre Elliott Trudeau Intl Airport to Chicago found on momondo over the last 72 hours. The average Air Canada ticket price found was closer to $321, however, with flight time and availability significantly affecting the price. Air Canada (7.1/10 from 11,332 user reviews) flies into Chicago from Montreal Pierre Elliott Trudeau Intl Airport 41 times in an average week so prices can vary.

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Porter

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Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Montreal to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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?

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?

Yes. momondo can track prices for Montreal to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from $166

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Air Canada flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Our best Air Canada deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight tickets

Porter Airlines flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Our best Porter Airlines deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

What is the typical price of a round-trip flight between Montreal Pierre Elliott Trudeau Intl Airport and 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 Montreal Pierre Elliott Trudeau Intl to Chicago flight route?

How far in advance should I book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

What cabin class options are available on Montreal Pierre Elliott Trudeau Intl Airport to Chicago flights?

Can stopping save me money on Montreal Pierre Elliott Trudeau Intl Airport to Chicago flights?

How have Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight prices changed over time?

What is the cheapest airline that flies from Montreal Pierre Elliott Trudeau Intl to Chicago?

What airlines fly to Chicago?

How many flights depart from Montreal Pierre Elliott Trudeau Intl Airport to Chicago on average per day?

How many flights depart from Montreal Pierre Elliott Trudeau Intl Airport to Chicago on average per week?

When to book flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Cheap Montreal Pierre Elliott Trudeau Intl Airport to Chicago (YUL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Best airlines flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Compare and see reviews for airlines that fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago with momondo

United Airlines Flights From Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Air Canada Flights From Montreal Pierre Elliott Trudeau Intl Airport to Chicago

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Airports listed have a maximum distance of 78.5 mi from Chicago

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