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

As of October 2025, 184 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.

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

As of October 2025, 26 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 52% of daily flights taking off at noon.

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 69% of people opting to fly with this airline when travelling 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?

American Airlines, Delta, and Air Canada 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 were last updated today.

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

As of October 2025, there are 5 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$ 189 Cheap Flights from Montreal to Chicago in 2025/26

1 adult

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One-way

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Cheap round-trip flights

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6:00 a.m. - 12:35 p.m.YUL-MDW

7h 35m1 stop

6:00 a.m. - 5:04 p.m.MDW-YUL

10h 04m1 stop

C$ 298Delta

Find Deal

Thu, 22 Jan - Sun, 25 Jan

11:10 a.m. - 3:10 p.m.YUL-ORD

5h 00m1 stop

7:15 a.m. - 10:20 a.m.ORD-YUL

2h 05mdirect

C$ 317Air Canada

Find Deal

Fri, 9 Jan - Sun, 11 Jan

6:45 a.m. - 10:05 a.m.YUL-MDW

4h 20m1 stop

4:15 p.m. - 10:45 p.m.MDW-YUL

5h 30m1 stop

C$ 324Porter Airlines

Find Deal

Thu, 15 Jan - Sun, 18 Jan

6:45 a.m. - 10:05 a.m.YUL-MDW

4h 20m1 stop

11:00 a.m. - 5:45 p.m.MDW-YUL

5h 45m1 stop

C$ 335Porter Airlines

Find Deal

Fri, 9 Jan - Sun, 11 Jan

6:00 a.m. - 8:00 a.m.YUL-ORD

3h 00mdirect

5:55 p.m. - 9:17 p.m.ORD-YUL

2h 22mdirect

C$ 363United Airlines

Find Deal

Thu, 6 Nov - Sat, 8 Nov

6:00 a.m. - 8:00 a.m.YUL-ORD

3h 00mdirect

7:15 a.m. - 1:28 p.m.ORD-YUL

5h 13m1 stop

C$ 376United Airlines

Find Deal

Thu, 6 Nov - Tue, 11 Nov

12:59 p.m. - 5:44 p.m.YUL-ORD

5h 45m1 stop

11:48 a.m. - 3:09 p.m.ORD-YUL

2h 21mdirect

C$ 409American Airlines

Find Deal

Mon, 10 Nov - Mon, 17 Nov

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

3h 00mdirect

11:49 a.m. - 3:10 p.m.ORD-YUL

2h 21mdirect

C$ 423American Airlines

Find Deal

Fri, 12 Dec - Sun, 14 Dec

7:00 a.m. - 1:08 p.m.YUL-MDW

7h 08m1 stop

10:47 a.m. - 5:21 p.m.MDW-YUL

5h 34m1 stop

C$ 468WestJet

Find Deal

Sat, 8 Nov - Thu, 13 Nov

7:10 a.m. - 6:18 p.m.YUL-MDW

12h 08m1 stop

11:48 a.m. - 1:49 p.m.MDW-YUL

25h 01m1 stop

C$ 469WestJet

Find Deal

Wed, 17 Dec - Sun, 21 Dec

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets

United Airlines

6 Nov

YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl

3h 00m

ORD8:00 a.m.Chicago O'Hare Intl

8 Nov

ORD5:55 p.m.Chicago O'Hare Intl

2h 22m

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

C$ 363

Find similar

United Airlines

6 Nov

YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl

3h 00m

ORD8:00 a.m.Chicago O'Hare Intl

11 Nov

ORD7:15 a.m.Chicago O'Hare Intl

5h 13m

1 stop

YUL1:28 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 376

Find similar

United Airlines

4 Nov

YUL3:00 p.m.Montreal Pierre Elliott Trudeau Intl

7h 16m

1 stop

ORD9:16 p.m.Chicago O'Hare Intl

9 Nov

ORD5:55 p.m.Chicago O'Hare Intl

2h 22m

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

C$ 384

Find similar

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets

Air Canada

9 Jan

YUL11:10 a.m.Montreal Pierre Elliott Trudeau Intl

5h 00m

1 stop

ORD3:10 p.m.Chicago O'Hare Intl

11 Jan

ORD7:15 a.m.Chicago O'Hare Intl

2h 05m

YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 317

Find similar

Air Canada

15 Dec

YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl

2h 45m

ORD2:55 p.m.Chicago O'Hare Intl

6 Jan

ORD7:15 a.m.Chicago O'Hare Intl

2h 05m

YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 328

Find similar

Air Canada

6 Jan

YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl

3h 05m

ORD8:05 a.m.Chicago O'Hare Intl

7 Jan

ORD7:15 a.m.Chicago O'Hare Intl

2h 05m

YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 335

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/1

6:00 a.m.-12:35 p.m.

1 stop7h 35m

Chicago Midway

Sun 25/1

6:00 a.m.-5:04 p.m.

1 stop10h 04m

C$ 298

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 9/1

11:10 a.m.-3:10 p.m.

1 stop5h 00m

Chicago O'Hare Intl

Sun 11/1

7:15 a.m.-10:20 a.m.

Nonstop2h 05m

C$ 317

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 15/1

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 18/1

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 324

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 9/1

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 11/1

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 335

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 6/11

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

Sat 8/11

5:55 p.m.-9:17 p.m.

Nonstop2h 22m

C$ 363

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 6/11

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

Tue 11/11

7:15 a.m.-1:28 p.m.

1 stop5h 13m

C$ 376

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 10/11

12:59 p.m.-5:44 p.m.

1 stop5h 45m

Chicago O'Hare Intl

Mon 17/11

11:48 a.m.-3:09 p.m.

Nonstop2h 21m

C$ 409

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 12/12

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

Nonstop3h 00m

Chicago O'Hare Intl

Sun 14/12

11:49 a.m.-3:10 p.m.

Nonstop2h 21m

C$ 423

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 8/11

7:00 a.m.-1:08 p.m.

1 stop7h 08m

Chicago Midway

Thu 13/11

10:47 a.m.-5:21 p.m.

1 stop5h 34m

C$ 468

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 17/12

7:10 a.m.-6:18 p.m.

1 stop12h 08m

Chicago Midway

Sun 21/12

11:48 a.m.-1:49 p.m.

1 stop25h 01m

C$ 469

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 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 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$ 404.

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$ 749. 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 Monday because tickets tend to average around C$ 1,003. 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$ 771. 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$ 1,008 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$ 536 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$ 324 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 14% 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 October 2025, prices for Montreal to Chicago flights are approximately 34% 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$ 321
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$ 321. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is C$ 583.

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 45m 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 October 2025, there are 5 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 28.85% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 15.48%, Embraer 175 at 12.71%, and Airbus A321-100/200 at 11.01%.
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 59% of the total bookings. Other popular airlines include Porter Airlines with 31%, United Airlines with 5%, 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
American Airlines	PriceFrom C$ 180	Free Cancellation	Rating 7.2 11,044 reviews	Search American Airlines flights
Porter Airlines	PriceFrom C$ 199	Free Cancellation	Rating 8.0 379 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 262	Free Cancellation	Rating 7.1 10,298 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 365	Free Cancellation	Rating 7.4 8,977 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 459	Free Cancellation	Rating 7.2 3,125 reviews	Search WestJet flights

United Airlines Flights From Montreal to Chicago
United Airlines flies from Montreal to Chicago around 35 times per week, with 8,977 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Montreal to Chicago in the last 72 hours was C$ 260 (round-trip), much lower than the average airfare cost of C$ 359 for United Airlines flights on this route.
American Airlines Flights From Montreal to Chicago
American Airlines (7.2/10 from 11,044 reviews) operates around 1 flight from Montreal to Chicago in any given week. The average American Airlines airfare for this route is around C$ 327, with deals from around C$ 128 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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Thu 13/11

Thu 20/11

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Cheap flights from Montreal to Chicago from C$ 189

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.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Montreal to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets

Air Canada flights from Montreal to Chicago

Our best Air Canada 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 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$ 404.

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 14% 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 October 2025, prices for Montreal to Chicago flights are approximately 34% cheaper when compared to flights at the same time last year.

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

American Airlines, Delta, and Air Canada 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 October 2025, 26 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 52% of daily flights taking off at noon.

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

As of October 2025, 184 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

United Airlines Flights From Montreal to Chicago

American 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