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?

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

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

As of September 2025, 206 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Fri, with 15% of weekly flights taking off on this day.

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

As of September 2025, 29 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 49% of daily flights taking off in the afternoon.

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 September 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$ 195 Cheap Flights from Montreal to Chicago in 2025

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 C$ 334 to C$ 652. The lowest price recently found on this route was C$ 324.

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Montreal to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

1:10 p.m. - 4:24 p.m.YUL-MDW

4h 14m1 stop

5:20 p.m. - 10:15 p.m.MDW-YUL

3h 55m1 stop

C$ 324Porter Airlines

Find Deal

Fri, 3 Oct - Sun, 5 Oct

10:45 a.m. - 4:24 p.m.YUL-MDW

6h 39m1 stop

9:35 a.m. - 4:00 p.m.MDW-YUL

5h 25m1 stop

C$ 325Porter Airlines

Find Deal

Fri, 17 Oct - Mon, 20 Oct

1:10 p.m. - 4:24 p.m.YUL-MDW

4h 14m1 stop

5:20 p.m. - 10:15 p.m.MDW-YUL

3h 55m1 stop

C$ 327Porter Airlines

Find Deal

Fri, 3 Oct - Sun, 5 Oct

6:15 p.m. - 8:00 p.m.YUL-ORD

2h 45mdirect

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

2h 05mdirect

C$ 334Air Canada

Find Deal

Wed, 29 Oct - Wed, 5 Nov

9:10 a.m. - 1:01 p.m.YUL-ORD

4h 51m1 stop

12:50 p.m. - 3:57 p.m.ORD-YUL

2h 07mdirect

C$ 345Air Canada

Find Deal

Wed, 29 Oct - Wed, 5 Nov

9:45 a.m. - 11:23 a.m.YUL-ORD

2h 38mdirect

7:11 a.m. - 10:40 a.m.ORD-YUL

2h 29mdirect

C$ 360United Airlines

Find Deal

Sat, 4 Oct - Tue, 7 Oct

9:45 a.m. - 11:23 a.m.YUL-ORD

2h 38mdirect

2:08 p.m. - 5:26 p.m.ORD-YUL

2h 18mdirect

C$ 363United Airlines

Find Deal

Sat, 4 Oct - Sun, 5 Oct

2:29 p.m. - 11:37 p.m.YUL-ORD

10h 08m1 stop

6:46 a.m. - 1:46 p.m.ORD-YUL

6h 00m1 stop

C$ 412American Airlines

Find Deal

Fri, 7 Nov - Tue, 11 Nov

3:52 p.m. - 5:52 p.m.YUL-ORD

3h 00mdirect

8:20 a.m. - 10:39 p.m.ORD-YUL

13h 19m1 stop

C$ 430American Airlines

Find Deal

Sun, 2 Nov - Wed, 5 Nov

2:48 p.m. - 9:10 p.m.YUL-MDW

7h 22m1 stop

12:48 p.m. - 11:31 a.m.MDW-YUL

21h 43m1 stop

C$ 443WestJet

Find Deal

Sat, 4 Oct - Wed, 8 Oct

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets

Air Canada

29 Oct

YUL6:15 p.m.Montreal Pierre Elliott Trudeau Intl

2h 45m

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

5 Nov

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

2h 05m

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

C$ 334

Find similar

Air Canada

29 Oct

YUL9:10 a.m.Montreal Pierre Elliott Trudeau Intl

4h 51m

1 stop

ORD1:01 p.m.Chicago O'Hare Intl

5 Nov

ORD12:50 p.m.Chicago O'Hare Intl

2h 07m

YUL3:57 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 345

Find similar

Air Canada

27 Oct

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

7h 20m

1 stop

ORD7:30 p.m.Chicago O'Hare Intl

3 Nov

ORD12:50 p.m.Chicago O'Hare Intl

2h 07m

YUL3:57 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 346

Find similar

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets

United Airlines

4 Oct

YUL9:45 a.m.Montreal Pierre Elliott Trudeau Intl

2h 38m

ORD11:23 a.m.Chicago O'Hare Intl

7 Oct

ORD7:11 a.m.Chicago O'Hare Intl

2h 29m

YUL10:40 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 360

Find similar

United Airlines

4 Oct

YUL9:45 a.m.Montreal Pierre Elliott Trudeau Intl

2h 38m

ORD11:23 a.m.Chicago O'Hare Intl

5 Oct

ORD2:08 p.m.Chicago O'Hare Intl

2h 18m

YUL5:26 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 363

Find similar

United Airlines

3 Oct

YUL9:45 a.m.Montreal Pierre Elliott Trudeau Intl

2h 38m

ORD11:23 a.m.Chicago O'Hare Intl

5 Oct

ORD7:11 a.m.Chicago O'Hare Intl

2h 29m

YUL10:40 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 367

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Sun 5/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 324

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Mon 20/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 325

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Sun 5/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 327

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 29/10

6:15 p.m.-8:00 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Wed 5/11

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

Nonstop2h 05m

C$ 334

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 29/10

9:10 a.m.-1:01 p.m.

1 stop4h 51m

Chicago O'Hare Intl

Wed 5/11

12:50 p.m.-3:57 p.m.

Nonstop2h 07m

C$ 345

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/10

9:45 a.m.-11:23 a.m.

Nonstop2h 38m

Chicago O'Hare Intl

Tue 7/10

7:11 a.m.-10:40 a.m.

Nonstop2h 29m

C$ 360

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/10

9:45 a.m.-11:23 a.m.

Nonstop2h 38m

Chicago O'Hare Intl

Sun 5/10

2:08 p.m.-5:26 p.m.

Nonstop2h 18m

C$ 363

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 7/11

2:29 p.m.-11:37 p.m.

1 stop10h 08m

Chicago O'Hare Intl

Tue 11/11

6:46 a.m.-1:46 p.m.

1 stop6h 00m

C$ 412

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 2/11

3:52 p.m.-5:52 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Wed 5/11

8:20 a.m.-10:39 p.m.

1 stop13h 19m

C$ 430

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 4/10

2:48 p.m.-9:10 p.m.

1 stop7h 22m

Chicago Midway

Wed 8/10

12:48 p.m.-11:31 a.m.

1 stop21h 43m

C$ 443

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 typical price of a round-trip flight between Montreal and Chicago?

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Montreal averaging around C$ 417.

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 C$ 756. 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$ 1,000. 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$ 775. 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$ 1,044 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$ 529 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$ 291 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 12% 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 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	C$ 460
Fastest flight time	2h 28m
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$ 460. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is C$ 517.

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

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 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 were last updated today.
How many operators does momondo search for flights from Montreal to Chicago?
As of September 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 26.24% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 16.25%, Embraer 175 at 15.57%, and Airbus A321-100/200 at 10.85%.
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 58% of the total bookings. Other popular airlines include Porter Airlines with 32%, 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$ 178	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Porter Airlines	PriceFrom C$ 197	Free Cancellation	Rating 7.9 363 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 261	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 357	Free Cancellation	Rating 7.4 8,931 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 453	Free Cancellation	Rating 7.2 3,091 reviews	Search WestJet flights

United Airlines Flights From Montreal to Chicago
United Airlines flies from Montreal to Chicago around 41 times per week, with 8,931 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Montreal to Chicago in the last 72 hours was C$ 258 (round-trip), much lower than the average airfare cost of C$ 354 for United Airlines flights on this route.
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 C$ 299, 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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Tue 14/10

Tue 21/10

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Cheap flights from Montreal to Chicago from C$ 195

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 2/11. 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

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

momondo Fare Finder

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 June is another great option to travel to Chicago, with average flight prices from Montreal averaging around C$ 417.

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 12% 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 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 United Airlines 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 September 2025, 29 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 49% of daily flights taking off in the afternoon.

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

As of September 2025, 206 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Fri, 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

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