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

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

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

As of December 2025, 134 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

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 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?

As of December 2025, 19 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 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 December 2025, there are 4 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$ 227 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 C$ 431 to C$ 599. The lowest price recently found on this route was C$ 270.

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

Enter your travel dates to find the best prices.

9:15 a.m. - 11:39 p.m.YUL-ORD

15h 24m1 stop

6:00 p.m. - 9:17 p.m.ORD-YUL

2h 17mdirect

C$ 270United Airlines

Find Deal

Sun, 1 Feb - Sat, 28 Feb

11:25 a.m. - 3:20 p.m.YUL-MDW

4h 55m1 stop

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

5h 30m1 stop

C$ 278Porter Airlines

Find Deal

Wed, 18 Mar - Mon, 23 Mar

12:58 p.m. - 6:01 p.m.YUL-ORD

6h 03m1 stop

11:46 a.m. - 3:05 p.m.ORD-YUL

2h 19mdirect

C$ 283American Airlines

Find Deal

Wed, 18 Feb - Sun, 22 Feb

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$ 284Porter Airlines

Find Deal

Wed, 18 Feb - Sun, 22 Feb

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

6h 00m1 stop

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

2h 05mdirect

C$ 285Air Canada

Find Deal

Thu, 5 Feb - Sun, 15 Feb

6:25 p.m. - 8:10 p.m.YUL-ORD

2h 45mdirect

2:00 p.m. - 8:49 p.m.ORD-YUL

5h 49m2 stops

C$ 288Air Canada

Find Deal

Thu, 15 Jan - Thu, 22 Jan

6:25 p.m. - 8:10 p.m.YUL-ORD

2h 45mdirect

8:00 a.m. - 2:22 p.m.ORD-YUL

5h 22m1 stop

C$ 290Air Canada

Find Deal

Thu, 15 Jan - Thu, 22 Jan

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

5h 00m1 stop

2:00 p.m. - 8:49 p.m.ORD-YUL

5h 49m2 stops

C$ 291Air Canada

Find Deal

Thu, 15 Jan - Thu, 22 Jan

6:00 a.m. - 12:48 p.m.YUL-MDW

7h 48m1 stop

6:35 p.m. - 11:12 p.m.MDW-YUL

3h 37m1 stop

C$ 311Delta

Find Deal

Thu, 15 Jan - Mon, 19 Jan

6:00 a.m. - 12:48 p.m.YUL-MDW

7h 48m1 stop

6:00 a.m. - 4:55 p.m.MDW-YUL

9h 55m1 stop

C$ 326Delta

Find Deal

Thu, 15 Jan - Thu, 22 Jan

Delta flights from Montreal to Chicago

Our best Delta deals on Montreal to Chicago flight tickets

Delta

8 Jan

YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl

10h 44m

1 stop

ORD4:44 p.m.Chicago O'Hare Intl

10 Jan

ORD6:15 a.m.Chicago O'Hare Intl

6h 27m

1 stop

YUL1:42 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 311

Find similar

Delta

15 Jan

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

7h 48m

1 stop

MDW12:48 p.m.Chicago Midway

22 Jan

MDW6:00 a.m.Chicago Midway

9h 55m

1 stop

YUL4:55 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 326

Find similar

Delta

12 Feb

YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl

5h 59m

1 stop

MDW11:59 a.m.Chicago Midway

16 Feb

MDW1:26 p.m.Chicago Midway

9h 00m

1 stop

YUL11:26 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 358

Find similar

American Airlines flights from Montreal to Chicago

Our best American Airlines deals on Montreal to Chicago flight tickets

American Airlines

18 Feb

YUL12:58 p.m.Montreal Pierre Elliott Trudeau Intl

6h 03m

1 stop

ORD6:01 p.m.Chicago O'Hare Intl

22 Feb

ORD11:46 a.m.Chicago O'Hare Intl

2h 19m

YUL3:05 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 283

Find similar

American Airlines

15 Jan

YUL3:50 p.m.Montreal Pierre Elliott Trudeau Intl

3h 00m

ORD5:50 p.m.Chicago O'Hare Intl

18 Jan

ORD11:50 a.m.Chicago O'Hare Intl

2h 18m

YUL3:08 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 302

Find similar

American Airlines

15 Jan

YUL3:50 p.m.Montreal Pierre Elliott Trudeau Intl

3h 00m

ORD5:50 p.m.Chicago O'Hare Intl

18 Jan

ORD6:42 a.m.Chicago O'Hare Intl

7h 38m

1 stop

YUL3:20 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 309

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 1/2

9:15 a.m.-11:39 p.m.

1 stop15h 24m

Chicago O'Hare Intl

Sat 28/2

6:00 p.m.-9:17 p.m.

Nonstop2h 17m

C$ 270

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/3

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Mon 23/3

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

1 stop5h 30m

C$ 278

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 18/2

12:58 p.m.-6:01 p.m.

1 stop6h 03m

Chicago O'Hare Intl

Sun 22/2

11:46 a.m.-3:05 p.m.

Nonstop2h 19m

C$ 283

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/2

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

1 stop4h 20m

Chicago Midway

Sun 22/2

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

1 stop5h 30m

C$ 284

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 5/2

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

1 stop6h 00m

Chicago O'Hare Intl

Sun 15/2

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

Nonstop2h 05m

C$ 285

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 15/1

6:25 p.m.-8:10 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Thu 22/1

2:00 p.m.-8:49 p.m.

2 stops5h 49m

C$ 288

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 15/1

6:25 p.m.-8:10 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Thu 22/1

8:00 a.m.-2:22 p.m.

1 stop5h 22m

C$ 290

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 15/1

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

1 stop5h 00m

Chicago O'Hare Intl

Thu 22/1

2:00 p.m.-8:49 p.m.

2 stops5h 49m

C$ 291

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 15/1

6:00 a.m.-12:48 p.m.

1 stop7h 48m

Chicago Midway

Mon 19/1

6:35 p.m.-11:12 p.m.

1 stop3h 37m

C$ 311

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 15/1

6:00 a.m.-12:48 p.m.

1 stop7h 48m

Chicago Midway

Thu 22/1

6:00 a.m.-4:55 p.m.

1 stop9h 55m

C$ 326

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 March is another great option to travel to Chicago, with average flight prices from Montreal averaging around C$ 397.

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$ 729. 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$ 986. 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$ 743. 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$ 1,065 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$ 514 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$ 323 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 26% 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 December 2025, prices for Montreal to Chicago flights are approximately 11% more expensive 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$ 375
Fastest flight time	2h 34m
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$ 375. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is C$ 580.

The fastest flight from Montreal to Chicago takes 2h 34m

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 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 were last updated today.
How many operators does momondo search for flights from Montreal to Chicago?
As of December 2025, there are 4 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 31.68% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet 900 at 15.52%, Embraer 170 at 10.50%, and Embraer 175 at 8.15%.
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 64% of the total bookings. Other popular airlines include Porter Airlines with 29%, United Airlines with 6%, and American Airlines with 2%.

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
Porter Airlines	PriceFrom C$ 199	Free Cancellation	Rating 8.0 394 reviews	Search Porter Airlines flights
American Airlines	PriceFrom C$ 206	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Air Canada	PriceFrom C$ 261	Free Cancellation	Rating 7.1 10,496 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 268	Free Cancellation	Rating 7.4 9,063 reviews	Search United Airlines flights

Porter Airlines Flights From Montreal to Chicago
Porter Airlines flies from Montreal to Chicago around 2 times per week, with 394 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Montreal to Chicago in the last 72 hours was C$ 199 (round-trip), much lower than the average airfare cost of C$ 454 for Porter Airlines flights on this route.
United Airlines Flights From Montreal to Chicago
United Airlines (7.4/10 from 9,063 reviews) operates around 34 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around C$ 508, with deals from around C$ 268 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

Fri 2/1

Fri 9/1

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$ 227

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 24/12. 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

Delta flights from Montreal to Chicago

Our best Delta deals on Montreal to Chicago flight tickets

American Airlines flights from Montreal to Chicago

Our best American 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 March is another great option to travel to Chicago, with average flight prices from Montreal averaging around C$ 397.

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 26% 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 December 2025, prices for Montreal to Chicago flights are approximately 11% more expensive when compared to flights at the same time last year.

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

Porter Airlines, American Airlines, 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 December 2025, 19 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 in the afternoon.

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

As of December 2025, 134 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Mon, 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

Porter Airlines Flights From Montreal to Chicago

United 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