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Cheap flights from Montreal to Chicago from C$ 234

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 20/1. 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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Find the cheapest flights from Montreal to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
1:10 p.m. - 2:55 p.m.
YUL
-
ORD
2h 45mdirect
Air Canada Logo
12:50 p.m. - 4:01 p.m.
ORD
-
YUL
2h 11mdirect
C$ 253Air Canada
Sat, 7 Feb - Sat, 14 Feb
Air Canada Logo
6:25 p.m. - 8:10 p.m.
YUL
-
ORD
2h 45mdirect
Air Canada Logo
12:50 p.m. - 4:01 p.m.
ORD
-
YUL
2h 11mdirect
C$ 255Air Canada
Sat, 7 Feb - Sat, 14 Feb
Air Canada Logo
9:25 a.m. - 11:06 a.m.
YUL
-
ORD
2h 41mdirect
Air Canada Logo
12:50 p.m. - 4:01 p.m.
ORD
-
YUL
2h 11mdirect
C$ 256Air Canada
Sat, 7 Feb - Sat, 14 Feb
Air Canada Logo
9:25 a.m. - 11:06 a.m.
YUL
-
ORD
2h 41mdirect
Air Canada Logo
12:50 p.m. - 4:01 p.m.
ORD
-
YUL
2h 11mdirect
C$ 259Air Canada
Sat, 7 Feb - Sat, 14 Feb
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.
MDW
-
YUL
5h 30m1 stop
C$ 263Porter Airlines
Sun, 15 Feb - Sun, 15 Feb
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m1 stop
C$ 270Porter Airlines
Thu, 19 Feb - Mon, 23 Feb
American Airlines Logo
3:55 p.m. - 5:55 p.m.
YUL
-
ORD
3h 00mdirect
American Airlines Logo
11:46 a.m. - 3:05 p.m.
ORD
-
YUL
2h 19mdirect
C$ 270American Airlines
Fri, 13 Feb - Mon, 16 Feb
American Airlines Logo
3:50 p.m. - 5:50 p.m.
YUL
-
ORD
3h 00mdirect
American Airlines Logo
6:33 a.m. - 12:23 p.m.
ORD
-
YUL
4h 50m1 stop
C$ 271American Airlines
Sat, 7 Feb - Sat, 14 Feb
Delta Logo
6:00 a.m. - 12:46 p.m.
YUL
-
MDW
7h 46m1 stop
Delta Logo
10:49 a.m. - 4:53 p.m.
MDW
-
YUL
5h 04m1 stop
C$ 296Delta
Sat, 14 Feb - Wed, 18 Feb
Delta Logo
7:00 a.m. - 11:59 a.m.
YUL
-
MDW
5h 59m1 stop
Delta Logo
9:34 a.m. - 3:55 p.m.
MDW
-
YUL
5h 21m1 stop
C$ 297Delta
Tue, 17 Feb - Thu, 19 Feb

American Airlines flights from Montreal to Chicago

Our best American Airlines deals on Montreal to Chicago flight tickets
American Airlines
7 Feb
YUL3:50 p.m.Montreal Pierre Elliott Trudeau Intl
3h 00m
ORD5:50 p.m.Chicago O'Hare Intl
14 Feb
ORD6:33 a.m.Chicago O'Hare Intl
4h 50m
1 stop
YUL12:23 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 271
Find similar
American Airlines
7 Feb
YUL3:50 p.m.Montreal Pierre Elliott Trudeau Intl
3h 00m
ORD5:50 p.m.Chicago O'Hare Intl
14 Feb
ORD6:33 a.m.Chicago O'Hare Intl
4h 50m
1 stop
YUL12:23 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 275
Find similar
American Airlines
13 Feb
YUL3:55 p.m.Montreal Pierre Elliott Trudeau Intl
3h 00m
ORD5:55 p.m.Chicago O'Hare Intl
16 Feb
ORD1:53 p.m.Chicago O'Hare Intl
7h 51m
1 stop
YUL10:44 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 277
Find similar

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets
Air Canada
7 Feb
YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD2:55 p.m.Chicago O'Hare Intl
14 Feb
ORD12:50 p.m.Chicago O'Hare Intl
2h 11m
YUL4:01 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 253
Find similar
Air Canada
7 Feb
YUL6:25 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 p.m.Chicago O'Hare Intl
14 Feb
ORD12:50 p.m.Chicago O'Hare Intl
2h 11m
YUL4:01 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 255
Find similar
Air Canada
7 Feb
YUL9:25 a.m.Montreal Pierre Elliott Trudeau Intl
2h 41m
ORD11:06 a.m.Chicago O'Hare Intl
14 Feb
ORD12:50 p.m.Chicago O'Hare Intl
2h 11m
YUL4:01 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 256
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montreal to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 23 December 2025.
Use the filters below to find and compare flights from Montreal to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 7/2

1:10 p.m.-2:55 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Sat 14/2

12:50 p.m.-4:01 p.m.

Nonstop2h 11m

C$ 253

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 7/2

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

Nonstop2h 45m

Chicago O'Hare Intl

Sat 14/2

12:50 p.m.-4:01 p.m.

Nonstop2h 11m

C$ 255

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 7/2

9:25 a.m.-11:06 a.m.

Nonstop2h 41m

Chicago O'Hare Intl

Sat 14/2

12:50 p.m.-4:01 p.m.

Nonstop2h 11m

C$ 256

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 7/2

9:25 a.m.-11:06 a.m.

Nonstop2h 41m

Chicago O'Hare Intl

Sat 14/2

12:50 p.m.-4:01 p.m.

Nonstop2h 11m

C$ 259

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/2

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

1 stop4h 20m

Chicago Midway

Sun 15/2

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

1 stop5h 30m

C$ 263

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/2

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

1 stop4h 20m

Chicago Midway

Mon 23/2

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 270

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 13/2

3:55 p.m.-5:55 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Mon 16/2

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

Nonstop2h 19m

C$ 270

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 7/2

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

Nonstop3h 00m

Chicago O'Hare Intl

Sat 14/2

6:33 a.m.-12:23 p.m.

1 stop4h 50m

C$ 271

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 14/2

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Wed 18/2

10:49 a.m.-4:53 p.m.

1 stop5h 04m

C$ 296

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 17/2

7:00 a.m.-11:59 a.m.

1 stop5h 59m

Chicago Midway

Thu 19/2

9:34 a.m.-3:55 p.m.

1 stop5h 21m

C$ 297

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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$ 390.

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$ 705. 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$ 952. 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$ 733. 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$ 1,091 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$ 487 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$ 318 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 19% 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 12% 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$ 283

Fastest flight time

2h 35m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Montreal in the past 72 hours is C$ 283. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is C$ 640.
The fastest flight from Montreal to Chicago takes 2h 35m
Direct flights go from Montreal to Chicago every day.
There are 3 airports in Chicago. From Montreal there are direct flights to 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 35m 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 196Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights
American AirlinesPriceFrom C$ 202Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
Air CanadaPriceFrom C$ 256Free CancellationRating
7.1
10,551 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 264Free CancellationRating
7.4
9,106 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 399 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Montreal to Chicago in the last 72 hours was C$ 196 (round-trip), much lower than the average airfare cost of C$ 519 for Porter Airlines flights on this route.

  • United Airlines Flights From Montreal to Chicago

    United Airlines (7.4/10 from 9,106 reviews) operates around 35 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around C$ 494, with deals from around C$ 264 rare but found on momondo. Referenced prices are for round-trip Montreal to Chicago flight searches in the last 72 hours.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport