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Cheap flights from Montreal to Chicago from C$ 137

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 16/3. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 236Porter Airlines
Fri, 10 Apr - Sun, 12 Apr
Air Canada Logo
6:30 p.m. - 8:08 p.m.
YUL
-
ORD
2h 38mdirect
Air Canada Logo
8:45 a.m. - 12:00 p.m.
ORD
-
YUL
2h 15mdirect
C$ 239Air Canada
Fri, 1 May - Mon, 4 May
Air Canada Logo
6:25 p.m. - 8:10 p.m.
YUL
-
ORD
2h 45mdirect
Air Canada Logo
12:50 p.m. - 4:05 p.m.
ORD
-
YUL
2h 15mdirect
C$ 241Air Canada
Wed, 25 Mar - Mon, 30 Mar
Porter Airlines Logo
8:55 a.m. - 11:50 a.m.
YUL
-
MDW
3h 55m
1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m
1 stop
C$ 241Porter Airlines
Sat, 25 Apr - Wed, 29 Apr
Porter Airlines Logo
10:15 a.m. - 3:20 p.m.
YUL
-
MDW
6h 05m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:15 p.m.
MDW
-
YUL
6h 50m
1 stop
C$ 246Porter Airlines
Wed, 29 Apr - Wed, 6 May
Air Canada Logo
1:10 p.m. - 2:55 p.m.
YUL
-
ORD
2h 45mdirect
Air Canada Logo
7:15 a.m. - 10:20 a.m.
ORD
-
YUL
2h 05mdirect
C$ 249Air Canada
Sun, 8 Mar - Sun, 15 Mar
United Airlines Logo
9:45 a.m. - 11:28 a.m.
YUL
-
ORD
2h 43mdirect
United Airlines Logo
4:25 p.m. - 12:13 a.m.
ORD
-
YUL
6h 48m
1 stop
C$ 253United Airlines
Fri, 1 May - Mon, 4 May
United Airlines Logo
6:00 a.m. - 8:00 a.m.
YUL
-
ORD
3h 00mdirect
United Airlines Logo
4:20 p.m. - 12:13 a.m.
ORD
-
YUL
6h 53m
1 stop
C$ 254United Airlines
Thu, 26 Mar - Mon, 30 Mar
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 256Porter Airlines
Fri, 10 Apr - Sun, 12 Apr
American Airlines Logo
3:45 p.m. - 5:45 p.m.
YUL
-
ORD
3h 00mdirect
American Airlines Logo
6:44 p.m. - 1:45 p.m.
ORD
-
YUL
18h 01m
1 stop
C$ 262American Airlines
Thu, 12 Mar - Mon, 16 Mar

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets
United Airlines
1 May
YUL9:45 a.m.Montreal Pierre Elliott Trudeau Intl
2h 43m
ORD11:28 a.m.Chicago O'Hare Intl
4 May
ORD4:25 p.m.Chicago O'Hare Intl
6h 48m
1 stop
YUL12:13 a.m.Montreal Pierre Elliott Trudeau Intl
C$ 253
United Airlines
26 Mar
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
3h 00m
ORD8:00 a.m.Chicago O'Hare Intl
30 Mar
ORD4:20 p.m.Chicago O'Hare Intl
6h 53m
1 stop
YUL12:13 a.m.Montreal Pierre Elliott Trudeau Intl
C$ 254
United Airlines
4 May
YUL6:35 p.m.Montreal Pierre Elliott Trudeau Intl
6h 09m
1 stop
ORD11:44 p.m.Chicago O'Hare Intl
9 May
ORD6:03 p.m.Chicago O'Hare Intl
2h 23m
YUL9:26 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 261

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets
Air Canada
1 May
YUL6:30 p.m.Montreal Pierre Elliott Trudeau Intl
2h 38m
ORD8:08 p.m.Chicago O'Hare Intl
4 May
ORD8:45 a.m.Chicago O'Hare Intl
2h 15m
YUL12:00 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 239
Air Canada
25 Mar
YUL6:25 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 p.m.Chicago O'Hare Intl
30 Mar
ORD12:50 p.m.Chicago O'Hare Intl
2h 15m
YUL4:05 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 241
Air Canada
8 Mar
YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl
2h 45m
ORD2:55 p.m.Chicago O'Hare Intl
15 Mar
ORD7:15 a.m.Chicago O'Hare Intl
2h 05m
YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl
C$ 249

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 8 February 2026.
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 - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/4

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

1 stop4h 20m

Chicago Midway

Sun 12/4

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 236

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 1/5

6:30 p.m.-8:08 p.m.

Nonstop2h 38m

Chicago O'Hare Intl

Mon 4/5

8:45 a.m.-12:00 p.m.

Nonstop2h 15m

C$ 239

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 25/3

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

Nonstop2h 45m

Chicago O'Hare Intl

Mon 30/3

12:50 p.m.-4:05 p.m.

Nonstop2h 15m

C$ 241

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 25/4

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Wed 29/4

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

1 stop4h 30m

C$ 241

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 29/4

10:15 a.m.-3:20 p.m.

1 stop6h 05m

Chicago Midway

Wed 6/5

10:25 a.m.-6:15 p.m.

1 stop6h 50m

C$ 246

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 8/3

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

Nonstop2h 45m

Chicago O'Hare Intl

Sun 15/3

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

Nonstop2h 05m

C$ 249

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 1/5

9:45 a.m.-11:28 a.m.

Nonstop2h 43m

Chicago O'Hare Intl

Mon 4/5

4:25 p.m.-12:13 a.m.

1 stop6h 48m

C$ 253

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 26/3

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

Nonstop3h 00m

Chicago O'Hare Intl

Mon 30/3

4:20 p.m.-12:13 a.m.

1 stop6h 53m

C$ 254

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/4

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

1 stop4h 20m

Chicago Midway

Sun 12/4

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 256

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 12/3

3:45 p.m.-5:45 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Mon 16/3

6:44 p.m.-1:45 p.m.

1 stop18h 01m

C$ 262

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$ 387.

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$ 694. 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 Sunday because tickets tend to average around C$ 1,028. 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$ 763. 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$ 1,153 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$ 481 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$ 290 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 15% 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 February 2026, prices for Montreal to Chicago flights are approximately 34% 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$ 305

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$ 305. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is C$ 530.
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
American AirlinesPriceFrom C$ 176Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights
Porter AirlinesPriceFrom C$ 187Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 251Free CancellationRating
7.1
10,697 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 262Free CancellationRating
7.4
9,254 reviews
Search United Airlines flights

  • Porter Airlines Flights From Montreal to Chicago

    Porter Airlines flies from Montreal to Chicago around 6 times per week, with 412 momondo users rating the airline 7.9/10. The cheapest Porter Airlines deal from Montreal to Chicago in the last 72 hours was C$ 187 (round-trip), much lower than the average airfare cost of C$ 440 for Porter Airlines flights on this route.

  • United Airlines Flights From Montreal to Chicago

    United Airlines (7.4/10 from 9,254 reviews) operates around 33 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around C$ 499, with deals from around C$ 262 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.

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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