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Cheap flights from Montreal to Chicago from C$ 148

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 27/2. 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
8:55 a.m. - 11:55 a.m.
YUL
-
MDW
4h 00m
1 stop
Porter Airlines Logo
11:05 a.m. - 5:45 p.m.
MDW
-
YUL
5h 40m
1 stop
C$ 252Porter Airlines
sáb., 14 feb. - mié., 18 feb.
United Airlines Logo
4:45 p.m. - 6:51 p.m.
YUL
-
ORD
3h 06mdirect
United Airlines Logo
1:02 p.m. - 7:48 p.m.
ORD
-
YUL
5h 46m
1 stop
C$ 253United Airlines
mié., 11 feb. - mié., 18 feb.
United Airlines Logo
9:15 a.m. - 11:39 p.m.
YUL
-
ORD
15h 24m
1 stop
United Airlines Logo
10:35 a.m. - 2:00 p.m.
ORD
-
YUL
2h 25mdirect
C$ 261United Airlines
lun., 9 feb. - dom., 15 feb.
United Airlines Logo
3:00 p.m. - 8:13 p.m.
YUL
-
ORD
6h 13m
1 stop
United Airlines Logo
1:02 p.m. - 7:48 p.m.
ORD
-
YUL
5h 46m
1 stop
C$ 275United Airlines
mié., 11 feb. - mié., 18 feb.
Porter Airlines Logo
10:15 a.m. - 3:20 p.m.
YUL
-
MDW
6h 05m
1 stop
Porter Airlines Logo
11:05 a.m. - 5:45 p.m.
MDW
-
YUL
5h 40m
1 stop
C$ 282Porter Airlines
dom., 8 feb. - lun., 9 feb.
United Airlines Logo
6:00 a.m. - 8:00 a.m.
YUL
-
ORD
3h 00mdirect
United Airlines Logo
7:10 a.m. - 1:28 p.m.
ORD
-
YUL
5h 18m
1 stop
C$ 282United Airlines
jue., 12 feb. - mar., 17 feb.
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$ 283Air Canada
vie., 8 may. - mar., 12 may.
American Airlines Logo
3:45 p.m. - 5:44 p.m.
YUL
-
ORD
2h 59mdirect
American Airlines Logo
6:40 a.m. - 10:56 p.m.
ORD
-
YUL
15h 16m
1 stop
C$ 288American Airlines
jue., 12 feb. - lun., 16 feb.
Delta Logo
12:50 p.m. - 10:22 p.m.
YUL
-
MDW
10h 32m
1 stop
Delta Logo
10:49 a.m. - 4:53 p.m.
MDW
-
YUL
5h 04m
1 stop
C$ 297Delta
mié., 11 feb. - jue., 19 feb.
Delta Logo
12:54 p.m. - 5:55 p.m.
YUL
-
MDW
6h 01m
1 stop
Delta Logo
6:00 a.m. - 4:53 p.m.
MDW
-
YUL
9h 53m
1 stop
C$ 299Delta
mié., 11 feb. - jue., 19 feb.

American Airlines flights from Montreal to Chicago

Our best American Airlines deals on Montreal to Chicago flight tickets
American Airlines
12 Feb
YUL3:45 p.m.Montreal Pierre Elliott Trudeau Intl
2h 59m
ORD5:44 p.m.Chicago O'Hare Intl
16 Feb
ORD6:40 a.m.Chicago O'Hare Intl
15h 16m
1 stop
YUL10:56 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 288
American Airlines
18 Feb
YUL7:30 a.m.Montreal Pierre Elliott Trudeau Intl
7h 27m
1 stop
ORD1:57 p.m.Chicago O'Hare Intl
23 Feb
ORD5:00 a.m.Chicago O'Hare Intl
7h 45m
1 stop
YUL1:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 303
American Airlines
12 Feb
YUL3:45 p.m.Montreal Pierre Elliott Trudeau Intl
2h 59m
ORD5:44 p.m.Chicago O'Hare Intl
15 Feb
ORD7:10 a.m.Chicago O'Hare Intl
5h 35m
1 stop
YUL1:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 359

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets
United Airlines
11 Feb
YUL4:45 p.m.Montreal Pierre Elliott Trudeau Intl
3h 06m
ORD6:51 p.m.Chicago O'Hare Intl
18 Feb
ORD1:02 p.m.Chicago O'Hare Intl
5h 46m
1 stop
YUL7:48 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 253
United Airlines
9 Feb
YUL9:15 a.m.Montreal Pierre Elliott Trudeau Intl
15h 24m
1 stop
ORD11:39 p.m.Chicago O'Hare Intl
15 Feb
ORD10:35 a.m.Chicago O'Hare Intl
2h 25m
YUL2:00 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 261
United Airlines
11 Feb
YUL9:15 a.m.Montreal Pierre Elliott Trudeau Intl
6h 10m
1 stop
ORD2:25 p.m.Chicago O'Hare Intl
19 Feb
ORD7:10 a.m.Chicago O'Hare Intl
5h 18m
1 stop
YUL1:28 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 275

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 21 enero 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

sáb. 14/2

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

1 stop4h 00m

Chicago Midway

mié. 18/2

11:05 a.m.-5:45 p.m.

1 stop5h 40m

C$ 252

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mié. 11/2

4:45 p.m.-6:51 p.m.

Nonstop3h 06m

Chicago O'Hare Intl

mié. 18/2

1:02 p.m.-7:48 p.m.

1 stop5h 46m

C$ 253

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

lun. 9/2

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

1 stop15h 24m

Chicago O'Hare Intl

dom. 15/2

10:35 a.m.-2:00 p.m.

Nonstop2h 25m

C$ 261

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mié. 11/2

3:00 p.m.-8:13 p.m.

1 stop6h 13m

Chicago O'Hare Intl

mié. 18/2

1:02 p.m.-7:48 p.m.

1 stop5h 46m

C$ 275

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

dom. 8/2

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

1 stop6h 05m

Chicago Midway

lun. 9/2

11:05 a.m.-5:45 p.m.

1 stop5h 40m

C$ 282

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

jue. 12/2

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

Nonstop3h 00m

Chicago O'Hare Intl

mar. 17/2

7:10 a.m.-1:28 p.m.

1 stop5h 18m

C$ 282

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

vie. 8/5

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

Nonstop2h 38m

Chicago O'Hare Intl

mar. 12/5

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

Nonstop2h 15m

C$ 283

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

jue. 12/2

3:45 p.m.-5:44 p.m.

Nonstop2h 59m

Chicago O'Hare Intl

lun. 16/2

6:40 a.m.-10:56 p.m.

1 stop15h 16m

C$ 288

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 11/2

12:50 p.m.-10:22 p.m.

1 stop10h 32m

Chicago Midway

jue. 19/2

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

1 stop5h 04m

C$ 297

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 11/2

12:54 p.m.-5:55 p.m.

1 stop6h 01m

Chicago Midway

jue. 19/2

6:00 a.m.-4:53 p.m.

1 stop9h 53m

C$ 299

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$ 391.

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$ 695. 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$ 1,006. 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$ 744. 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$ 1,130 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$ 490 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$ 293 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?

No. A direct flight is the cheapest option for a flight between Montreal to Chicago.

How have Montreal to Chicago flight prices changed over time?

As of January 2026, prices for Montreal to Chicago flights are approximately 32% 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$ 309

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$ 309. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is C$ 553.
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$ 178Free CancellationRating
7.2
11,173 reviews
Search American Airlines flights
Porter AirlinesPriceFrom C$ 189Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 254Free CancellationRating
7.1
10,646 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 271Free CancellationRating
7.4
9,191 reviews
Search United Airlines flights

  • Porter Airlines Flights From Montreal to Chicago

    Porter Airlines flies from Montreal to Chicago around 7 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$ 189 (round-trip), much lower than the average airfare cost of C$ 424 for Porter Airlines flights on this route.

  • United Airlines Flights From Montreal to Chicago

    United Airlines (7.4/10 from 9,191 reviews) operates around 31 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around C$ 511, with deals from around C$ 271 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