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Cheap flights from Montreal to Chicago from $164

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 12/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:45 am - 10:05 am
YUL
-
MDW
4h 20m1 stop
Porter Airlines Logo
12:45 pm - 6:45 pm
MDW
-
YUL
5h 00m1 stop
$188Porter Airlines
Thu, Feb 12 - Sat, Feb 14
United Airlines Logo
6:00 am - 8:00 am
YUL
-
ORD
3h 00mnonstop
United Airlines Logo
6:00 pm - 9:17 pm
ORD
-
YUL
2h 17mnonstop
$189United Airlines
Thu, Feb 12 - Sat, Feb 14
Porter Airlines Logo
11:25 am - 3:20 pm
YUL
-
MDW
4h 55m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pm
MDW
-
YUL
5h 30m1 stop
$189Porter Airlines
Fri, Feb 13 - Mon, Feb 16
United Airlines Logo
6:00 am - 8:05 am
YUL
-
ORD
3h 05mnonstop
United Airlines Logo
5:52 pm - 9:17 pm
ORD
-
YUL
2h 25mnonstop
$190United Airlines
Thu, Feb 5 - Sun, Feb 8
American Airlines Logo
3:50 pm - 5:50 pm
YUL
-
ORD
3h 00mnonstop
American Airlines Logo
11:50 am - 3:08 pm
ORD
-
YUL
2h 18mnonstop
$193American Airlines
Fri, Feb 6 - Mon, Feb 9
American Airlines Logo
3:50 pm - 5:50 pm
YUL
-
ORD
3h 00mnonstop
American Airlines Logo
11:50 am - 3:08 pm
ORD
-
YUL
2h 18mnonstop
$194American Airlines
Fri, Feb 6 - Mon, Feb 9
United Airlines Logo
9:15 am - 2:25 pm
YUL
-
ORD
6h 10m1 stop
United Airlines Logo
10:35 am - 2:00 pm
ORD
-
YUL
2h 25mnonstop
$195United Airlines
Mon, Feb 9 - Wed, Feb 18
United Airlines Logo
4:45 pm - 6:51 pm
YUL
-
ORD
3h 06mnonstop
United Airlines Logo
1:00 pm - 7:48 pm
ORD
-
YUL
5h 48m1 stop
$196United Airlines
Fri, Feb 6 - Mon, Feb 9
Porter Airlines Logo
6:45 am - 10:05 am
YUL
-
MDW
4h 20m1 stop
Porter Airlines Logo
11:00 am - 4:30 pm
MDW
-
YUL
4h 30m1 stop
$196Porter Airlines
Sun, Feb 15 - Tue, Feb 17
Delta Logo
12:50 pm - 10:22 pm
YUL
-
MDW
10h 32m1 stop
Delta Logo
1:26 pm - 11:12 pm
MDW
-
YUL
8h 46m1 stop
$216Delta
Thu, Feb 5 - Sat, Feb 7

United Airlines flights from Montreal to Chicago

Our best United Airlines deals on Montreal to Chicago flight tickets
United Airlines
Feb 12
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
Feb 16
ORD8:50 amChicago O'Hare Intl
5h 26m
1 stop
YUL3:16 pmMontreal Pierre Elliott Trudeau Intl
$189
Find similar
United Airlines
Feb 5
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
3h 05m
ORD8:05 amChicago O'Hare Intl
Feb 8
ORD5:52 pmChicago O'Hare Intl
2h 25m
YUL9:17 pmMontreal Pierre Elliott Trudeau Intl
$190
Find similar
United Airlines
Feb 9
YUL9:15 amMontreal Pierre Elliott Trudeau Intl
6h 10m
1 stop
ORD2:25 pmChicago O'Hare Intl
Feb 18
ORD10:35 amChicago O'Hare Intl
2h 25m
YUL2:00 pmMontreal Pierre Elliott Trudeau Intl
$195
Find similar

Delta flights from Montreal to Chicago

Our best Delta deals on Montreal to Chicago flight tickets
Delta
Feb 5
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
8h 13m
1 stop
ORD1:13 pmChicago O'Hare Intl
Feb 8
ORD5:35 pmChicago O'Hare Intl
4h 51m
1 stop
YUL11:26 pmMontreal Pierre Elliott Trudeau Intl
$216
Find similar
Delta
Feb 13
YUL6:00 pmMontreal Pierre Elliott Trudeau Intl
6h 57m
1 stop
ORD11:57 pmChicago O'Hare Intl
Feb 15
ORD6:30 amChicago O'Hare Intl
4h 32m
1 stop
YUL12:02 pmMontreal Pierre Elliott Trudeau Intl
$224
Find similar
Delta
Feb 11
YUL12:50 pmMontreal Pierre Elliott Trudeau Intl
10h 32m
1 stop
MDW10:22 pmChicago Midway
Feb 15
MDW1:28 pmChicago Midway
8h 42m
1 stop
YUL11:10 pmMontreal Pierre Elliott Trudeau Intl
$259
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 832,500 searches. Data last updated December 18, 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 - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 2/12

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sat 2/14

12:45 pm-6:45 pm

1 stop5h 00m

$188

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 2/12

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 2/14

6:00 pm-9:17 pm

Nonstop2h 17m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 2/13

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Mon 2/16

4:15 pm-10:45 pm

1 stop5h 30m

$189

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 2/5

6:00 am-8:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Sun 2/8

5:52 pm-9:17 pm

Nonstop2h 25m

$190

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 2/6

3:50 pm-5:50 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 2/9

11:50 am-3:08 pm

Nonstop2h 18m

$193

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 2/6

3:50 pm-5:50 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 2/9

11:50 am-3:08 pm

Nonstop2h 18m

$194

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 2/9

9:15 am-2:25 pm

1 stop6h 10m

Chicago O'Hare Intl

Wed 2/18

10:35 am-2:00 pm

Nonstop2h 25m

$195

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 2/6

4:45 pm-6:51 pm

Nonstop3h 06m

Chicago O'Hare Intl

Mon 2/9

1:00 pm-7:48 pm

1 stop5h 48m

$196

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Tue 2/17

11:00 am-4:30 pm

1 stop4h 30m

$196

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 2/5

12:50 pm-10:22 pm

1 stop10h 32m

Chicago Midway

Sat 2/7

1:26 pm-11:12 pm

1 stop8h 46m

$216

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 September is, on average, the cheapest month to fly to Chicago from Montreal, with most prices found around $282. If you’re not able to fly to Chicago in September, then March is your next best option. Flight prices from Montreal to Chicago during March average around $283.

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 $434. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Montreal to Chicago for around $661.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Montreal to Chicago during this time can be as low as $471. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $524.

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 $354 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 $231 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 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

$233

Fastest flight time

2h 42m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Montreal in the past 72 hours is $233. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is $400.
The fastest flight from Montreal to Chicago takes 2h 42m
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?

    Montreal and Chicago are 744.2 mi apart from one another. 2h 42m 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 refresh daily.

  • 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 offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify 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
Air CanadaPriceFrom $156Free CancellationRating
7.1
10,534 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $217Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $251Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights

  • Porter Airlines Flights From Montreal to Chicago

    Porter Airlines flight deals from Montreal to Chicago start from $217 round-trip. Over the 6 Porter Airlines flights for this route in a normal week, average airfare is usually $300 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Montreal to Chicago

    United Airlines (7.4/10 from 9,093 reviews) operates around 32 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around $402, with deals from around $267 rare but found on momondo. Referenced prices are for round-trip Montreal to Chicago flight searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Montreal to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Montreal.

Can I find flights from Montreal to Chicago with flexible booking policies on momondo?

All flight searches from Montreal to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Montreal to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Montreal.

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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport