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Cheap flights from Montreal to Chicago from $100

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 4/23. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
6:25 pm - 8:10 pm
YUL
-
ORD
2h 45mnonstop
Air Canada Logo
12:50 pm - 4:01 pm
ORD
-
YUL
2h 11mnonstop
$177Air Canada
lun., feb. 23 - mié., feb. 25
Air Canada Logo
6:25 pm - 8:10 pm
YUL
-
ORD
2h 45mnonstop
Air Canada Logo
3:35 pm - 6:40 pm
ORD
-
YUL
2h 05mnonstop
$178Air Canada
mar., feb. 24 - mié., mar. 4
Porter Airlines Logo
11:25 am - 3:20 pm
YUL
-
MDW
4h 55m
1 stop
Porter Airlines Logo
4:15 pm - 10:45 pm
MDW
-
YUL
5h 30m
1 stop
$179Porter Airlines
mié., abr. 8 - dom., abr. 12
Porter Airlines Logo
10:35 am - 4:50 pm
YUL
-
MDW
7h 15m
1 stop
Porter Airlines Logo
10:25 am - 6:15 pm
MDW
-
YUL
6h 50m
1 stop
$180Porter Airlines
vie., may. 1 - lun., may. 4
United Airlines Logo
6:00 am - 8:00 am
YUL
-
ORD
3h 00mnonstop
United Airlines Logo
1:00 pm - 12:13 am
ORD
-
YUL
10h 13m
1 stop
$186United Airlines
jue., mar. 26 - lun., mar. 30
Porter Airlines Logo
6:45 am - 10:05 am
YUL
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 am - 6:15 pm
MDW
-
YUL
6h 15m
1 stop
$186Porter Airlines
mié., abr. 1 - mié., abr. 8
United Airlines Logo
4:45 pm - 6:45 pm
YUL
-
ORD
3h 00mnonstop
United Airlines Logo
6:01 pm - 12:13 am
ORD
-
YUL
5h 12m
1 stop
$187United Airlines
mar., mar. 10 - mar., mar. 31
American Airlines Logo
7:45 am - 11:34 pm
YUL
-
ORD
16h 49m
1 stop
American Airlines Logo
8:18 am - 11:44 am
ORD
-
YUL
2h 26mnonstop
$192American Airlines
mié., abr. 22 - sáb., abr. 25
Delta Logo
6:00 pm - 11:56 pm
YUL
-
ORD
6h 56m
1 stop
Delta Logo
5:25 am - 4:53 pm
ORD
-
YUL
10h 28m
1 stop
$209Delta
lun., feb. 23 - mié., feb. 25
Delta Logo
7:00 am - 1:25 pm
YUL
-
MDW
7h 25m
1 stop
Delta Logo
6:34 pm - 11:13 pm
MDW
-
YUL
3h 39m
1 stop
$218Delta
sáb., mar. 14 - lun., mar. 16

Air Canada flights from Montreal to Chicago

Our best Air Canada deals on Montreal to Chicago flight tickets
Air Canada
Feb 23
YUL6:25 pmMontreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 pmChicago O'Hare Intl
Feb 25
ORD12:50 pmChicago O'Hare Intl
2h 11m
YUL4:01 pmMontreal Pierre Elliott Trudeau Intl
$177
Air Canada
Feb 24
YUL6:25 pmMontreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 pmChicago O'Hare Intl
Mar 4
ORD3:35 pmChicago O'Hare Intl
2h 05m
YUL6:40 pmMontreal Pierre Elliott Trudeau Intl
$178
Air Canada
May 8
YUL6:30 pmMontreal Pierre Elliott Trudeau Intl
2h 38m
ORD8:08 pmChicago O'Hare Intl
May 15
ORD8:45 amChicago O'Hare Intl
2h 15m
YUL12:00 pmMontreal Pierre Elliott Trudeau Intl
$185

WestJet flights from Montreal to Chicago

Our best WestJet deals on Montreal to Chicago flight tickets
WestJet
Mar 15
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
9h 19m
1 stop
ORD3:19 pmChicago O'Hare Intl
Mar 17
ORD11:10 amChicago O'Hare Intl
5h 21m
1 stop
YUL5:31 pmMontreal Pierre Elliott Trudeau Intl
$258
WestJet
Jun 6
YUL12:40 pmMontreal Pierre Elliott Trudeau Intl
9h 29m
1 stop
MDW9:09 pmChicago Midway
Jun 11
MDW2:00 pmChicago Midway
8h 34m
1 stop
YUL11:34 pmMontreal Pierre Elliott Trudeau Intl
$315
WestJet
Feb 18
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
7h 35m
2 stops
ORD1:20 pmChicago O'Hare Intl
Feb 23
ORD5:37 pmChicago O'Hare Intl
4h 33m
1 stop
YUL11:10 pmMontreal Pierre Elliott Trudeau Intl
$434

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 febrero 4, 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 - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

lun. 2/23

6:25 pm-8:10 pm

Nonstop2h 45m

Chicago O'Hare Intl

mié. 2/25

12:50 pm-4:01 pm

Nonstop2h 11m

$177

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mar. 2/24

6:25 pm-8:10 pm

Nonstop2h 45m

Chicago O'Hare Intl

mié. 3/4

3:35 pm-6:40 pm

Nonstop2h 05m

$178

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 4/8

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

dom. 4/12

4:15 pm-10:45 pm

1 stop5h 30m

$179

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 5/1

10:35 am-4:50 pm

1 stop7h 15m

Chicago Midway

lun. 5/4

10:25 am-6:15 pm

1 stop6h 50m

$180

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

jue. 3/26

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

lun. 3/30

1:00 pm-12:13 am

1 stop10h 13m

$186

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 4/1

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

mié. 4/8

11:00 am-6:15 pm

1 stop6h 15m

$186

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mar. 3/10

4:45 pm-6:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

mar. 3/31

6:01 pm-12:13 am

1 stop5h 12m

$187

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mié. 4/22

7:45 am-11:34 pm

1 stop16h 49m

Chicago O'Hare Intl

sáb. 4/25

8:18 am-11:44 am

Nonstop2h 26m

$192

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

lun. 2/23

6:00 pm-11:56 pm

1 stop6h 56m

Chicago O'Hare Intl

mié. 2/25

5:25 am-4:53 pm

1 stop10h 28m

$209

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

sáb. 3/14

7:00 am-1:25 pm

1 stop7h 25m

Chicago Midway

lun. 3/16

6:34 pm-11:13 pm

1 stop3h 39m

$218

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 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 $280. 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 $430. 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 $663.

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 in the afternoon. Flights from Montreal to Chicago during this time can be as low as $493. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $522.

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 $352 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 $212 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 February 2026, prices for Montreal to Chicago flights are approximately 33% 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

$220

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 $220. The best round-trip flight deal from Montreal to Chicago found on momondo in the last 72 hours is $312.
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?

    Montreal and Chicago are 744.2 mi apart from one another. 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 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
10,688 reviews
Search Air Canada flights
American AirlinesPriceFrom $189Free CancellationRating
7.2
11,224 reviews
Search American Airlines flights
Porter AirlinesPriceFrom $217Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
9,236 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 7 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 9,236 reviews) operates around 33 flights from Montreal to Chicago in any given week. The average United Airlines airfare for this route is around $380, 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
Schererville
Valparaiso
Munster
Crown Point
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