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Cheap flights from Montreal to Chicago from C$ 226

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 20/5. 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.
Porter Airlines Logo
10:15 a.m. - 3:20 p.m.YUL-MDW
6h 05m1 stop
Porter Airlines Logo
12:45 p.m. - 6:45 p.m.MDW-YUL
5h 00m1 stop
C$ 271Porter Airlines
Find Deal
Tue, 14 Apr - Sat, 18 Apr
Porter Airlines Logo
6:45 a.m. - 10:10 a.m.YUL-MDW
4h 25m1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.MDW-YUL
5h 30m1 stop
C$ 273Porter Airlines
Find Deal
Fri, 27 Feb - Sun, 8 Mar
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.YUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.MDW-YUL
6h 45m1 stop
C$ 274Porter Airlines
Find Deal
Sat, 27 Dec - Mon, 23 Feb
Porter Airlines Logo
11:25 a.m. - 3:20 p.m.YUL-MDW
4h 55m1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.MDW-YUL
5h 30m1 stop
C$ 278Porter Airlines
Find Deal
Wed, 18 Mar - Mon, 23 Mar
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.YUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.MDW-YUL
6h 45m1 stop
C$ 280Porter Airlines
Find Deal
Mon, 22 Dec - Tue, 30 Dec
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.YUL-MDW
4h 20m1 stop
Porter Airlines Logo
12:45 p.m. - 6:45 p.m.MDW-YUL
5h 00m1 stop
C$ 281Porter Airlines
Find Deal
Thu, 5 Mar - Sat, 7 Mar
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$ 284Porter Airlines
Find Deal
Wed, 18 Feb - Sun, 22 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$ 287Porter Airlines
Find Deal
Fri, 27 Feb - Sun, 8 Mar
Porter Airlines Logo
11:25 a.m. - 3:20 p.m.YUL-MDW
4h 55m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.MDW-YUL
4h 30m1 stop
C$ 294Porter Airlines
Find Deal
Sun, 12 Apr - Thu, 16 Apr
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.YUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.MDW-YUL
6h 45m1 stop
C$ 295Porter Airlines
Find Deal
Sat, 27 Dec - Mon, 23 Feb

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
14 Apr
YUL10:15 a.m.Montreal Pierre Elliott Trudeau Intl
6h 05m
1 stop
MDW3:20 p.m.Chicago Midway
18 Apr
MDW12:45 p.m.Chicago Midway
5h 00m
1 stop
YUL6:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 271
Find similar
Porter Airlines
27 Feb
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 25m
1 stop
MDW10:10 a.m.Chicago Midway
8 Mar
MDW4:15 p.m.Chicago Midway
5h 30m
1 stop
YUL10:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 273
Find similar
Porter Airlines
27 Dec
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
23 Feb
MDW11:00 a.m.Chicago Midway
6h 45m
1 stop
YUL6:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 274
Find similar

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
14 Jan
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 48m
1 stop
MDW12:48 p.m.Chicago Midway
21 Jan
MDW10:46 a.m.Chicago Midway
5h 09m
1 stop
YUL4:55 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 309
Find similar
Delta
2 Mar
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 p.m.Chicago Midway
3 Mar
MDW6:17 p.m.Chicago Midway
3h 53m
1 stop
YUL11:10 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 310
Find similar
Delta
14 Dec
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 34m
1 stop
MDW12:34 p.m.Chicago Midway
15 Dec
MDW12:50 p.m.Chicago Midway
10h 09m
1 stop
YUL11:59 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 354
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montreal to Chicago Midway Airport 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 2 December 2025.
Use the filters below to find and compare flights from Montreal to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 14/4

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

1 stop6h 05m

Chicago Midway

Sat 18/4

12:45 p.m.-6:45 p.m.

1 stop5h 00m

C$ 271

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 27/2

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

1 stop4h 25m

Chicago Midway

Sun 8/3

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

1 stop5h 30m

C$ 273

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 27/12

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

1 stop4h 20m

Chicago Midway

Mon 23/2

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

1 stop6h 45m

C$ 274

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/3

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Mon 23/3

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

1 stop5h 30m

C$ 278

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 22/12

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

1 stop4h 20m

Chicago Midway

Tue 30/12

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

1 stop6h 45m

C$ 280

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 5/3

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

1 stop4h 20m

Chicago Midway

Sat 7/3

12:45 p.m.-6:45 p.m.

1 stop5h 00m

C$ 281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/2

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

1 stop4h 20m

Chicago Midway

Sun 22/2

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

1 stop5h 30m

C$ 284

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 27/2

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

1 stop4h 20m

Chicago Midway

Sun 8/3

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

1 stop5h 30m

C$ 287

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 12/4

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Thu 16/4

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

1 stop4h 30m

C$ 294

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 27/12

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

1 stop4h 20m

Chicago Midway

Mon 23/2

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

1 stop6h 45m

C$ 295

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 Midway Airport

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 day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Tuesday when prices can be found for as low as C$ 357. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Montreal because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 515.

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

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the afternoon. Flights from Montreal to Chicago Midway Airport during this time can be as low as C$ 387. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 410.

When to book flights from Montreal to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montreal to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montreal to Chicago Midway Airport (YMQ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montreal to Chicago Midway Airport

Fastest flight time

4h 14m

Direct flights

None
The fastest flight from Montreal to Chicago Midway Airport takes 4h 14m
There are no direct flights from Montreal to Chicago Midway Airport. There are no popular flight routes from Montreal to Chicago Midway Airport.
Search flight deals

  • How far is Montreal to Chicago Midway by plane?

    A flight from Montreal to Chicago Midway will travel around 1210.7 km. Typically, this will take 4h 20m by plane in normal conditions.

  • When did momondo last update prices for flights from Montreal to Chicago Midway Airport?

    Prices for flights from Montreal to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Montreal to Chicago Midway Airport?

  • How old do you have to be to fly from Montreal to Chicago Midway Airport?

    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 Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Montreal to Chicago Midway Airport?

Best airlines flying from Montreal to Chicago Midway Airport

Compare and see reviews for airlines that fly from Montreal to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 199Free CancellationRating
8.0
394 reviews
Search Porter Airlines flights

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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Montreal to Chicago for you.

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

Flights from Montreal to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Montreal to Chicago.

I’m not ready to book a flight from Montreal to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Montreal to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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