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Cheap flights from Montreal to Chicago from C$ 190

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 30/9. 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

Delta Logo
7:00 a.m. - 4:09 p.m.YUL-MDW
10h 09m1 stop
Delta Logo
5:04 p.m. - 11:48 p.m.MDW-YUL
5h 44m1 stop
C$ 297Delta
Find Deal
Wed, 22 Oct - Tue, 28 Oct
Delta Logo
10:57 a.m. - 5:35 p.m.YUL-MDW
7h 38m1 stop
Delta Logo
6:15 p.m. - 11:29 p.m.MDW-YUL
4h 14m1 stop
C$ 325Delta
Find Deal
Sat, 27 Sep - Mon, 29 Sep
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 a.m. - 4:00 p.m.MDW-YUL
5h 25m1 stop
C$ 326Porter Airlines
Find Deal
Thu, 11 Sep - Sun, 14 Sep
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 328Porter Airlines
Find Deal
Thu, 11 Sep - Sun, 14 Sep
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
9:35 a.m. - 4:00 p.m.MDW-YUL
5h 25m1 stop
C$ 329Porter Airlines
Find Deal
Fri, 12 Sep - Sun, 14 Sep
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 331Porter Airlines
Find Deal
Tue, 16 Sep - Sun, 21 Sep
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 332Porter Airlines
Find Deal
Thu, 18 Sep - Mon, 22 Sep
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 333Porter Airlines
Find Deal
Thu, 4 Sep - Tue, 9 Sep
Delta Logo
7:00 a.m. - 11:48 a.m.YUL-MDW
5h 48m1 stop
Delta Logo
12:43 p.m. - 11:56 p.m.MDW-YUL
10h 13m1 stop
C$ 349Delta
Find Deal
Tue, 16 Sep - Tue, 23 Sep
Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Logo
9:32 a.m. - 10:10 p.m.MDW-YUL
11h 38m2 stops
C$ 407
Find Deal
Tue, 7 Oct - Fri, 31 Oct

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
11 Sep
YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl
4h 14m
1 stop
MDW4:24 p.m.Chicago Midway
14 Sep
MDW9:35 a.m.Chicago Midway
5h 25m
1 stop
YUL4:00 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 326
Find similar
Porter Airlines
11 Sep
YUL10:45 a.m.Montreal Pierre Elliott Trudeau Intl
6h 39m
1 stop
MDW4:24 p.m.Chicago Midway
14 Sep
MDW5:20 p.m.Chicago Midway
3h 55m
1 stop
YUL10:15 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 328
Find similar
Porter Airlines
12 Sep
YUL10:45 a.m.Montreal Pierre Elliott Trudeau Intl
6h 39m
1 stop
MDW4:24 p.m.Chicago Midway
14 Sep
MDW9:35 a.m.Chicago Midway
5h 25m
1 stop
YUL4:00 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 329
Find similar

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
22 Oct
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
10h 09m
1 stop
MDW4:09 p.m.Chicago Midway
28 Oct
MDW5:04 p.m.Chicago Midway
5h 44m
1 stop
YUL11:48 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 297
Find similar
Delta
27 Sep
YUL10:57 a.m.Montreal Pierre Elliott Trudeau Intl
7h 38m
1 stop
MDW5:35 p.m.Chicago Midway
29 Sep
MDW6:15 p.m.Chicago Midway
4h 14m
1 stop
YUL11:29 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 325
Find similar
Delta
16 Sep
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
5h 48m
1 stop
MDW11:48 a.m.Chicago Midway
23 Sep
MDW12:43 p.m.Chicago Midway
10h 13m
1 stop
YUL11:56 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 349
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 20 August 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

Wed 22/10

7:00 a.m.-4:09 p.m.

1 stop10h 09m

Chicago Midway

Tue 28/10

5:04 p.m.-11:48 p.m.

1 stop5h 44m

C$ 297

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 27/9

10:57 a.m.-5:35 p.m.

1 stop7h 38m

Chicago Midway

Mon 29/9

6:15 p.m.-11:29 p.m.

1 stop4h 14m

C$ 325

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/9

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Sun 14/9

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 326

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/9

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Sun 14/9

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 328

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 12/9

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Sun 14/9

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 329

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 16/9

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Sun 21/9

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 331

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 18/9

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Mon 22/9

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 332

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 4/9

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Tue 9/9

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 333

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 16/9

7:00 a.m.-11:48 a.m.

1 stop5h 48m

Chicago Midway

Tue 23/9

12:43 p.m.-11:56 p.m.

1 stop10h 13m

C$ 349

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 7/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Fri 31/10

9:32 a.m.-10:10 p.m.

2 stops11h 38m

C$ 407

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$ 353. 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$ 510.

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$ 383. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 405.

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

Direct flights

None
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 14m 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$ 203Free CancellationRating
8.0
336 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond
Munster
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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