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Cheap flights from Montreal to Chicago from C$ 158

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 28/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 248Porter Airlines
Wed, 3 Jun - Sun, 7 Jun
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:30 a.m. - 5:15 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 249Porter Airlines
Thu, 28 May - Fri, 29 May
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 278Porter Airlines
Tue, 26 May - Tue, 2 Jun
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:30 a.m. - 6:15 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 306Porter Airlines
Sun, 3 May - Mon, 4 May
Porter Airlines Logo
6:30 a.m. - 2:35 p.m.
YUL
-
MDW
9h 05m
1 stop
Porter Airlines Logo
10:30 a.m. - 8:10 p.m.
MDW
-
YUL
8h 40m
1 stop
C$ 308Porter Airlines
Thu, 7 May - Sun, 10 May
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:30 a.m. - 6:15 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 311Porter Airlines
Fri, 22 May - Mon, 25 May
Porter Airlines Logo
6:30 a.m. - 2:35 p.m.
YUL
-
MDW
9h 05m
1 stop
Porter Airlines Logo
10:30 a.m. - 8:10 p.m.
MDW
-
YUL
8h 40m
1 stop
C$ 313Porter Airlines
Thu, 7 May - Sun, 10 May
Porter Airlines Logo
6:30 a.m. - 2:35 p.m.
YUL
-
MDW
9h 05m
1 stop
Porter Airlines Logo
10:30 a.m. - 8:10 p.m.
MDW
-
YUL
8h 40m
1 stop
C$ 315Porter Airlines
Thu, 7 May - Sun, 10 May
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 322Porter Airlines
Fri, 29 May - Mon, 1 Jun
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 340Porter Airlines
Thu, 4 Jun - Thu, 11 Jun

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
3 Jun
YUL10:35 a.m.Montreal Pierre Elliott Trudeau Intl
5h 00m
1 stop
MDW2:35 p.m.Chicago Midway
7 Jun
MDW10:25 a.m.Chicago Midway
5h 50m
1 stop
YUL5:15 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 248
Porter Airlines
28 May
YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl
4h 15m
1 stop
MDW9:45 a.m.Chicago Midway
29 May
MDW10:30 a.m.Chicago Midway
5h 45m
1 stop
YUL5:15 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 249
Porter Airlines
4 Jun
YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl
4h 10m
1 stop
MDW9:40 a.m.Chicago Midway
7 Jun
MDW10:25 a.m.Chicago Midway
5h 50m
1 stop
YUL5:15 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 250

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
6 Jun
YUL12:49 p.m.Montreal Pierre Elliott Trudeau Intl
6h 44m
1 stop
MDW6:33 p.m.Chicago Midway
11 Jun
MDW1:16 p.m.Chicago Midway
9h 12m
1 stop
YUL11:28 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 427
Delta
27 Apr
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
10h 26m
1 stop
MDW4:26 p.m.Chicago Midway
16 May
MDW6:36 p.m.Chicago Midway
3h 37m
1 stop
YUL11:13 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 541
Delta
17 Apr
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
10h 29m
1 stop
MDW4:29 p.m.Chicago Midway
20 Apr
MDW12:52 p.m.Chicago Midway
9h 59m
1 stop
YUL11:51 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 596

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 14 April 2026.
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

Cheapest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 3/6

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

1 stop5h 00m

Chicago Midway

Sun 7/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 248
Quickest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 28/5

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Fri 29/5

10:30 a.m.-5:15 p.m.

1 stop5h 45m

C$ 249

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 26/5

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

1 stop5h 00m

Chicago Midway

Tue 2/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 278

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 3/5

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

1 stop5h 00m

Chicago Midway

Mon 4/5

10:30 a.m.-6:15 p.m.

1 stop6h 45m

C$ 306

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/5

6:30 a.m.-2:35 p.m.

1 stop9h 05m

Chicago Midway

Sun 10/5

10:30 a.m.-8:10 p.m.

1 stop8h 40m

C$ 308

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 22/5

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Mon 25/5

10:30 a.m.-6:15 p.m.

1 stop6h 45m

C$ 311

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/5

6:30 a.m.-2:35 p.m.

1 stop9h 05m

Chicago Midway

Sun 10/5

10:30 a.m.-8:10 p.m.

1 stop8h 40m

C$ 313

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/5

6:30 a.m.-2:35 p.m.

1 stop9h 05m

Chicago Midway

Sun 10/5

10:30 a.m.-8:10 p.m.

1 stop8h 40m

C$ 315

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 29/5

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Mon 1/6

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

1 stop5h 50m

C$ 322

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 4/6

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Thu 11/6

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

1 stop5h 50m

C$ 340

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Montreal and Chicago Midway Airport?

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 10m

Direct flights

None
The fastest flight from Montreal to Chicago Midway Airport takes 4h 10m
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

Frequently asked questions about flying from Montreal to Chicago Midway Airport

  • 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 10m 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$ 181Free CancellationRating
8.0
435 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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

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.

An easier way to manage your Chicago Midway Airport trip

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