Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Montreal to Chicago from C$ 144

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 26/4. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Montreal to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 213Porter Airlines
Thu, 30 Apr - Mon, 11 May
Porter Airlines Logo
9:50 a.m. - 3:20 p.m.
YUL
-
MDW
6h 30m
1 stop
Porter Airlines Logo
4:05 p.m. - 10:45 p.m.
MDW
-
YUL
5h 40m
1 stop
C$ 215Porter Airlines
Sun, 19 Apr - Fri, 24 Apr
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 216Porter Airlines
Thu, 30 Apr - Tue, 12 May
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
4:05 p.m. - 10:45 p.m.
MDW
-
YUL
5h 40m
1 stop
C$ 218Porter Airlines
Wed, 15 Apr - Fri, 24 Apr
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
3:20 p.m. - 8:10 p.m.
MDW
-
YUL
3h 50m
1 stop
C$ 223Porter Airlines
Fri, 8 May - Sun, 10 May
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:15 p.m.
MDW
-
YUL
6h 50m
1 stop
C$ 224Porter Airlines
Thu, 30 Apr - Mon, 11 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$ 226Porter Airlines
Thu, 4 Jun - Mon, 8 Jun
Porter Airlines Logo
6:50 a.m. - 10:05 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 228Porter Airlines
Thu, 26 Mar - Mon, 30 Mar
Porter Airlines Logo
11:45 a.m. - 3:20 p.m.
YUL
-
MDW
4h 35m
1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m
1 stop
C$ 231Porter Airlines
Fri, 17 Apr - Mon, 20 Apr
Porter Airlines Logo
6:50 a.m. - 10:05 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 233Porter Airlines
Thu, 26 Mar - Mon, 30 Mar

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
30 Apr
YUL6:50 a.m.Montreal Pierre Elliott Trudeau Intl
4h 25m
1 stop
MDW10:15 a.m.Chicago Midway
11 May
MDW10:25 a.m.Chicago Midway
5h 50m
1 stop
YUL5:15 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 213
Porter Airlines
19 Apr
YUL9:50 a.m.Montreal Pierre Elliott Trudeau Intl
6h 30m
1 stop
MDW3:20 p.m.Chicago Midway
24 Apr
MDW4:05 p.m.Chicago Midway
5h 40m
1 stop
YUL10:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 215
Porter Airlines
30 Apr
YUL6:50 a.m.Montreal Pierre Elliott Trudeau Intl
4h 25m
1 stop
MDW10:15 a.m.Chicago Midway
12 May
MDW3:20 p.m.Chicago Midway
5h 50m
1 stop
YUL10:10 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 216

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
23 Apr
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 43m
1 stop
MDW12:43 p.m.Chicago Midway
2 May
MDW5:21 p.m.Chicago Midway
5h 30m
1 stop
YUL11:51 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 283
Delta
22 Apr
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
10h 26m
1 stop
MDW4:26 p.m.Chicago Midway
25 Apr
MDW1:24 p.m.Chicago Midway
8h 44m
1 stop
YUL11:08 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 298
Delta
6 Jun
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 42m
1 stop
MDW12:42 p.m.Chicago Midway
12 Jun
MDW2:00 p.m.Chicago Midway
8h 34m
1 stop
YUL11:34 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 300

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 4 March 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

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 30/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Mon 11/5

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

1 stop5h 50m

C$ 213

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 19/4

9:50 a.m.-3:20 p.m.

1 stop6h 30m

Chicago Midway

Fri 24/4

4:05 p.m.-10:45 p.m.

1 stop5h 40m

C$ 215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 30/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Tue 12/5

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

1 stop5h 50m

C$ 216

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Fri 24/4

4:05 p.m.-10:45 p.m.

1 stop5h 40m

C$ 218

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 8/5

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

1 stop4h 10m

Chicago Midway

Sun 10/5

3:20 p.m.-8:10 p.m.

1 stop3h 50m

C$ 223

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 30/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Mon 11/5

10:25 a.m.-6:15 p.m.

1 stop6h 50m

C$ 224

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 4/6

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

1 stop5h 00m

Chicago Midway

Mon 8/6

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

1 stop5h 50m

C$ 226

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/3

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Mon 30/3

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 228

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/4

11:45 a.m.-3:20 p.m.

1 stop4h 35m

Chicago Midway

Mon 20/4

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

1 stop4h 30m

C$ 231

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/3

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Mon 30/3

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 233

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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

  • 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$ 187Free CancellationRating
8.0
421 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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 3/4
Fri 10/4
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago