Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Montreal to Chicago from C$ 230

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 29/7. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Montreal to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:15 p.m. - 10:10 p.m.
MDW
-
YUL
5h 55m
1 stop
C$ 380Porter Airlines
Mon, 17 Aug - Tue, 18 Aug
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:15 p.m. - 8:10 p.m.
MDW
-
YUL
3h 55m
1 stop
C$ 383Porter Airlines
Wed, 5 Aug - Tue, 11 Aug
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
3:20 p.m. - 9:12 p.m.
MDW
-
YUL
4h 52m
1 stop
C$ 384Porter Airlines
Sat, 26 Sep - Wed, 30 Sep
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:10 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 386Porter Airlines
Fri, 14 Aug - Tue, 18 Aug
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:15 p.m. - 10:10 p.m.
MDW
-
YUL
5h 55m
1 stop
C$ 387Porter Airlines
Wed, 12 Aug - Wed, 19 Aug
Delta Logo
6:00 a.m. - 12:33 p.m.
YUL
-
MDW
7h 33m
1 stop
Delta Logo
9:30 a.m. - 3:59 p.m.
MDW
-
YUL
5h 29m
1 stop
C$ 388Delta
Tue, 12 Jan - Sat, 23 Jan
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:10 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 390Porter Airlines
Tue, 28 Jul - Tue, 18 Aug
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:10 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 391Porter Airlines
Mon, 10 Aug - Tue, 18 Aug
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:15 p.m. - 8:10 p.m.
MDW
-
YUL
3h 55m
1 stop
C$ 393Porter Airlines
Thu, 13 Aug - Mon, 17 Aug
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:15 p.m. - 10:10 p.m.
MDW
-
YUL
5h 55m
1 stop
C$ 395Porter Airlines
Tue, 11 Aug - Wed, 12 Aug

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

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
12 Jan
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 33m
1 stop
MDW12:33 p.m.Chicago Midway
23 Jan
MDW9:30 a.m.Chicago Midway
5h 29m
1 stop
YUL3:59 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 388
Delta
22 Aug
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 39m
1 stop
MDW12:39 p.m.Chicago Midway
23 Aug
MDW6:42 p.m.Chicago Midway
3h 48m
1 stop
YUL11:30 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 412
Delta
22 Aug
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
4h 17m
1 stop
MDW9:17 a.m.Chicago Midway
23 Aug
MDW6:42 p.m.Chicago Midway
3h 48m
1 stop
YUL11:30 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 414

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
17 Aug
YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl
4h 15m
1 stop
MDW9:45 a.m.Chicago Midway
18 Aug
MDW3:15 p.m.Chicago Midway
5h 55m
1 stop
YUL10:10 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 380
Porter Airlines
5 Aug
YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl
4h 15m
1 stop
MDW9:45 a.m.Chicago Midway
11 Aug
MDW3:15 p.m.Chicago Midway
3h 55m
1 stop
YUL8:10 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 383
Porter Airlines
26 Sep
YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl
5h 30m
1 stop
MDW11:00 a.m.Chicago Midway
30 Sep
MDW3:20 p.m.Chicago Midway
4h 52m
1 stop
YUL9:12 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 384

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 19 July 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

Mon 17/8

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

1 stop4h 15m

Chicago Midway

Tue 18/8

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

1 stop5h 55m

C$ 380
Quickest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 5/8

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

1 stop4h 15m

Chicago Midway

Tue 11/8

3:15 p.m.-8:10 p.m.

1 stop3h 55m

C$ 383

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 26/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Wed 30/9

3:20 p.m.-9:12 p.m.

1 stop4h 52m

C$ 384

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 14/8

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

1 stop5h 00m

Chicago Midway

Tue 18/8

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

1 stop6h 45m

C$ 386

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 12/8

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

1 stop4h 15m

Chicago Midway

Wed 19/8

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

1 stop5h 55m

C$ 387

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 12/1

6:00 a.m.-12:33 p.m.

1 stop7h 33m

Chicago Midway

Sat 23/1

9:30 a.m.-3:59 p.m.

1 stop5h 29m

C$ 388

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 28/7

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

1 stop5h 00m

Chicago Midway

Tue 18/8

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

1 stop6h 45m

C$ 390

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 10/8

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

1 stop4h 15m

Chicago Midway

Tue 18/8

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

1 stop6h 45m

C$ 391

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 13/8

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

1 stop4h 15m

Chicago Midway

Mon 17/8

3:15 p.m.-8:10 p.m.

1 stop3h 55m

C$ 393

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 11/8

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

1 stop4h 15m

Chicago Midway

Wed 12/8

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

1 stop5h 55m

C$ 395

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 cheapest month to fly to Chicago Midway Airport?

In general, January is the cheapest month to fly from Montreal to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 0. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Montreal during the month May is also very affordable. Most momondo users find prices during this month for around C$ 245.

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$ 245Free CancellationRating
8.0
445 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
Valparaiso
Portage

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
Tue 18/8
Tue 25/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago