What is the cheapest airline that flies from Montreal to Chicago Midway?

Porter Airlines, Delta, and WestJet are the most popular carriers operating from Montreal to Chicago Midway

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

Prices for flights from Montreal to Chicago Midway Airport refresh daily.

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

As of February 2025, there is 1 operator available to choose from 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 a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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.

$139 Cheap Flights from Montreal to Chicago Midway Airport in 2025

Q: What is the typical price of a round-trip flight between Montreal and Chicago Midway Airport?

Prices are currently low for flights on this route. Typical prices usually range from $284 to $346. The lowest price recently found on this route was $215.

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Find the cheapest flights from Montreal to Chicago

Round-trip

One-way

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Cheap round-trip flights

These are some of the best round-trip flight deals from Montreal to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

6:50 am - 10:20 amYUL-MDW

4h 30m1 stop

11:15 am - 4:50 pmMDW-YUL

4h 35m1 stop

$215Porter Airlines

Find Deal

Thu, Mar 27 - Sun, Mar 30

11:50 am - 4:40 pmYUL-MDW

5h 50m1 stop

5:35 pm - 10:47 pmMDW-YUL

4h 12m1 stop

$216Porter Airlines

Find Deal

Fri, Apr 4 - Wed, Apr 9

6:50 am - 10:20 amYUL-MDW

4h 30m1 stop

11:15 am - 4:50 pmMDW-YUL

4h 35m1 stop

$217Porter Airlines

Find Deal

Thu, Mar 27 - Sun, Mar 30

11:50 am - 4:40 pmYUL-MDW

5h 50m1 stop

11:15 am - 6:02 pmMDW-YUL

5h 47m1 stop

$224Porter Airlines

Find Deal

Fri, Apr 4 - Mon, Apr 7

6:00 am - 12:30 pmYUL-MDW

7h 30m1 stop

5:59 pm - 11:08 pmMDW-YUL

4h 09m1 stop

$276Delta

Find Deal

Sat, May 24 - Sat, May 31

7:05 am - 12:36 pmYUL-MDW

6h 31m1 stop

6:42 pm - 11:26 pmMDW-YUL

3h 44m1 stop

$277Delta

Find Deal

Thu, Mar 27 - Sun, Mar 30

6:05 am - 2:15 pmYUL-MDW

9h 10m1 stop

12:55 pm - 6:15 pmMDW-YUL

4h 20m1 stop

$316

Find Deal

Fri, Mar 21 - Sat, Mar 22

6:05 am - 10:47 amYUL-MDW

5h 42m1 stop

12:55 pm - 6:15 pmMDW-YUL

4h 20m1 stop

$342

Find Deal

Sat, Mar 22 - Sat, Mar 29

3:00 pm - 1:05 pmYUL-MDW

23h 05m1 stop

6:45 pm - 11:18 pmMDW-YUL

27h 33m1 stop

$343WestJet

Find Deal

Fri, Jun 6 - Mon, Jun 9

6:45 am - 9:07 amYUL-MDW

27h 22m2 stops

12:48 pm - 4:42 pmMDW-YUL

26h 54m1 stop

$356WestJet

Find Deal

Fri, Apr 25 - Tue, Apr 29

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets

Porter Airlines

Mar 27

YUL6:50 amMontreal Pierre Elliott Trudeau Intl

4h 30m

1 stop

MDW10:20 amChicago Midway

Mar 30

MDW11:15 amChicago Midway

4h 35m

1 stop

YUL4:50 pmMontreal Pierre Elliott Trudeau Intl

$215

Find similar

Porter Airlines

Apr 4

YUL11:50 amMontreal Pierre Elliott Trudeau Intl

5h 50m

1 stop

MDW4:40 pmChicago Midway

Apr 9

MDW5:35 pmChicago Midway

4h 12m

1 stop

YUL10:47 pmMontreal Pierre Elliott Trudeau Intl

$216

Find similar

Porter Airlines

Mar 27

YUL6:50 amMontreal Pierre Elliott Trudeau Intl

4h 30m

1 stop

MDW10:20 amChicago Midway

Mar 30

MDW11:15 amChicago Midway

4h 35m

1 stop

YUL4:50 pmMontreal Pierre Elliott Trudeau Intl

$217

Find similar

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets

Delta

May 24

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

7h 30m

1 stop

MDW12:30 pmChicago Midway

May 31

MDW5:59 pmChicago Midway

4h 09m

1 stop

YUL11:08 pmMontreal Pierre Elliott Trudeau Intl

$276

Find similar

Delta

Mar 27

YUL7:05 amMontreal Pierre Elliott Trudeau Intl

6h 31m

1 stop

MDW12:36 pmChicago Midway

Mar 30

MDW6:42 pmChicago Midway

3h 44m

1 stop

YUL11:26 pmMontreal Pierre Elliott Trudeau Intl

$277

Find similar

Delta

May 26

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

7h 30m

1 stop

MDW12:30 pmChicago Midway

May 28

MDW1:05 pmChicago Midway

9h 53m

1 stop

YUL11:58 pmMontreal Pierre Elliott Trudeau Intl

$285

Find similar

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

Prices

Airlines

What is the typical price of a round-trip flight between Montreal and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Montreal, with most prices found around $267. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Montreal during the month July is also very affordable. Most momondo users find prices during this month for around $270.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Montreal. The lowest ticket price found for a Friday departure recently was $277. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Montreal because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $346.

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

Flying to Chicago Midway Airport from Montreal in the morning is the least expensive time of day to depart. momondo users have found prices as low as $325 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $384. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Best Price Found	$139
Fastest flight time	4h 14m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Montreal in the past 72 hours is $139. The best round-trip flight deal from Montreal to Chicago Midway Airport found on momondo in the last 72 hours is $215.

The fastest flight from Montreal to Chicago Midway Airport takes 4h 14m

There are no direct flights from Montreal to Chicago Midway Airport. Popular non-direct route for this connection is Montreal Pierre Elliott Trudeau Intl Airport - Chicago Midway Airport.

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How far is Montreal to Chicago Midway by plane?
There are 752.3 mi between Montreal and Chicago Midway. 4h 14m is a normal flight duration for this route.
When did momondo last update prices for flights from Montreal to Chicago Midway Airport?
Prices for flights from Montreal to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Montreal to Chicago Midway Airport?
As of February 2025, there is 1 operator available to choose from 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 a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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?
Based on momondo bookings for flights between Montreal and Chicago Midway Airport, the leading airline is Porter Airlines, making up 100% of the total bookings.

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 Airlines	PriceFrom $267	Free Cancellation	Rating 7.9 277 reviews		Search Porter Airlines flights

Merrillville

Hammond

New Buffalo

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Munster

Crown Point

Schererville

Monticello

Chesterton

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Montreal to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Montreal to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from Montreal with this policy.

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

momondo helps you find the best flight between Montreal and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Chicago from Montreal. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.