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

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

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

As of September 2026, 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 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.

C$ 228 Cheap Flights from Montreal to Chicago Midway Airport in 2026

Find the cheapest flights from Montreal to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 388Porter Airlines

Sat, 3 Oct - Sat, 10 Oct

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

3:20 p.m. - 9:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 52m1 stop Toronto Island

C$ 388Porter Airlines

Sat, 3 Oct - Wed, 7 Oct

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 388Porter Airlines

Sat, 19 Sep - Sat, 26 Sep

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

3:20 p.m. - 9:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 52m1 stop Toronto Island

C$ 388Porter Airlines

Tue, 22 Sep - Wed, 23 Sep

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 388Porter Airlines

Sat, 26 Sep - Mon, 28 Sep

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 390Porter Airlines

Sat, 3 Oct - Sat, 10 Oct

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 391Porter Airlines

Wed, 23 Sep - Sat, 26 Sep

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 393Porter Airlines

Sat, 26 Sep - Sun, 27 Sep

6:00 a.m. - 12:47 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

7h 47m1 stop Detroit Metropolitan Wayne County

6:44 p.m. - 11:25 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 41m1 stop Detroit Metropolitan Wayne County

C$ 410Delta

Wed, 28 Oct - Thu, 29 Oct

6:00 a.m. - 12:51 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

7h 51m1 stop Detroit Metropolitan Wayne County

1:31 p.m. - 11:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

8h 56m1 stop Detroit Metropolitan Wayne County

C$ 415Delta

Tue, 17 Nov - Sun, 22 Nov

Cheap last-minute flights

Enter your travel dates to find the best prices.

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 485Porter Airlines

Sat, 12 Sep - Sat, 26 Sep

9:00 a.m. - 2:35 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 35m1 stop Toronto Island

3:20 p.m. - 9:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 52m1 stop Toronto Island

C$ 605Porter Airlines

Fri, 11 Sep - Fri, 18 Sep

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

3:20 p.m. - 9:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 52m1 stop Toronto Island

C$ 621Porter Airlines

Fri, 11 Sep - Tue, 15 Sep

9:00 a.m. - 2:35 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 35m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 627Porter Airlines

Wed, 9 Sep - Mon, 14 Sep

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

3:20 p.m. - 9:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 52m1 stop Toronto Island

C$ 634Porter Airlines

Fri, 11 Sep - Tue, 15 Sep

9:00 a.m. - 2:35 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 35m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 654Porter Airlines

Wed, 9 Sep - Fri, 11 Sep

9:00 a.m. - 2:35 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 35m1 stop Toronto Island

11:45 a.m. - 6:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 27m1 stop Toronto Island

C$ 658Porter Airlines

Thu, 10 Sep - Sat, 12 Sep

6:30 a.m. - 11:00 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

5h 30m1 stop Toronto Island

3:20 p.m. - 9:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 52m1 stop Toronto Island

C$ 665Porter Airlines

Sat, 12 Sep - Sun, 13 Sep

7:00 a.m. - 4:15 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

10h 15m1 stop Atlanta Hartsfield-Jackson

5:10 p.m. - 11:50 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 40m1 stop Atlanta Hartsfield-Jackson

C$ 940Delta

Sun, 13 Sep - Mon, 14 Sep

8:00 p.m. - 5:51 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

22h 51m2 stops Calgary Atlanta Hartsfield-Jackson

3:20 p.m. - 9:12 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 52m1 stop Toronto Island

C$ 1,024Multiple Airlines

Fri, 11 Sep - Tue, 15 Sep

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Delta flights from Montreal to Chicago Midway Airport

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

Delta

17 Nov

YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl

7h 51m

1 stop

MDW12:51 p.m.Chicago Midway

23 Nov

MDW1:31 p.m.Chicago Midway

8h 56m

1 stop

YUL11:27 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 415

Delta

22 Oct

YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl

4h 32m

1 stop

MDW9:32 a.m.Chicago Midway

31 Oct

MDW6:44 p.m.Chicago Midway

3h 41m

1 stop

YUL11:25 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 431

Delta

21 Oct

YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl

7h 47m

1 stop

MDW12:47 p.m.Chicago Midway

28 Oct

MDW9:29 a.m.Chicago Midway

5h 46m

1 stop

YUL4:15 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 434

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 Oct

YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl

5h 30m

1 stop

MDW11:00 a.m.Chicago Midway

10 Oct

MDW11:45 a.m.Chicago Midway

5h 27m

1 stop

YUL6:12 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 388

Porter Airlines

3 Oct

YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl

5h 30m

1 stop

MDW11:00 a.m.Chicago Midway

10 Oct

MDW11:45 a.m.Chicago Midway

5h 27m

1 stop

YUL6:12 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 390

Porter Airlines

23 Sep

YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl

5h 30m

1 stop

MDW11:00 a.m.Chicago Midway

26 Sep

MDW11:45 a.m.Chicago Midway

5h 27m

1 stop

YUL6:12 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 391

momondo Fare Finder

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 Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 3/10

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

1 stop5h 30m

Chicago Midway

Sat 10/10

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 388

Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 3/10

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

1 stop5h 30m

Chicago Midway

Wed 7/10

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

1 stop4h 52m

C$ 388

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 19/9

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

1 stop5h 30m

Chicago Midway

Sat 26/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 388

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 22/9

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

1 stop5h 30m

Chicago Midway

Wed 23/9

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

1 stop4h 52m

C$ 388

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 26/9

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

1 stop5h 30m

Chicago Midway

Mon 28/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 388

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 3/10

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

1 stop5h 30m

Chicago Midway

Sat 10/10

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 390

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 23/9

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

1 stop5h 30m

Chicago Midway

Sat 26/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 391

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 26/9

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

1 stop5h 30m

Chicago Midway

Sun 27/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 393

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 28/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

Chicago Midway

Thu 29/10

6:44 p.m.-11:25 p.m.

1 stop3h 41m

C$ 410

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 17/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Sun 22/11

1:31 p.m.-11:27 p.m.

1 stop8h 56m

C$ 415

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 cheapest month to fly to Chicago Midway Airport?

In general, March 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 March, then departing from Montreal during the month January is also very affordable. Most momondo users find prices during this month for around C$ 0.

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	C$ 228
Fastest flight time	4h 37m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Montreal in the past 72 hours is C$ 228. The best round-trip flight deal from Montreal to Chicago Midway Airport found on momondo in the last 72 hours is C$ 388.

The fastest flight from Montreal to Chicago Midway Airport takes 4h 37m

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 37m 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?
As of September 2026, 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 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?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Montreal to Chicago Midway Airport is Porter Airlines (100% of 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 C$ 242	Free Cancellation	Rating 8.0 458 reviews		Search Porter Airlines flights

Merrillville

Benton Harbor

Hammond

Munster

Valparaiso

Portage

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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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Cheap flights from Montreal to Chicago from C$ 228

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 14/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Montreal to Chicago

Cheap round-trip flights

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Cheap last-minute flights

Big names, great deals

Big names, great deals

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Filter for what you want

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Delta flights from Montreal to Chicago Midway Airport

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

Porter Airlines flights from Montreal to Chicago Midway Airport

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

momondo Fare Finder

Use the filters below to find and compare flights from Montreal to Chicago Midway Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Montreal to Chicago Midway Airport

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

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

When to book flights from Montreal to Chicago Midway Airport

Cheap Montreal to Chicago Midway Airport (YMQ to MDW) flight deals and tips

Best price found

Fastest flight time

Direct flights

Frequently asked questions about flying 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

Travelling to a place near Chicago?

Why use momondo?

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

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Popular flights according to clicks in the last 7 days on momondo

Montreal flight routes

According to popular flight searches on momondo this year

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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