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

WestJet, Delta, and KLM 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 October 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$ 259 Cheap Flights from Montreal to Chicago Midway Airport in 2026/27

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.

6:00 a.m. - 9:37 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

1:41 p.m. - 11:33 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

8h 52m1 stop Detroit Metropolitan Wayne County

C$ 420Delta

Thu, 3 Dec - Thu, 10 Dec

12:42 p.m. - 10:22 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

10h 40m1 stop Atlanta Hartsfield-Jackson

12:30 p.m. - 11:35 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

10h 05m1 stop Minneapolis St Paul

C$ 422Delta

Sat, 19 Dec - Mon, 4 Jan

12:50 p.m. - 6:04 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 14m1 stop Detroit Metropolitan Wayne County

6:44 p.m. - 11:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 43m1 stop Detroit Metropolitan Wayne County

C$ 433Delta

Tue, 10 Nov - Mon, 16 Nov

6:00 a.m. - 12:33 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

7h 33m1 stop Detroit Metropolitan Wayne County

5:59 p.m. - 11:10 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 11m1 stop Detroit Metropolitan Wayne County

C$ 439Delta

Thu, 1 Apr - Fri, 2 Apr

6:00 a.m. - 11:25 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

6:00 a.m. - 5:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

10h 27m1 stop Atlanta Hartsfield-Jackson

C$ 451Delta

Thu, 26 Nov - Sun, 29 Nov

6:00 a.m. - 9:46 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 46m1 stop Detroit Metropolitan Wayne County

9:30 a.m. - 3:58 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 28m1 stop Detroit Metropolitan Wayne County

C$ 451Delta

Wed, 11 Nov - Sat, 14 Nov

6:00 a.m. - 9:46 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 46m1 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$ 451Delta

Fri, 13 Nov - Tue, 17 Nov

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

7h 51m1 stop Detroit Metropolitan Wayne County

6:44 p.m. - 11:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 43m1 stop Detroit Metropolitan Wayne County

C$ 451Delta

Tue, 10 Nov - Mon, 16 Nov

7:10 a.m. - 4:39 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

10h 29m1 stop Minneapolis St Paul

9:30 a.m. - 3:58 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 28m1 stop Detroit Metropolitan Wayne County

C$ 451Delta

Tue, 10 Nov - Sat, 14 Nov

6:00 a.m. - 9:46 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 46m1 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$ 451Delta

Wed, 11 Nov - Mon, 16 Nov

Cheap last-minute flights

Enter your travel dates to find the best prices.

2:46 p.m. - 10:33 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

8h 47m1 stop Atlanta Hartsfield-Jackson

6:44 p.m. - 11:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 43m1 stop Detroit Metropolitan Wayne County

C$ 672Delta

Sat, 24 Oct - Mon, 9 Nov

7:00 a.m. - 4:14 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

10h 14m1 stop Atlanta Hartsfield-Jackson

6:44 p.m. - 11:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 43m1 stop Detroit Metropolitan Wayne County

C$ 672Delta

Fri, 23 Oct - Mon, 9 Nov

6:00 a.m. - 9:32 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 32m1 stop Detroit Metropolitan Wayne County

6:44 p.m. - 11:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 43m1 stop Detroit Metropolitan Wayne County

C$ 672Delta

Thu, 22 Oct - Mon, 9 Nov

6:00 a.m. - 9:32 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 32m1 stop Detroit Metropolitan Wayne County

5:13 p.m. - 11:48 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 35m1 stop Atlanta Hartsfield-Jackson

C$ 672Delta

Thu, 22 Oct - Tue, 10 Nov

6:00 a.m. - 9:32 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 32m1 stop Detroit Metropolitan Wayne County

9:29 a.m. - 4:15 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 46m1 stop Detroit Metropolitan Wayne County

C$ 672Delta

Thu, 22 Oct - Sun, 8 Nov

6:00 a.m. - 9:32 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 32m1 stop Detroit Metropolitan Wayne County

5:31 p.m. - 11:22 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 51m1 stop Minneapolis St Paul

C$ 715Delta

Thu, 22 Oct - Wed, 4 Nov

6:00 a.m. - 9:32 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 32m1 stop Detroit Metropolitan Wayne County

5:31 p.m. - 11:22 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

4h 51m1 stop Minneapolis St Paul

C$ 715Delta

Thu, 22 Oct - Sat, 7 Nov

7:00 a.m. - 4:14 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

10h 14m1 stop Atlanta Hartsfield-Jackson

9:29 a.m. - 4:15 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 46m1 stop Detroit Metropolitan Wayne County

C$ 732Delta

Thu, 22 Oct - Sun, 8 Nov

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$ 758Porter Airlines

Thu, 22 Oct - Sat, 24 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$ 760Porter Airlines

Thu, 22 Oct - Sat, 24 Oct

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KLM flights from Montreal to Chicago Midway Airport

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

KLM

8 Nov

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

7h 47m

1 stop

MDW12:47 p.m.Chicago Midway

11 Nov

MDW1:31 p.m.Chicago Midway

8h 56m

1 stop

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

C$ 458

KLM

14 Nov

YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl

9h 12m

1 stop

MDW3:12 p.m.Chicago Midway

15 Nov

MDW9:30 a.m.Chicago Midway

5h 28m

1 stop

YUL3:58 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 476

KLM

11 Nov

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

4h 46m

1 stop

MDW9:46 a.m.Chicago Midway

18 Nov

MDW1:31 p.m.Chicago Midway

8h 56m

1 stop

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

C$ 478

Delta flights from Montreal to Chicago Midway Airport

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

Delta

3 Dec

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

4h 37m

1 stop

MDW9:37 a.m.Chicago Midway

10 Dec

MDW1:41 p.m.Chicago Midway

8h 52m

1 stop

YUL11:33 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 420

Delta

19 Dec

YUL12:42 p.m.Montreal Pierre Elliott Trudeau Intl

10h 40m

1 stop

MDW10:22 p.m.Chicago Midway

4 Jan

MDW12:30 p.m.Chicago Midway

10h 05m

1 stop

YUL11:35 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 422

Delta

10 Nov

YUL12:50 p.m.Montreal Pierre Elliott Trudeau Intl

6h 14m

1 stop

MDW6:04 p.m.Chicago Midway

16 Nov

MDW6:44 p.m.Chicago Midway

3h 43m

1 stop

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

C$ 433

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

Thu 3/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Thu 10/12

1:41 p.m.-11:33 p.m.

1 stop8h 52m

C$ 420

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 19/12

12:42 p.m.-10:22 p.m.

1 stop10h 40m

Chicago Midway

Mon 4/1

12:30 p.m.-11:35 p.m.

1 stop10h 05m

C$ 422

Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 10/11

12:50 p.m.-6:04 p.m.

1 stop6h 14m

Chicago Midway

Mon 16/11

6:44 p.m.-11:27 p.m.

1 stop3h 43m

C$ 433

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 1/4

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

1 stop7h 33m

Chicago Midway

Fri 2/4

5:59 p.m.-11:10 p.m.

1 stop4h 11m

C$ 439

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/11

6:00 a.m.-11:25 a.m.

1 stop6h 25m

Chicago Midway

Sun 29/11

6:00 a.m.-5:27 p.m.

1 stop10h 27m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 11/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Sat 14/11

9:30 a.m.-3:58 p.m.

1 stop5h 28m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 13/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Tue 17/11

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

1 stop8h 56m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 10/11

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

1 stop7h 51m

Chicago Midway

Mon 16/11

6:44 p.m.-11:27 p.m.

1 stop3h 43m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 10/11

7:10 a.m.-4:39 p.m.

1 stop10h 29m

Chicago Midway

Sat 14/11

9:30 a.m.-3:58 p.m.

1 stop5h 28m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 11/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Mon 16/11

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

1 stop8h 56m

C$ 451

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$ 259
Fastest flight time	4h 46m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Montreal in the past 72 hours is C$ 259. The best round-trip flight deal from Montreal to Chicago Midway Airport found on momondo in the last 72 hours is C$ 420.

The fastest flight from Montreal to Chicago Midway Airport takes 4h 46m

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 46m 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 October 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$ 246	Free Cancellation	Rating 8.0 467 reviews		Search Porter Airlines flights

Merrillville

Benton Harbor

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

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Cheap flights from Montreal to Chicago from C$ 259

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 14/12. 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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Big names, great deals

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KLM flights from Montreal to Chicago Midway Airport

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

Delta flights from Montreal to Chicago Midway Airport

Our best Delta 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

Popular Cities in the United States

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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