Cheap flights from Montreal to Chicago Midway Airport

YMQ — MDW
1 Feb — 8 Feb1
Return
1 adult
Economy
From?
To?
Wed 1/2
Wed 8/2

How far in advance should I book a flight from Montreal to Chicago Midway Airport?

Users have found that booking a flight from Montreal to Chicago Midway Airport at least 60 days early can save you up to 88% on average compared to booking a flight this week. If booking 60 days before your flight isn’t an option for you, users have found flights from Montreal to Chicago Midway Airport for as little as C$ 587 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 853 for flights departing within the next 3 days.

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

Due to multiple factors, expect to potentially pay more when booking in April. For low rates, November can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Montreal in November are about C$ 450 on average during November, but can be found for as low as C$ 310.

When is the cheapest time to fly from Montreal to Chicago Midway Airport (YMQ - MDW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Montreal to Chicago Midway Airport as you normally would.

Cheap flights from Montreal to Midway in January, February 2023

The best prices found for YMQ to MDW flights for January, February
16 Feb. - 19 Feb.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 40m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 290

Porter Airlines

Deal found 25/1

23 Feb. - 3 Mar.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

4h 50m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 294

Porter Airlines

Deal found 26/1

25 Feb. - 4 Mar.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

4h 05m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 301

Porter Airlines

Deal found 24/1

Montreal to Midway 2023 flight deals

Cheap flights to Midway from Montreal found for this year
16 Feb. - 19 Feb.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 40m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 290

Porter Airlines

Deal found 25/1

23 Feb. - 3 Mar.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

4h 50m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 294

Porter Airlines

Deal found 26/1

17 Apr. - 20 Apr.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

4h 52m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 57m
C$ 297

Porter Airlines

Deal found 26/1

Cheap Porter Airlines flights from Montreal to Midway

16 Feb. - 19 Feb.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 40m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 290

Porter Airlines

Deal found 25/1

23 Feb. - 3 Mar.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

4h 50m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 294

Porter Airlines

Deal found 26/1

17 Apr. - 20 Apr.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

4h 52m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 57m
C$ 297

Porter Airlines

Deal found 26/1

Cheap Delta flights from Montreal to Midway

30 Mar. - 2 Apr.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 57m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 33m
C$ 378

Delta

Deal found 25/1

30 Mar. - 2 Apr.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 57m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 33m
C$ 405

Delta

Deal found 24/1

Last minute flights from Montreal to Midway

Late deals on round-trip flights to Midway from Montreal, departing today and this week
2 Feb. - 10 Feb.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 40m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

6h 03m
C$ 563

Porter Airlines

Deal found 25/1

2 Feb. - 4 Feb.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 30m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

5h 23m
C$ 568

Porter Airlines

Deal found 25/1

1 Feb. - 8 Feb.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

6h 40m
MDW

Chicago Midway

YUL

Montreal Pierre Elliott Trudeau Intl

1 stop

6h 03m
C$ 635

Porter Airlines

Deal found 25/1

One-way flights to Midway from Montreal

The cheapest one-way flights from Montreal to Midway
13 Mar.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

5h 05m
C$ 172

Porter Airlines

Deal found 25/1

16 Feb.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

4h 20m
C$ 174

Porter Airlines

Deal found 25/1

5 Mar.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

5h 15m
C$ 175

Porter Airlines

Deal found 25/1

Related info for your journey

Useful info, stats and facts about Montreal to Midway flights.

Which airlines flying from Montreal to Chicago Midway have flexible changes due to COVID-19?

Porter Airlines is one of the carriers that may have flexible change policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Montreal to Chicago Midway Airport for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Montreal to Chicago Midway Airport for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 290, but on average you can expect to pay C$ 328.

Are there last-minute flights available from Montreal to Chicago Midway Airport for under C$ 600?

There are currently 3+ open flights from Montreal to Chicago Midway Airport within the next 7 days for less than C$ 600.

What are the cheapest airlines flying from Montreal to Chicago Midway Airport round-trip?

Porter Airlines, at C$ 290, was found to be the cheapest airline from Montreal to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. You may be able to fly from Montreal to Chicago Midway Airport for 38% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Montreal to Chicago Midway Airport one-way?

One-way options have recently been found by users for as low as C$ 172 on Porter Airlines. Other airlines that offer cheap prices include Delta from C$ 369 and WestJet from C$ 481 one-way.

What are the cheapest flights from Montreal to Chicago Midway Airport?

While on average a flight from Montreal to Chicago Midway Airport is generally C$ 540, our data shows the cheapest flight currently is C$ 380. When looking at the most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago Midway), you can expect to pay C$ 294 for that flight.

Top airline flying from Montreal to Midway

The chart below displays the airlines Cheapflights users travelling from Montreal to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Porter AirlinesCheapestC$ 273AverageC$ 373FlexibilityNo cancel feeOn-time52%COVID-19 safety
Search Porter Airlines flights
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