YUL - MDW

$173 Find Cheap Flights from Montreal to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$281
Typical prices: $217-$355
Porter Airlines
Sun 10/14Wed 10/17
YUL - MDW • 1 stop
Cheapest one-way
$173
Typical prices: $160-$344
Porter Airlines
Thu 10/11
YUL - MDW • 1 stop
When to book
16 weeks
in advance
Our data shows that travelers who book at least 16 weeks in advance save around 56% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 48% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Toronto Island (YTZ)
Cheapest • Avg $303 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 4h 58m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Montreal to Midway (YUL-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Montreal to Midway

Wed, Oct 14 - Sat, Oct 17
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$281Porter Airlines
Wed, Oct 7 - Wed, Oct 14
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$282Porter Airlines
Fri, Oct 2 - Sun, Oct 4
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$282Porter Airlines
Thu, Oct 22 - Fri, Oct 23
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$282Porter Airlines
Sun, Oct 11 - Fri, Oct 16
Porter Airlines Logo
10:35 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 00m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$284Porter Airlines
Fri, Sep 25 - Mon, Sep 28
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$284Porter Airlines
Mon, Oct 19 - Wed, Oct 21
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$284Porter Airlines
Tue, Oct 20 - Wed, Oct 21
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$284Porter Airlines
Fri, Oct 2 - Tue, Oct 6
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$284Porter Airlines
Thu, Oct 1 - Sun, Oct 4
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$284Porter Airlines
Booking Insights

Price, demand and travel trends for Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport with more confidence.

How much is a round-trip flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

Round-trip flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport start at $281. Prices are typical for this route right now, with typical round-trip fares ranging from $217 to $355. The lowest price found in the past 5 days was $281 on Porter Airlines.

What's the cheapest day of the week to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

Monday is the cheapest day of the week to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport, it is 5% cheaper than the average day. Sunday is the most expensive day with flight prices 17% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

  • February is the cheapest month to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport at $149 round-trip.
  • November ($448) and August ($391) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 200% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport the cheapest?

Flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport are cheapest 16 weeks before departure. Booking in this window typically costs about 56% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flights

Low season

February

Cheapest flight

$173
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

When to book flights from Montreal to Midway

Are your dates flexible? Find out the best times to travel from Montreal to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport usually depart from Montreal Pierre Elliott Trudeau Intl (YUL) and arrive at Chicago Midway (MDW).

  • What cabin classes can I book on flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Only Economy Class is available on flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport.

  • Which airports do connecting flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport pass through?

    Connecting flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport most commonly pass through:

    • Toronto Island (YTZ) - 97% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 3% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

  • Can I save money by using flexible dates for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Yes. Being flexible with your travel dates can save you up to 19% on the Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport route. Monday is the cheapest departure day at $273 round-trip on average, while Sunday is the most expensive at $334, a difference of $61. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • How expensive are last-minute Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 55% above the route average of $285. Book 16 weeks before departure for the lowest fares.

  • How long is a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    There are currently no nonstop flights available from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport. Flights with 1 layover take between 4h 38m and 4h 58m in total, depending on the connection.

  • Do I need a passport to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $281 to $1,629. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport looking right now?

    One-way fares from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $178, which is 6% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Flying via Toronto Island (YTZ) gives the shortest average 1-stop total travel time at 4h 38m, compared with 4h 58m via Detroit Metropolitan Wayne County (DTW).

  • What is the time difference between Montreal Pierre Elliott Trudeau Intl Airport and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Montreal Pierre Elliott Trudeau Intl Airport (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • How much should I expect to pay for a Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flight?

    Round-trip flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport range from $217 to $355, with an average of $285 over the past 12 months. Anything below $217 counts as a good deal.

Your guide to booking Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Monday departure instead of Sunday. On this route, Monday flights average $273 - about $61 less than Sunday (18% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 16 weeks before you fly. On this route, that window historically saves about 56% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport trip for February. Fares historically average $149 round-trip in that month - typically $299 less than the most expensive month, which is November (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

More options for your flight from Montreal to Midway

Complete your trip to Midway with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago