YUL - MDW

$183 Find Cheap Flights from Montreal to Chicago Midway Airport - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$301
Typical prices: $209-$356
Delta
Mon 11/12Fri 11/16
YUL - MDW • 1 stop
Cheapest one-way
$183
Typical prices: $165-$320
Delta
Tue 11/27
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 57% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 48% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Toronto Island (YTZ)
Cheapest • Avg $299 (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

Thu, Nov 12 - Mon, Nov 16
Delta Logo
12:50 pm - 6:04 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 14m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:05 pm - 11:48 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
9h 43m1 stop Atlanta Hartsfield-Jackson
$301Delta
Thu, Dec 3 - Sun, Dec 6
KLM Logo
6:00 am - 9:37 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
KLM Logo
6:41 pm - 11:33 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
3h 52m1 stop Detroit Metropolitan Wayne County
$323KLM
Thu, Nov 12 - Mon, Nov 16
Delta Logo
6:00 am - 9:46 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:31 pm - 11:27 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
8h 56m1 stop Detroit Metropolitan Wayne County
$325Delta
Fri, Nov 13 - Mon, Nov 16
Delta Logo
6:00 am - 12:51 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:31 pm - 11:27 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
8h 56m1 stop Detroit Metropolitan Wayne County
$325Delta
Thu, Nov 19 - Mon, Nov 23
KLM Logo
6:00 am - 9:46 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
KLM Logo
1:31 pm - 11:27 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
8h 56m1 stop Detroit Metropolitan Wayne County
$329KLM
Thu, Nov 19 - Mon, Nov 23
KLM Logo
6:00 am - 9:46 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
KLM Logo
1:31 pm - 11:27 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
8h 56m1 stop Detroit Metropolitan Wayne County
$330KLM
Thu, Nov 12 - Fri, Nov 13
Delta Logo
6:00 am - 12:51 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:31 pm - 11:27 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
8h 56m1 stop Detroit Metropolitan Wayne County
$335Delta
Wed, Nov 11 - Thu, Nov 12
Delta Logo
7:10 am - 11:50 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 40m1 stop Minneapolis St Paul
Delta Logo
1:05 pm - 11:48 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
9h 43m1 stop Atlanta Hartsfield-Jackson
$335Delta
Wed, Nov 18 - Mon, Nov 23
Delta Logo
6:00 am - 12:51 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:31 pm - 11:27 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
8h 56m1 stop Detroit Metropolitan Wayne County
$335Delta
Thu, Nov 19 - Mon, Nov 23
Delta Logo
12:50 pm - 6:04 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 14m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:29 pm - 11:30 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 01m1 stop Minneapolis St Paul
$335Delta
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 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 typically range from $209 to $356. The lowest price found in the past 5 days was $301, on Delta.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport. It’s 30% cheaper than the average day, while Sunday is the most expensive, with prices 15% higher.

What’s 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 ($466) and September ($424) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 212% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights 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 57% 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

September

Cheapest flight

$183
Beat the crowds with an average 65% drop in travelers.
The most popular month to fly with an average 86% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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.

  • 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 41m 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.

  • 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 $209 to $356, with an average of $288 over the past 12 months. Anything below $209 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 55% above the $288 route average. Book 16 weeks before departure for the lowest fares.

  • 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 $301 to $1,552. That means the highest observed fare was about 5x 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 higher than usual. Average one-way flight prices are about $202, which is 6% above the typical average for this route.

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

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • 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).

  • 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) - 96% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 4% of one-stop connections

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

    Yes. Flexible dates can save you up to 39% on flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport. Saturday is the cheapest departure day at $204 round-trip on average, while Sunday is the most expensive at $334, a difference of $130.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • 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 41m, 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 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 Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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 are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $204, about $130 less than Sunday fares (39% 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 57% 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 $317 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 Chicago Midway Airport

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