YUL - MDW

C$ 256 Find Cheap Flights from Montreal to Chicago Midway Airport – Compare and Save

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Everything you should know

Cheapest round-trip
C$ 421
Typical prices: C$ 293-C$ 498
Delta
Mon 12/11Fri 16/11
YUL - MDW • 1 stop
Cheapest one-way flights
C$ 256
Typical prices: C$ 231-C$ 448
Delta
Tue 27/11
YUL - MDW • 1 stop
When to book
16 weeks
in advance
Our data shows that travellers 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 C$ 418 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 4h 58m (one-way)
Insights
Insights
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you enjoy your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Montreal to Chicago (YUL-MDW)

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

Recent round-trip flight deals from Montreal to Chicago

Thu, 12 Nov - Mon, 16 Nov
Delta Logo
12:50 p.m. - 6:04 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 14m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:05 p.m. - 11:48 p.m.MDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
9h 43m1 stop Atlanta Hartsfield-Jackson
C$ 421Delta
Thu, 3 Dec - Sun, 6 Dec
KLM Logo
6:00 a.m. - 9:37 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
KLM Logo
6:41 p.m. - 11:33 p.m.MDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
3h 52m1 stop Detroit Metropolitan Wayne County
C$ 452KLM
Thu, 12 Nov - Mon, 16 Nov
Delta Logo
6:00 a.m. - 9:46 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
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$ 455Delta
Fri, 13 Nov - Mon, 16 Nov
Delta Logo
6:00 a.m. - 12:51 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
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$ 455Delta
Thu, 19 Nov - Mon, 23 Nov
KLM Logo
6:00 a.m. - 9:46 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
KLM Logo
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$ 460KLM
Thu, 19 Nov - Mon, 23 Nov
KLM Logo
6:00 a.m. - 9:46 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
KLM Logo
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$ 462KLM
Thu, 19 Nov - Mon, 23 Nov
Delta Logo
12:50 p.m. - 6:04 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 14m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:29 p.m. - 11:30 p.m.MDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 01m1 stop Minneapolis St Paul
C$ 469Delta
Thu, 12 Nov - Fri, 13 Nov
Delta Logo
6:00 a.m. - 12:51 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
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$ 469Delta
Wed, 11 Nov - Thu, 12 Nov
Delta Logo
7:10 a.m. - 11:50 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 40m1 stop Minneapolis St Paul
Delta Logo
1:05 p.m. - 11:48 p.m.MDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
9h 43m1 stop Atlanta Hartsfield-Jackson
C$ 469Delta
Wed, 18 Nov - Mon, 23 Nov
Delta Logo
6:00 a.m. - 12:51 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
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$ 469Delta
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 C$ 293 to C$ 498. The lowest price found in the past 5 days was C$ 421, 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 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 C$ 208 round-trip.
•November (C$ 652) and September (C$ 593) 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

C$ 256
Beat the crowds with an average 65% drop in traveller numbers.
The most popular month to fly with an average 86% increase in traveller numbers.
One-way flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

When to book flights from Montreal to Chicago

Are your dates flexible? Find out the best times to travel from Montreal to Chicago 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.

  • Which 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 does a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport take?

    There are currently no direct 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 C$ 293 to C$ 498, with an average of C$ 403 over the past 12 months. Anything below C$ 293 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 C$ 403 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 C$ 421 to C$ 2,171. 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 C$ 298, which is 12% 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 C$ 117 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 C$ 285 round-trip on average, while Sunday is the most expensive at C$ 467, a difference of C$ 182.

    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 when travelling 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.

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

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, River North, and Grant Park. 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 C$ 285, about C$ 182 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 C$ 208 round-trip in that month – typically C$ 443 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 Chicago

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

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago