What percentage of Montreal to Chicago flights are direct?

In the trailing 90 days, approximately 36.5% of flights from Montreal to Chicago were direct. For flights that included stopovers, the median number of stopovers was 2. This suggests that while direct options are available, a notable portion of routes involve connections.

How long does it take to fly from Montreal to Chicago?

A direct flight from Montreal to Chicago typically takes 2 hours and 40 minutes, covering a distance of 1198 kilometers. Flights with one stop, however, historically have a median duration of 6 hours and 18 minutes. This difference highlights the convenience of direct routes for this journey.

How often do Montreal to Chicago flight prices drop?

Historically, flight prices for the Montreal to Chicago route have shown frequent drops. This indicates that travelers may often find opportunities for lower fares. Monitoring prices over time can be beneficial for securing a more economical flight.

Flights From Montreal

To Chicago

Cheap Flights from Montreal to Chicago

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Deals from

Montreal

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 2 days ago

405 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Montreal to Chicago

Explore current cheapest deals departing from Montreal to Chicago

2026-08-11 – 2026-08-18
YMQ - Chicago
86% AI deal score
CA$1,217
CA$334
Round trip
2027-01-16 – 2027-01-20
YMQ - Chicago
79% AI deal score
CA$553
CA$334
Round trip
2026-09-03 – 2026-09-07
YMQ - Chicago
80% AI deal score
CA$566
CA$338
Round trip
2026-08-10 – 2026-08-12
YMQ - Chicago
86% AI deal score
CA$1,295
CA$342
Round trip
2026-09-07 – 2026-09-13
YMQ - Chicago
67% AI deal score
CA$418
CA$345
Round trip
2026-09-16 – 2026-09-20
YMQ - Chicago
68% AI deal score
CA$445
CA$346
Round trip
2027-01-06 – 2027-01-07
YMQ - Chicago
77% AI deal score
CA$539
CA$346
Round trip
2026-10-13 – 2026-10-17
YMQ - Chicago
84% AI deal score
CA$1,150
CA$351
Round trip
2026-08-14 – 2026-08-17
YMQ - Chicago
85% AI deal score
CA$1,270
CA$352
Round trip
2026-10-06 – 2026-10-13
YMQ - Chicago
84% AI deal score
CA$1,120
CA$352
Round trip

Montreal to Chicago: Overview

Insights for flights from Montreal to Chicago

For travelers seeking cheap flights from Montreal to Chicago, December stands out as the most economical month, with a median fare of just $245. Other favorable months include April, where the median fare is $284, and May, with a median fare of $287. Planning your trip during these months can lead to significant savings.

Fares for flights from Montreal to Chicago typically range from $313–$674, with a median fare of $475. Right now, current fares are above the typical level for this route. Only 7% of recent fares were classified as a good price, indicating that finding a particularly low fare may require some flexibility.

When flying from Montreal to Chicago, most itineraries connect at least once, as only 36.5% of recent fares were for direct flights from Montreal to Chicago. For connecting itineraries, the typical number of stopovers is 2. New deals appear almost daily, so setting up a price alert can help you track fare changes.

A typical journey from Montreal to Chicago takes approximately 5h 54m, including connections. This duration accounts for the fact that most itineraries involve at least one stopover. The distance covered on this route is 1198 kilometers, classifying it as a short-haul flight.

How much is a round trip from Montreal to Chicago

Regular price: CA$441 - CA$645

Prices are currently below the regular range.

The regular price range for flights from Montreal to Chicago is CAD 441 to CAD 645. The current lowest deal is CAD 366 with Porter Airlines, for travel from Sep 19-Sep 26.

now CA$366

Low CA$441

High CA$645

The cheapest time to fly from Montreal to Chicago

The cheapest month to fly from Montreal to Chicago is December, with a median price of $245. The most expensive month is July, with a median price of $545. Prices are generally lower from February to December.

December

Cheapest

Flights from CA$245

July

Most Expensive

Flights from CA$545

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Montreal to Chicago

Air Canada

Last-minute flights going from Montreal to Chicago

Thu, Aug 6

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,316

CA$414

One-way

Thu, Aug 6

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,363

CA$417

One-way

Thu, Aug 6

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,468

CA$444

One-way

Fri, Aug 7

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,344

CA$396

One-way

Fri, Aug 7

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,172

CA$400

One-way

Fri, Aug 7

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,428

CA$430

One-way

Biggest price drops on these dates for flights from Montreal to Chicago

3 nights

Aug 6 - Aug 9

CA$1,468 → CA$444

70%

3 nights

Aug 7 - Aug 10

CA$1,437 → CA$437

70%

4 nights

Aug 7 - Aug 11

CA$1,428 → CA$430

70%

1 night

Aug 11 - Aug 12

CA$1,343 → CA$378

72%

Popular Airports to fly from Montreal to Chicago

Montreal - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Montreal to Chicago are above the typical level, with 7% good prices historically.

📅 Best time to fly

Fly in December for the best prices

Historically, December is the cheapest month to fly from Montreal to Chicago, with median prices around $245.

⏱️ Flight duration

Expect a 5h 54m flight duration

Flights from Montreal to Chicago typically take 5h 54m, covering a distance of 1198 km.

✈️ Airlines & availability

Connecting flights are dominant

Only 36.5% of recent flights from Montreal to Chicago are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Porter Airlines offers a deal at $366

Porter Airlines has a deal from Montreal to Chicago for $366, departing September 19 and returning September 26.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Montreal to Chicago are frequent, appearing within a 30-day window.

Montreal main airports to depart from

Montréal–Pierre Elliott Trudeau International (YUL)

Cheapest

Montréal–Pierre Elliott Trudeau International Airport (YUL) is a convenient option for flights from Montreal to Chicago.

📍 ~15 km from Montreal city center (reachable by car or bus).

💸 Flights from ~$236

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering many connections from Montreal.

📍 ~20 km from Chicago city center (reachable by car, train, and bus)

💸 Flights from ~$236

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

Milwaukee offers significant carrier presence and direct flight options, easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~CA$513

Business & First Class Flight Deals to Chicago

83% AI deal score

$942

$446

Save $496

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Montreal to Chicago is typically 7-13 days before departure. During this period, the average price observed was $385. Booking within 0-6 days of departure typically sees an average price of $508. For those planning further ahead, prices averaged $496 for bookings made 28-59 days out, and $493 for bookings made 60+ days in advance.

Across the trailing quarter, a good price for a flight from Montreal to Chicago was considered to be $313 or less. The median price for this route was $475. Prices historically reached up to $674 for the more expensive fares in the trailing 90 days.

Historically, December has been the cheapest month to fly from Montreal to Chicago, with a median price of $245. April and May also offered competitive prices, with median fares of $284 and $287 respectively. The annual median price for this route was $475, indicating that these months represent significant savings.

Related routes

More routes from Montreal

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Flights to Chicago from other cities

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Montreal to Chicago: Overview

Insights for flights from Montreal to Chicago

How much is a round trip from Montreal to Chicago

Regular price: CA$441 - CA$645

Prices are currently below the regular range.

The regular price range for flights from Montreal to Chicago is CAD 441 to CAD 645. The current lowest deal is CAD 366 with Porter Airlines, for travel from Sep 19-Sep 26.

now CA$366

Low CA$441

High CA$645

The cheapest time to fly from Montreal to Chicago

December

Cheapest

Flights from CA$245

July

Most Expensive

Flights from CA$545

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec