What percentage of Montreal to Chicago flights are direct?

Across 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 indicates that while direct options are available, a significant portion of flights on this route involve connections.

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

A direct flight from Montreal to Chicago typically takes about 2 hours and 40 minutes, covering a distance of 1198 kilometers. Flights with one stop generally have a median duration of 6 hours and 18 minutes. This difference highlights the time savings associated with choosing a direct route.

How often do Montreal to Chicago flight prices drop?

Historically, flight prices for the Montreal to Chicago route have shown frequent drops. This suggests that travelers may often find opportunities for price reductions. Monitoring prices consistently can be beneficial for securing a more favorable fare.

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

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Montreal to Chicago

Explore current cheapest deals departing from Montreal to Chicago

2026-11-11 – 2026-11-13
YMQ - Chicago
46% AI deal score
CA$301
CA$335
Round trip
2026-11-24 – 2026-11-30
YMQ - Chicago
45% AI deal score
CA$294
CA$365
Round trip
2026-11-12 – 2026-11-17
YMQ - Chicago
45% AI deal score
CA$301
CA$365
Round trip
2026-11-03 – 2026-11-09
YMQ - Chicago
45% AI deal score
CA$278
CA$367
Round trip
2027-02-17 – 2027-02-21
YMQ - Chicago
68% AI deal score
CA$449
CA$369
Round trip
2026-11-03 – 2026-11-12
YMQ - Chicago
45% AI deal score
CA$264
CA$371
Round trip
2026-11-03 – 2026-11-05
YMQ - Chicago
45% AI deal score
CA$292
CA$371
Round trip
2026-11-03 – 2026-11-06
YMQ - Chicago
45% AI deal score
CA$290
CA$371
Round trip
2026-11-03 – 2026-11-07
YMQ - Chicago
45% AI deal score
CA$290
CA$371
Round trip
2026-11-03 – 2026-11-11
YMQ - Chicago
45% AI deal score
CA$267
CA$371
Round trip

Montreal to Chicago: Overview

Insights for flights from Montreal to Chicago

For travelers looking for cheap flights from Montreal to Chicago, December stands out as the most affordable month, with a median fare of $245. Other cost-effective options include April and May, where median fares are $284 and $287 respectively. Planning your trip around these months can lead to significant savings.

Fares for flights from Montreal to Chicago typically range from $313 to $674, with a median price of $475. Right now, current fares are above the typical level. Only 7% of recent fares were classified as a good price, indicating that finding a low fare may require some flexibility. New deals appear almost daily, so setting up a price alert can help you track fare changes.

When flying from Montreal to Chicago, most itineraries connect at least once. Only 36.5% of recent fares were for direct flights from Montreal to Chicago. For connecting itineraries, the typical number of connections is 2, which can extend travel time.

A typical journey from Montreal to Chicago, including connections, takes about 5h 54m. This duration accounts for the fact that most itineraries involve at least one stopover, making the total travel time longer than a direct flight would be. The median flight time is 354 minutes.

The distance between Montreal and Chicago is 1198 kilometers, classifying this as a short-haul route. This means you can expect a relatively brief journey, though connecting flights will naturally extend the overall travel duration.

How much is a round trip from Montreal to Chicago

Regular price: CA$250 - CA$526

Prices for flights from Montreal to Chicago are currently within the regular range.

The regular price range for flights from Montreal to Chicago is between 250 CAD and 526 CAD. The current lowest deal is 335 CAD with Air Canada for travel from Nov 11-Nov 13.

now CA$335

Low CA$250

High CA$526

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, Sep 24

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (ORD)

Air Canada

CA$521

CA$376

One-way

Sat, Sep 26

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (ORD)

Air Canada

CA$510

CA$379

One-way

Thu, Oct 1

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (ORD)

Air Canada

CA$463

CA$385

One-way

Thu, Oct 1

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,080

CA$397

One-way

Thu, Oct 1

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,166

CA$397

One-way

Thu, Oct 1

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Porter Airlines

CA$1,168

CA$399

One-way

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

2 nights

Oct 2 - Oct 4

CA$1,168 → CA$390

67%

3 nights

Oct 2 - Oct 5

CA$1,166 → CA$396

66%

2 nights

Oct 1 - Oct 3

CA$1,168 → CA$399

66%

4 nights

Oct 1 - Oct 5

CA$1,166 → CA$397

66%

Popular Airports to fly from Montreal to Chicago

Montreal - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares are above the typical level for this route, with a median price of $475.

📅 Best time to fly

Fly in December for the best prices

Historically, December, April, and May offer the lowest median prices for this route.

⏱️ Flight duration

Flights typically take 5h 54m

The median flight duration for this route is 5 hours and 54 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 63.5% of recent deals, with a median of 2 stopovers.

🏆 Airline highlight

Air Canada offers direct flights

Air Canada is one airline offering direct flights on this route.

🎯 Booking tip

Deals appear frequently

Deals for this route appear frequently, offering good opportunities to find savings.

Montreal main airports to depart from

Montréal–Pierre Elliott Trudeau International (YUL)

Cheapest

Fly from Montréal–Pierre Elliott Trudeau International for convenient connections to Chicago.

📍 ~14 km from Montreal city center (reachable by car or bus)

💸 Flights from ~CA$361

Montreal Saint-Hubert Longueuil (YHU)

Consider Montreal Saint-Hubert Longueuil for an alternative departure point to Chicago.

📍 ~12 km from Montreal city center (reachable by car or bus)

💸 Flights from ~CA$443

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Consider Chicago Midway International for flights to Chicago, offering a convenient arrival option for your trip.

📍 ~14 km from Chicago city center (reachable by car)

💸 Flights from ~CA$367

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers a significant carrier presence and direct flight options for Chicago travelers.

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

💸 Flights from ~CA$526

Business & First Class Flight Deals to Chicago

$539

Save $510

Porter Airlines

Business Class

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 generally sees an average price of $508. For those planning further ahead, flights booked 60+ days out had an average price of $493, while those booked 14-27 days in advance averaged $438.

Based on historical data from the trailing 90 days, a good price for a flight from Montreal to Chicago is considered to be around $313 or less. The median price for this route across the trailing quarter was $475. Prices tend to increase significantly, with 75% of fares being $674 or higher.

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 is typically around $475. While May is listed among the cheapest months, it also represents the most expensive month when considering the overall annual median.

Related routes

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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$250 - CA$526

Prices for flights from Montreal to Chicago are currently within the regular range.

The regular price range for flights from Montreal to Chicago is between 250 CAD and 526 CAD. The current lowest deal is 335 CAD with Air Canada for travel from Nov 11-Nov 13.

now CA$335

Low CA$250

High CA$526

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