What percentage of Montreal to Chicago flights are direct?

In the trailing 90 days, approximately 31.9% of flights from Montreal to Chicago were direct. For flights that include 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 at least one connection. Travelers should consider this when planning their journey.

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

The median direct flight time from Montreal to Chicago is 4 hours and 54 minutes. This route covers a distance of 1198 kilometers. For flights with one stop, the median travel time increases to 7 hours and 39 minutes. Travelers should factor in these durations when planning their itinerary, especially if considering connecting flights.

How often do Montreal to Chicago flight prices drop?

Historically, flight prices for the Montreal to Chicago route experience regular drops. This indicates that price fluctuations are a common occurrence for this particular route. Travelers may find opportunities to secure lower fares due to these frequent price adjustments. Monitoring prices consistently can be beneficial.

Flights From Montreal

To Chicago

Cheap Flights from Montreal to Chicago

Browse current best options from Montreal. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Montreal

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

Prices updated 7 days ago

482 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Montreal to Chicago

Explore current cheapest deals departing from Montreal to Chicago

2027-02-02 – 2027-02-05
YMQ - Chicago
74% AI deal score
CA$443
CA$335
Round trip
2027-04-06 – 2027-04-13
YMQ - Chicago
46% AI deal score
CA$305
CA$338
Round trip
2026-12-15 – 2027-01-01
YMQ - Chicago
45% AI deal score
CA$271
CA$341
Round trip
2027-01-13 – 2027-01-17
YMQ - Chicago
46% AI deal score
CA$312
CA$341
Round trip
2026-11-17 – 2026-11-24
YMQ - Chicago
69% AI deal score
CA$423
CA$342
Round trip
2026-12-09 – 2026-12-13
YMQ - Chicago
47% AI deal score
CA$329
CA$342
Round trip
2027-01-15 – 2027-01-18
YMQ - Chicago
47% AI deal score
CA$321
CA$342
Round trip
2027-01-23 – 2027-01-29
YMQ - Chicago
70% AI deal score
CA$457
CA$342
Round trip
2027-04-17 – 2027-04-19
YMQ - Chicago
46% AI deal score
CA$306
CA$342
Round trip
2026-12-11 – 2026-12-14
YMQ - Chicago
75% AI deal score
CA$492
CA$342
Round trip

Montreal to Chicago: Overview

Insights for flights from Montreal to Chicago

For those seeking cheap flights from Montreal to Chicago, December and February stand out as the most budget-friendly months, both with a median fare of $306. January also offers competitive pricing, with a median fare of $309. These months present the best opportunities for finding lower prices on this route.

Fares for flights from Montreal to Chicago typically range from $488–$876, with a median of $627. Right now, current fares are significantly below the typical level, and 32% of recent fares were classified as a good price. New deals show up several times a week, indicating a regular cadence of new offers for this route.

When flying from Montreal to Chicago, most itineraries connect at least once, with only 31.9% of recent fares being non-stop. For connecting flights, the typical number of stopovers is 2, which can significantly extend travel time.

A typical journey from Montreal to Chicago takes about 4h 54m, including connections. While the non-stop flight time is also 4h 54m, connecting itineraries have a median duration of 17h 44m, reflecting the impact of stopovers on overall travel time.

The distance between Montreal and Chicago is 1198 km, classifying this as a short-haul route. This distance means you can expect a relatively quick journey, especially if you find a direct flight.

How much is a round trip from Montreal to Chicago

Regular price: CA$355 - CA$533

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

The regular price range for flights from Montreal to Chicago is between 355 CAD and 533 CAD. The current lowest deal is 330 CAD with Porter Airlines, for travel from Feb 2-Feb 5.

now CA$330

Low CA$355

High CA$533

The cheapest time to fly from Montreal to Chicago

The cheapest month to fly from Montreal to Chicago is February, with a median price of $306. The most expensive month is August, with a median price of $674. Prices are generally lower from January to December.

February

Cheapest

Flights from CA$306

August

Most Expensive

Flights from CA$674

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Montreal to Chicago

Air Canada

Last-minute flights going from Montreal to Chicago

Tue, Oct 27

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (ORD)

Deutsche Luft Hansa

CA$1,010

CA$642

One-way

Tue, Oct 27

⌛ Last-Minute

YHU - Chicago

Montreal (YHU) - Chicago (ORD)

Porter Airlines

CA$957

CA$669

One-way

Wed, Oct 28

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Deutsche Luft Hansa

CA$1,680

CA$642

One-way

Thu, Oct 29

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Deutsche Luft Hansa

CA$1,638

CA$685

One-way

Fri, Oct 30

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Deutsche Luft Hansa

CA$1,642

CA$683

One-way

Thu, Nov 12

⌛ Last-Minute

YUL - Chicago

Montreal (YUL) - Chicago (MDW)

Deutsche Luft Hansa

CA$521

CA$429

One-way

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

3 nights

Oct 28 - Oct 31

CA$1,680 → CA$644

62%

2 nights

Oct 29 - Oct 31

CA$1,638 → CA$686

58%

2 nights

Dec 2 - Dec 4

CA$692 → CA$425

39%

3 nights

Dec 2 - Dec 5

CA$688 → CA$425

38%

Popular Airports to fly from Montreal to Chicago

Montreal - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares for flights from Montreal to Chicago are below the typical level.

📅 Best time to fly

Cheapest flights in December, February, and January

Historically, the cheapest flights from Montreal to Chicago are in December ($306), February ($306), and January ($309).

⏱️ Flight duration

Direct flights take 4h 54m

Direct flights from Montreal to Chicago typically take 4h 54m, while connecting flights average 17h 44m.

✈️ Airlines & availability

Connecting flights are more common

Historically, 31.9% of flights from Montreal to Chicago are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Air Canada offers direct flights

Air Canada is one airline that has historically offered direct flights on the Montreal to Chicago route.

🎯 Booking tip

Good prices are available 32% of the time

Historically, good prices for flights from Montreal to Chicago are available 32% of the time.

Montreal main airports to depart from

Montréal–Pierre Elliott Trudeau International (YUL)

Cheapest

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

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

💸 Flights from ~CA$393

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections to Chicago and beyond.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~CA$396

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

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

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

💸 Flights from ~CA$617

Business & First Class Flight Deals to Chicago

$610

Save $555

Porter Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from Montreal to Chicago 60+ days in advance typically yields the lowest average prices, around $348. Prices tend to increase as the departure date approaches. For instance, flights booked 28-59 days out average $590, while those booked within 0-6 days of departure average $781. Planning ahead can result in significant savings on this route.

Across the trailing quarter, a flight from Montreal to Chicago is considered cheap if it's priced at or below $488. The median price for this route was $627 during the same period. Prices can vary, with 75% of fares historically being $876 or less. Aiming for a price below the $488 threshold can help secure a good deal.

Historically, December and February have been the cheapest months to fly from Montreal to Chicago, both with a median price of $306. January also offers competitive prices, with a median of $309. These months are significantly more affordable than the annual median price of $627 for this route. Travelers looking for lower fares should consider these months.

Related routes

More routes from Montreal

Flights from Montreal to Cancún Flights from Montreal to Cleveland Flights from Montreal to Copenhagen Flights from Montreal to Dhaka Flights from Montreal to Dubai Flights from Montreal to Dublin Flights from Montreal to Faro Flights from Montreal to Fort Lauderdale Flights from Montreal to Fort Myers Flights from Montreal to Frankfurt Flights from Montreal to Kochi Flights from Montreal to New Delhi

Flights to Chicago from other cities

Flights from Accra to Chicago Flights from Addis Ababa to Chicago Flights from Albuquerque to Chicago Flights from Amman to Chicago Flights from Amsterdam to Chicago Flights from Anchorage to Chicago Flights from Athens to Chicago Flights from Atlanta to Chicago Flights from Auckland to Chicago Flights from Calgary to Chicago Flights from Toronto to Chicago Flights from Zürich to Chicago

Montreal to Chicago: Overview

Insights for flights from Montreal to Chicago

How much is a round trip from Montreal to Chicago

Regular price: CA$355 - CA$533

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

The regular price range for flights from Montreal to Chicago is between 355 CAD and 533 CAD. The current lowest deal is 330 CAD with Porter Airlines, for travel from Feb 2-Feb 5.

now CA$330

Low CA$355

High CA$533

The cheapest time to fly from Montreal to Chicago

February

Cheapest

Flights from CA$306

August

Most Expensive

Flights from CA$674

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec