YUL - MDW

C$ 232 Find Cheap Flights from Montreal to Chicago Midway Airport – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montreal to Chicago departing on 16/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 373
Typical prices: C$ 341-C$ 394
Porter Airlines
Sat 12/9Sat 19/9
YUL - MDW • 1 stop
Cheapest one-way flights
C$ 232
Porter Airlines
Wed 16/9
YUL - MDW • 1 stop
Top airlines
Cheapest • from C$ 373 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between Montreal and Chicago. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg C$ 502 (round-trip)
Shortest trip • 4h 34m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Montreal to Chicago (YUL-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montreal to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Montreal to Chicago

Sat, 12 Sep - Sat, 19 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 373Porter Airlines
Wed, 2 Sep - Tue, 8 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 373Porter Airlines
Thu, 20 Aug - Tue, 25 Aug
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:10 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 375Porter Airlines
Thu, 24 Sep - Tue, 29 Sep
Porter Airlines Logo
9:00 a.m. - 2:35 p.m.
YUL
-
MDW
6h 35m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 375Porter Airlines
Wed, 2 Sep - Tue, 8 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 376Porter Airlines
Wed, 2 Sep - Tue, 8 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 379Porter Airlines
Sat, 19 Sep - Sat, 26 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 379Porter Airlines
Wed, 9 Sep - Wed, 16 Sep
Porter Airlines Logo
9:00 a.m. - 2:35 p.m.
YUL
-
MDW
6h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 9:12 p.m.
MDW
-
YUL
4h 52m
1 stop
C$ 379Porter Airlines
Wed, 30 Sep - Sat, 3 Oct
Delta Logo
6:00 a.m. - 9:07 a.m.
YUL
-
MDW
4h 07m
1 stop
Delta Logo
6:40 p.m. - 11:27 p.m.
MDW
-
YUL
3h 47m
1 stop
C$ 394Delta
Wed, 30 Sep - Wed, 7 Oct
Delta Logo
6:00 a.m. - 9:07 a.m.
YUL
-
MDW
4h 07m
1 stop
Delta Logo
1:27 p.m. - 11:25 p.m.
MDW
-
YUL
8h 58m
1 stop
C$ 394Delta
Booking Insights

KAYAK's insights & trends for Montreal to Chicago flights

Get data-powered insights and trends into flights from Montreal to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport is January, where tickets cost C$ 0 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is C$ 883 and C$ 659 respectively.

Good to know

Low season

May

Cheapest flight

C$ 232
Best time to beat the crowds (49% less expensive on average)
Most popular time to fly (37% more expensive on average)
Flight from Montreal 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Montreal to Chicago Midway Airport flights

  • What is the cheapest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport was C$ 232 for a one-way ticket and C$ 373 for a round-trip.

  • Which aircraft models fly most regularly from Montreal to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Montreal to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Montreal to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Montreal to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Montreal is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Montreal to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Montreal with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Montreal to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Montreal up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Montreal to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Montreal to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Montreal to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 449 reviews
6.9Entertainment
7.5Food
8.0Comfort
8.6Crew
8.2Boarding
Airline reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

4.0 OkayJeff, Jul 2026
YYZ - SFO
Read more Porter Airlines reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

Organization and the adjusted times but the snacks could be of a bigger portion

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

All good the seats a little tight and no I pad screen

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

Everything you need to know for your flight from Montreal to Chicago

Information on your arrival and departure airports