YUL - MDW

C$ 165 Find Cheap Flights from Montreal to Chicago Midway Airport

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 1/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montreal to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montreal to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 222
Porter Airlines
Fri 8/5Sun 10/5
YUL - MDW • 1 stop
Cheapest one-way flights
C$ 165
Porter Airlines
Fri 1/5
YUL - MDW • 1 stop
Top airlines
Cheapest • from C$ 222 (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$ 421 (round-trip)
Shortest trip • 4h 48m (one-way)
Insights
Insights
Insights
Insights
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We hope you love your trip to Chicago!
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

Fri, 8 May - Sun, 10 May
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:15 p.m.
MDW
-
YUL
6h 50m
1 stop
C$ 222Porter Airlines
Fri, 8 May - Sun, 10 May
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 252Porter Airlines
Thu, 28 May - Sun, 31 May
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 258Porter Airlines
Fri, 1 May - Mon, 4 May
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 259Porter Airlines
Fri, 1 May - Mon, 4 May
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 261Porter Airlines
Fri, 5 Jun - Sun, 7 Jun
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 265Porter Airlines
Wed, 20 May - Tue, 26 May
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 269Porter Airlines
Wed, 27 May - Tue, 2 Jun
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 270Porter Airlines
Thu, 23 Apr - Mon, 27 Apr
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 272Porter Airlines
Thu, 16 Apr - Mon, 20 Apr
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 273Porter Airlines
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.

Which airlines provide the cheapest flights from Montreal to Chicago Midway Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Montreal to Chicago Midway Airport were found on Porter Airlines (C$ 222) and Delta (C$ 324).

Good to know

Low seasonSeptember
Cheapest flightC$ 165
Best time to beat the crowds (54% less expensive on average)
Most popular time to fly (15% 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 3 days, the lowest price for a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport was C$ 165 for a one-way ticket and C$ 222 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 424 reviews
8.0Comfort
8.6Crew
7.0Entertainment
7.6Food
8.2Boarding
Airline reviews

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

10.0 ExcellentDeanna, Mar 2026
YWG - YOW
Read more Porter Airlines reviews

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

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.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

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

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

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

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

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

Information on your arrival and departure airports