Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

YUL - MDW

$159 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 Midway departing on 2/15. 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
0 bags

Search 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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap Flight Deals from Montreal to Chicago Midway Airport (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 Midway Airport 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.

Recent round-trip flight deals from Montreal to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Montreal to Midway.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:50 am - 12:10 pmYUL-MDW
6h 20m1 stop
1:05 pm - 7:25 pmMDW-YUL
5h 20m1 stop
$262Porter Airlines
Find Deal
Fri, Feb 14 - Sun, Feb 16
6:50 am - 12:10 pmYUL-MDW
6h 20m1 stop
1:05 pm - 7:25 pmMDW-YUL
5h 20m1 stop
$273Porter Airlines
Find Deal
Fri, Jan 24 - Thu, Feb 13
6:50 am - 12:10 pmYUL-MDW
6h 20m1 stop
1:05 pm - 7:25 pmMDW-YUL
5h 20m1 stop
$285Porter Airlines
Find Deal
Fri, Jan 24 - Mon, Feb 3
6:50 am - 12:10 pmYUL-MDW
6h 20m1 stop
1:05 pm - 7:25 pmMDW-YUL
5h 20m1 stop
$286Porter Airlines
Find Deal
Fri, Jan 17 - Sun, Jan 19
8:55 am - 12:10 pmYUL-MDW
4h 15m1 stop
10:58 am - 12:40 amMDW-YUL
12h 42m2 stops
$371
Find Deal
Fri, Jan 17 - Sun, Jan 19
8:55 am - 12:10 pmYUL-MDW
4h 15m1 stop
10:58 am - 12:40 amMDW-YUL
12h 42m2 stops
$373
Find Deal
Thu, Jan 16 - Sun, Jan 19
2:50 pm - 10:20 pmYUL-MDW
8h 30m1 stop
3:41 pm - 11:52 pmMDW-YUL
7h 11m1 stop
$384Delta
Find Deal
Sat, Jan 18 - Sun, Jan 19
6:00 am - 5:43 pmYUL-MDW
12h 43m1 stop
1:26 pm - 11:40 pmMDW-YUL
9h 14m1 stop
$412WestJet
Find Deal
Fri, Feb 7 - Tue, Feb 11
7:30 am - 1:02 pmYUL-MDW
6h 32m1 stop
9:20 am - 11:18 pmMDW-YUL
12h 58m1 stop
$440WestJet
Find Deal
Thu, Jun 12 - Thu, Jun 26
6:00 am - 4:12 pmYUL-MDW
11h 12m2 stops
5:05 pm - 11:25 pmMDW-YUL
5h 20m1 stop
$529Delta
Find Deal
Sat, Jan 18 - Sun, Jan 19

Flights from Montreal to Midway - Travel Insights & Trends

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

What’s the cheapest day of the week to fly from Montreal to Chicago Midway Airport?

The average price of all round-trip flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Montreal to Chicago Midway Airport, you should consider leaving on a Monday and avoid Sundays if you are looking for the best rates. For your return to Montreal, you’ll find the best rates on Sundays and the most expensive ones on Mondays.

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 March, where tickets cost $263 (return) on average. On the other hand, the most expensive months are October and August, where the average cost of round-trip tickets is $462 and $437 respectively.

Good to know

Low season

April

High season

December

Cheapest flight

$159
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Montreal to Chicago Midway Airport

When to book flights from Montreal to Midway

Are your dates flexible? Find out the best times to travel from Montreal to Midway 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 $159 for a one-way ticket and $262 for a round-trip.

  • Do I need a passport to fly between Montreal and Chicago Midway Airport?

    A passport is required to fly from Montreal to Chicago Midway Airport.

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

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

  • Which airline alliances offer flights from Montreal to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Montreal and Chicago Midway Airport.

  • 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 travelers 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. Booking your flights between Montreal and MDW can sometimes prove cheaper using this method.

  • 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.

See more FAQs

Top airline flying from Montreal to Midway

 
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 Midway? 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.
7.9
Porter AirlinesOverall score based on 281 reviews
8.7Crew
6.9Entertainment
7.6Food
8.0Comfort
8.1Boarding
Airline reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

10.0 ExcellentJoan, Nov 2024YOW - YYZ
Read more Porter Airlines reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

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

Information on your arrival and departure airports

Midway (MDW)
Montreal (YUL)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.