Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

YUL - MDW

$138 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 9/6. 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
Thu 6/27
Thu 7/4

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 42,816,550 times on KAYAK, and here is why:

Save 21% 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 Midway (YUL-MDW)

 
These are the cheapest deals for flights from Montreal to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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.

Recent one-way flight deals from Montreal to Midway

Only flying one-way? Below are some of the best one-way flight deals from Montreal to Midway found on KAYAK recently.

Recent last minute flight deals from Montreal to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Montreal to Midway.

Recent direct flight deals from Montreal to Midway

The latest deals for direct flights from Montreal to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Montreal to Midway

Find recent round-trip train or bus tickets from Montreal to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:45 am - 4:17 pmYUL-MDW
6h 32m1 stop
11:05 am - 6:00 pmMDW-YUL
5h 55m1 stop
$233Porter Airlines
Find Deal
Thu, Sep 5 - Tue, Sep 10
10:45 am - 4:17 pmYUL-MDW
6h 32m1 stop
8:00 am - 2:35 pmMDW-YUL
5h 35m1 stop
$234Porter Airlines
Find Deal
Tue, Sep 24 - Sat, Sep 28
3:10 pm - 7:02 pmYUL-MDW
4h 52m1 stop
8:00 am - 1:45 pmMDW-YUL
4h 45m1 stop
$235Porter Airlines
Find Deal
Sat, Jun 29 - Mon, Jul 29
3:10 pm - 7:02 pmYUL-MDW
4h 52m1 stop
8:00 am - 1:45 pmMDW-YUL
4h 45m1 stop
$236Porter Airlines
Find Deal
Sat, Jun 29 - Mon, Jul 1
12:47 pm - 5:04 pmYUL-MDW
5h 17m1 stop
5:45 pm - 11:01 pmMDW-YUL
4h 16m1 stop
$280Delta
Find Deal
Sun, Sep 1 - Sat, Sep 7
12:47 pm - 5:04 pmYUL-MDW
5h 17m1 stop
12:09 pm - 11:14 pmMDW-YUL
10h 05m1 stop
$310Delta
Find Deal
Tue, Jul 23 - Sat, Aug 3
7:30 am - 6:38 pmYUL-MDW
12h 08m1 stop
7:20 pm - 11:10 pmMDW-YUL
26h 50m1 stop
$326WestJet
Find Deal
Fri, Aug 30 - Wed, Sep 4
5:55 pm - 11:44 amYUL-MDW
18h 49m2 stops
10:28 am - 5:51 pmMDW-YUL
6h 23m1 stop
$339WestJet
Find Deal
Fri, Aug 9 - Tue, Aug 13
8:35 am - 8:08 pmYUL-MDW
12h 33m2 stops
5:15 pm - 10:50 pmMDW-YUL
4h 35m1 stop
$344
Find Deal
Sat, Aug 17 - Wed, Aug 21
4:45 pm - 9:37 pmYUL-MDW
5h 52m1 stop
9:07 pm - 10:11 amMDW-YUL
12h 04m2 stops
$373
Find Deal
Mon, Jul 8 - Fri, Jul 12
12:50 pm - 4:17 pmYUL-MDW
4h 27m1 stop
$138Porter Airlines
Find Deal
Fri, Sep 6
4:45 pm - 9:37 pmYUL-MDW
5h 52m1 stop
$144Porter Airlines
Find Deal
Mon, Sep 9
8:35 am - 11:32 amYUL-MDW
3h 57m1 stop
$145Porter Airlines
Find Deal
Sat, Jun 15
6:35 pm - 9:37 pmYUL-MDW
4h 02m1 stop
$146Porter Airlines
Find Deal
Tue, Jul 2
12:45 pm - 9:46 pmYUL-MDW
10h 01m1 stop
$170Delta
Find Deal
Sun, Sep 1
7:30 am - 6:38 pmYUL-MDW
12h 08m1 stop
$178WestJet
Find Deal
Sat, Aug 31
1:05 pm - 7:31 amYUL-MDW
19h 26m1 stop
$189
Find Deal
Sun, Jun 9
6:00 am - 12:42 pmYUL-MDW
7h 42m1 stop
$191Delta
Find Deal
Sun, Aug 11
9:15 pm - 11:44 amYUL-MDW
15h 29m2 stops
$201WestJet
Find Deal
Mon, Aug 26
1:05 pm - 7:31 amYUL-MDW
19h 26m1 stop
$215
Find Deal
Thu, Jun 6
10:40 am - 4:17 pmYUL-MDW
6h 37m1 stop
12:15 pm - 5:55 pmMDW-YUL
4h 40m1 stop
$360Porter Airlines
Find Deal
Sun, Jun 2 - Sun, Jun 9
6:35 pm - 9:37 pmYUL-MDW
4h 02m1 stop
5:25 pm - 10:30 pmMDW-YUL
4h 05m1 stop
$433Porter Airlines
Find Deal
Sun, Jun 2 - Sun, Jun 9
6:35 pm - 9:37 pmYUL-MDW
4h 02m1 stop
5:15 pm - 10:50 pmMDW-YUL
4h 35m1 stop
$440Porter Airlines
Find Deal
Fri, May 31 - Mon, Jun 3
4:45 pm - 9:37 pmYUL-MDW
5h 52m1 stop
11:25 am - 7:15 pmMDW-YUL
6h 50m1 stop
$457Porter Airlines
Find Deal
Wed, May 29 - Mon, Jun 3
7:00 am - 4:55 pmYUL-MDW
34h 55m2 stops
6:00 am - 12:29 pmMDW-YUL
5h 29m1 stop
$666WestJet
Find Deal
Fri, May 31 - Sun, Jun 2
7:00 am - 4:55 pmYUL-MDW
34h 55m2 stops
6:00 am - 12:29 pmMDW-YUL
5h 29m1 stop
$677WestJet
Find Deal
Fri, May 31 - Sun, Jun 2
6:00 am - 5:06 pmYUL-MDW
12h 06m2 stops
6:00 am - 5:36 pmMDW-YUL
10h 36m1 stop
$707Delta
Find Deal
Fri, May 31 - Mon, Jun 3
6:00 am - 5:06 pmYUL-MDW
12h 06m2 stops
1:21 pm - 11:08 pmMDW-YUL
8h 47m1 stop
$810Delta
Find Deal
Wed, May 29 - Sun, Jun 2
4:45 pm - 9:37 pmYUL-MDW
5h 52m1 stop
7:10 pm - 6:00 pmMDW-YUL
21h 50m2 stops
$835
Find Deal
Wed, May 29 - Fri, May 31
7:00 am - 10:07 amYUL-MDW
4h 07m1 stop
8:56 pm - 12:29 pmMDW-YUL
14h 33m2 stops
$957
Find Deal
Wed, May 29 - Mon, Jun 3

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 flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Montreal to Chicago Midway Airport, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to Montreal, the best deals are generally found on Tuesday, with Monday being the most expensive.

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 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 on average. On the other hand, the most expensive months are September and May, where the average cost of tickets is $455 and $367 respectively.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Porter Airlines ($138) and Delta ($170). The cheapest round-trip tickets were found on Porter Airlines ($233) and Delta ($280).

Good to know

Low season

April

High season

June

Cheapest flight

$138
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 3% 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 $138 for a one-way ticket and $233 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.
7.4
Porter AirlinesOverall score based on 395 reviews
7.4Food
8.2Crew
7.5Comfort
7.6Boarding
6.6Entertainment
Airline reviews

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

10.0 ExcellentJustin, Apr 2024YVR - YYZ
Read more about Porter Airlines reviews

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

Book cheap flights from Montreal to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Montreal to Chicago found on KAYAK in the last 72 hours.
9/6Fri
1 stopPorter Airlines
4h 27mYUL-MDW
$138
9/9Mon
1 stopPorter Airlines
5h 52mYUL-MDW
$144
6/15Sat
1 stopPorter Airlines
3h 57mYUL-MDW
$145
7/2Tue
1 stopPorter Airlines
4h 02mYUL-MDW
$146
9/1Sun
1 stopDelta
10h 01mYUL-MDW
$170
8/31Sat
1 stopWestJet
12h 08mYUL-MDW
$178
6/9Sun
1 stop
19h 26mYUL-MDW
$189
8/11Sun
1 stopDelta
7h 42mYUL-MDW
$191
8/26Mon
2 stopsWestJet
15h 29mYUL-MDW
$201
6/6Thu
1 stop
19h 26mYUL-MDW
$215

Search by stops

Search by airline

Search by price

Last minute flights from Montreal to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Montreal to Chicago that are departing in the next 10 days.
6/2Sun
multi-stopPorter Airlines
6h 37mYUL-MDW
6/9Sun
multi-stopPorter Airlines
4h 40mMDW-YUL
$360
6/2Sun
multi-stopPorter Airlines
4h 02mYUL-MDW
6/9Sun
multi-stopPorter Airlines
4h 05mMDW-YUL
$433
5/31Fri
multi-stopPorter Airlines
4h 02mYUL-MDW
6/3Mon
multi-stopPorter Airlines
4h 35mMDW-YUL
$440
5/29Wed
multi-stopPorter Airlines
5h 52mYUL-MDW
6/3Mon
multi-stopPorter Airlines
6h 50mMDW-YUL
$457
5/31Fri
multi-stopWestJet
34h 55mYUL-MDW
6/2Sun
multi-stopWestJet
5h 29mMDW-YUL
$666
5/31Fri
multi-stopWestJet
34h 55mYUL-MDW
6/2Sun
multi-stopWestJet
5h 29mMDW-YUL
$677
5/31Fri
multi-stopDelta
12h 06mYUL-MDW
6/3Mon
multi-stopDelta
10h 36mMDW-YUL
$707
5/29Wed
multi-stopDelta
12h 06mYUL-MDW
6/2Sun
multi-stopDelta
8h 47mMDW-YUL
$810
5/29Wed
multi-stop
5h 52mYUL-MDW
5/31Fri
multi-stop
21h 50mMDW-YUL
$835
5/29Wed
multi-stop
4h 07mYUL-MDW
6/3Mon
multi-stop
14h 33mMDW-YUL
$957

Search by stops

Search by airline

Search by price

Montreal - Chicago Midway Airport Flights

Departure:

Montreal (YUL)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Montreal

Cabin classes:

Browse origins:

Browse destinations: