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YUL - MDW

$153 Find cheap flights from Montreal Pierre Elliott Trudeau Intl Airport 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 5/20. 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
Sun 5/26
Sun 6/2

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 44,738,066 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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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)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montreal to Midway 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 and deals for you by selecting your travel dates.
Choose your dates
3:10 pm - 7:02 pmYUL-MDW
4h 52m1 stop
12:30 pm - 6:45 pmMDW-YUL
5h 15m1 stop
$239Porter Airlines
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Sat, May 25 - Sat, Jun 1
12:50 pm - 4:17 pmYUL-MDW
4h 27m1 stop
8:40 am - 3:30 pmMDW-YUL
5h 50m1 stop
$245Porter Airlines
Find Deal
Fri, May 24 - Sun, May 26
3:10 pm - 7:02 pmYUL-MDW
4h 52m1 stop
12:15 pm - 7:15 pmMDW-YUL
6h 00m1 stop
$246Porter Airlines
Find Deal
Sat, May 25 - Sun, May 26
10:45 am - 4:17 pmYUL-MDW
6h 32m1 stop
12:15 pm - 7:15 pmMDW-YUL
6h 00m1 stop
$247Porter Airlines
Find Deal
Fri, May 24 - Sun, May 26
6:14 am - 11:02 amYUL-MDW
5h 48m1 stop
2:15 pm - 11:30 pmMDW-YUL
8h 15m1 stop
$267Delta
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Sun, May 26 - Tue, Jun 4
6:00 am - 8:48 amYUL-MDW
3h 48m1 stop
1:24 pm - 11:04 pmMDW-YUL
8h 40m1 stop
$310Delta
Find Deal
Thu, Jun 13 - Sun, Jun 16
7:10 am - 12:40 pmYUL-MDW
6h 30m1 stop
12:15 pm - 7:15 pmMDW-YUL
6h 00m1 stop
$334
Find Deal
Fri, May 24 - Sun, May 26
6:14 am - 6:07 pmYUL-MDW
12h 53m1 stop
8:00 am - 1:45 pmMDW-YUL
4h 45m1 stop
$343
Find Deal
Thu, May 23 - Mon, May 27
12:45 pm - 5:14 pmYUL-MDW
5h 29m1 stop
2:05 pm - 11:40 pmMDW-YUL
8h 35m1 stop
$363WestJet
Find Deal
Sat, Aug 17 - Sat, Aug 24
6:47 pm - 5:59 pmYUL-MDW
24h 12m1 stop
3:45 pm - 8:15 pmMDW-YUL
27h 30m2 stops
$364WestJet
Find Deal
Tue, Jun 11 - Tue, Jun 18

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.

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 ($153) and Delta ($192). The cheapest round-trip tickets were found on Porter Airlines ($239) and Delta ($267).

Good to know

Low season

January

High season

May

Cheapest flight

$153
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 1% 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 $153 for a one-way ticket and $239 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 438 reviews
7.5comfort
7.4food
7.6boarding
8.2crew
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.

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

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

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.
5/20Mon
1 stopPorter Airlines
4h 27mYUL-MDW
$153
5/18Sat
1 stopPorter Airlines
4h 52mYUL-MDW
$157
6/16Sun
1 stopPorter Airlines
6h 27mYUL-MDW
$168
5/16Thu
1 stopPorter Airlines
4h 07mYUL-MDW
$169
7/2Tue
1 stopDelta
3h 49mYUL-MDW
$192
6/16Sun
2 stopsWestJet
15h 40mYUL-MDW
$208
5/20Mon
2 stops
11h 45mYUL-MDW
$236
6/27Thu
2 stopsWestJet
22h 21mYUL-MDW
$246
5/2Thu
2 stops
31h 24mYUL-MDW
$283
5/18Sat
2 stopsDelta
11h 03mYUL-MDW
$329

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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.
5/1Wed
multi-stopPorter Airlines
5h 52mYUL-MDW
5/4Sat
multi-stopPorter Airlines
5h 35mMDW-YUL
$431
5/1Wed
multi-stopPorter Airlines
4h 07mYUL-MDW
5/4Sat
multi-stopPorter Airlines
5h 35mMDW-YUL
$446
4/29Mon
multi-stopPorter Airlines
6h 32mYUL-MDW
5/6Mon
multi-stopPorter Airlines
4h 45mMDW-YUL
$454
4/30Tue
multi-stopPorter Airlines
4h 07mYUL-MDW
5/4Sat
multi-stopPorter Airlines
5h 35mMDW-YUL
$487
4/29Mon
multi-stopPorter Airlines
4h 27mYUL-MDW
5/1Wed
multi-stopPorter Airlines
3h 55mMDW-YUL
$501
5/1Wed
multi-stopPorter Airlines
6h 32mYUL-MDW
5/2Thu
multi-stopPorter Airlines
3h 55mMDW-YUL
$502
4/27Sat
multi-stopPorter Airlines
4h 52mYUL-MDW
4/30Tue
multi-stopPorter Airlines
4h 45mMDW-YUL
$545
4/27Sat
multi-stopPorter Airlines
4h 52mYUL-MDW
4/29Mon
multi-stopPorter Airlines
3h 55mMDW-YUL
$546
4/27Sat
multi-stopPorter Airlines
4h 52mYUL-MDW
4/30Tue
multi-stopPorter Airlines
4h 45mMDW-YUL
$576

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Montreal - Chicago Midway Airport Flights

Departure:

Montreal (YUL)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Montreal

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