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YUL - MDW

C$ 176 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 8/3. 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

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
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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.

Recent round-trip flight deals from Montreal to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Montreal to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
11:15 a.m. - 6:00 p.m.MDW-YUL
5h 45m1 stop
C$ 272Porter Airlines
Find Deal
vie., 21 mar. - dom., 23 mar.
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 276Porter Airlines
Find Deal
mié., 5 mar. - mié., 12 mar.
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 278Porter Airlines
Find Deal
lun., 3 mar. - mié., 5 mar.
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
5:35 p.m. - 10:45 p.m.MDW-YUL
4h 10m1 stop
C$ 298Porter Airlines
Find Deal
vie., 7 mar. - vie., 14 mar.
6:00 a.m. - 12:42 p.m.YUL-MDW
7h 42m1 stop
2:08 p.m. - 11:22 p.m.MDW-YUL
8h 14m1 stop
C$ 353Delta
Find Deal
jue., 20 feb. - lun., 24 feb.
12:49 p.m. - 6:11 p.m.YUL-MDW
6h 22m1 stop
6:28 p.m. - 11:22 p.m.MDW-YUL
3h 54m1 stop
C$ 386Delta
Find Deal
jue., 20 feb. - lun., 24 feb.
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
12:26 p.m. - 11:15 a.m.MDW-YUL
21h 49m2 stops
C$ 411
Find Deal
mié., 5 mar. - mié., 12 mar.
8:55 a.m. - 5:33 p.m.YUL-MDW
9h 38m2 stops
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 433
Find Deal
lun., 3 mar. - mié., 5 mar.
6:00 p.m. - 5:59 p.m.YUL-MDW
24h 59m1 stop
7:00 p.m. - 12:39 a.m.MDW-YUL
28h 39m2 stops
C$ 469WestJet
Find Deal
vie., 18 abr. - lun., 21 abr.
6:45 a.m. - 9:09 a.m.YUL-MDW
27h 24m2 stops
7:09 p.m. - 11:39 p.m.MDW-YUL
27h 30m1 stop
C$ 496WestJet
Find Deal
mar., 11 mar. - vie., 14 mar.

Flights from Montreal to Chicago - Travel Insights & Trends

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 May, where tickets cost C$ 365 (return) on average. On the other hand, the most expensive months are October and December, where the average cost of round-trip tickets is C$ 617 and C$ 468 respectively.

Good to know

Low season

April

High season

December

Cheapest flight

C$ 176
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (6% 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$ 123 for a one-way ticket and C$ 190 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.

  • 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 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.

See more FAQs

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.
7.9
Porter AirlinesOverall score based on 277 reviews
8.7Crew
8.2Boarding
7.6Food
8.0Comfort
7.0Entertainment
Airline reviews

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.

8.0 ExcellentJason, Dec 2024YUL - YHZ
Read more Porter Airlines reviews

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.

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.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
New Buffalo
Portage
Merrillville
Schererville
Saint Joseph
Valparaiso
Hammond
Munster
Chesterton
Lansing
Monticello
Porter

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

Information on your arrival and departure airports

Midway (MDW)
Montreal (YUL)

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