Skip to main content
Beginning of main content

YUL (Montreal) to MDW (Chicago) Flights $249.92

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap YUL to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

$276.10

Interesting Facts About Flights from Montreal to Chicago (YUL to MDW)

Question : Do prices fluctuate more for this route than others?
Answer : Ranging from $259 to $310, prices for YUL to MDW change a lot less than most routes from Canada. Prices tend to be lower the further out you book.

Question : Over the coming months, which airline is getting their passengers to Chicago Midway International Airport (MDW) round-trip the cheapest?
Answer : Porter Airlines is your best bet for finding that coveted low fare. They're offering fares as low as $259, while prices for other flights are as high as $310.

Question : If punctuality is required for you to book a flight, which airline is your best bet?
Answer : Air Canada will have you to MDW on schedule 100% of the time. Don't spend more time waiting in an airport than you have to and stick with Air Canada on this route. Perfection is hard to come by, so hopefully it continues.

Question : In terms of overall promptness, how does YUL to MDW rank compared to the rest of the world?
Answer : Using the combined on-time percentage and average delay breakdown, Montreal to Chicago currently has a 1 out of a possible 5 star rating. A 1-star rating means you should feel rather worried about getting to Chicago on time.

Question : In the next four weeks, what day should you book your trip?
Answer : Since low prices are preferred, look at Jul 28th. As of Jul 17th, it's showing the cheapest ticket sales at $259. That is 7% below the average price for this route, so you can spend that extra cash on an adventure in Chicago.

Question : Which airline can you expect delays with on this route?
Answer : 100% of Flexjet flights from Montreal-Pierre Elliott Trudeau International Airport (YUL) to Chicago Midway International Airport (MDW) are delayed. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : Will you do what it takes to get the absolute cheapest flight?
Answer : The cheapest day to fly in August is Tuesday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.