$138 Cheap Flights from Toronto (YTZ) to Chicago (MDW)

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Cheap Flights from Toronto to Chicago (YTZ-MDW)

Prices were available within the past 7 days and start at $138 for one-way flights and $221 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Porter Airlines
Porter Airlines
Porter Airlines
Porter Airlines
Porter Airlines
Porter Airlines
Porter Airlines
Porter Airlines
Porter Airlines
Flights from Toronto (YTZ) to Chicago (MDW)
Origin airport
Billy Bishop Toronto City
Destination airport
Midway Intl.
Airlines serving
Porter Airlines
Roundtrip price
$220
Distance
442 mi

Toronto to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Toronto to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Toronto to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from YTZ to MDW today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is $138 now!

Frequently asked questions

How long does it take to fly from YTZ to Chicago Airport?
Porter Airlines has a direct flight departing from YTZ at 11:45AM and reaching MDW at 12:32PM — a travel time of 1 hour and 47 minutes. Pick the seat that’s right for you, pack a few things to keep you busy and the time will zip by.
Is it cheaper to buy a plane ticket from Billy Bishop Airport to Midway Intl. Airport (MDW) last minute?
Booking your flight from Billy Bishop Toronto City Airport (YTZ) to MDW last minute could save you cash if you hit the jackpot and find an epic deal. However, tickets don’t typically get cheaper as the departure date nears. If you hold off, flights could also be booked up or the best seats gone (because no one wants the middle seat). If you’d rather play it safe, book well in advance of when you want to leave. Note that some of the biggest deals can be found up to 12 months in advance. If your favorite airline hasn’t released tickets yet, check back regularly as offers are updated on Expedia all the time.
What airports do you fly into for Chicago from Toronto?
From Toronto, you can connect to Chicago via Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT). Research which airport is right for you before making your decision. If you go with Midway Intl. Airport (MDW), it’s around 9 mi southwest of downtown. Use the money you save when booking your ticket with Expedia to enjoy the city’s top sights, such as Wrigley Field and Millennium Park.
What are the most popular departure times for flights from Billy Bishop Airport to Midway Airport?
The most popular departure times for flights from Billy Bishop Airport to Chicago Airport fall between 3:00 PM - 4:00 PM on Porter Airlines. Our recommendation is to head out in the morning. The earlier you travel, the better your chances of a delay-free flight with lighter air traffic in the sky.
Can I change the date of my flight from YTZ to MDW?
You can easily make changes to your Billy Bishop Airport to Chicago Airport trip through the Expedia Trips portal. But before doing so, review the fare conditions in your itinerary to find out what the carrier will let you do and what fees apply for changes. Some carriers charge a change fee per person, in addition to any difference in fares. However, if you booked in the last 24 hours, you may be able to cancel for free and organize new flights. You can also find your way to our Customer Service portal for more advice and to chat with our Virtual Agent.
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