$140 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 $140 for one-way flights and $237 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Sun, Jun 16 - Sun, Jul 21
YTZ
Toronto
MDW
Chicago
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Jun 16 from Toronto to Chicago, returning Sun, Jul 21, priced at $237 just found
Porter Airlines
Tue, May 28 - Tue, Jun 4
YTZ
Toronto
MDW
Chicago
$238 Roundtrip, found 22 hours ago
$238
Roundtrip
found 22 hours ago
Select Porter Airlines flight, departing Tue, May 28 from Toronto to Chicago, returning Tue, Jun 4, priced at $238 found 22 hours ago
Porter Airlines
Mon, May 27 - Sat, Jun 1
YTZ
Toronto
MDW
Chicago
$252 Roundtrip, found 6 days ago
$252
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Mon, May 27 from Toronto to Chicago, returning Sat, Jun 1, priced at $252 found 6 days ago
Porter Airlines
Fri, Jun 7 - Fri, Jun 14
YTZ
Toronto
MDW
Chicago
$269 Roundtrip, found 3 hours ago
$269
Roundtrip
found 3 hours ago
Select Porter Airlines flight, departing Fri, Jun 7 from Toronto to Chicago, returning Fri, Jun 14, priced at $269 found 3 hours ago
Porter Airlines
Mon, May 20 - Wed, May 29
YTZ
Toronto
MDW
Chicago
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Mon, May 20 from Toronto to Chicago, returning Wed, May 29, priced at $270 found 3 days ago
Porter Airlines
Thu, Jun 13 - Wed, Jun 19
YTZ
Toronto
MDW
Chicago
$272 Roundtrip, found 6 days ago
$272
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Thu, Jun 13 from Toronto to Chicago, returning Wed, Jun 19, priced at $272 found 6 days ago
Porter Airlines
Fri, Jun 14 - Mon, Jun 17
YTZ
Toronto
MDW
Chicago
$274 Roundtrip, found 4 days ago
$274
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Jun 14 from Toronto to Chicago, returning Mon, Jun 17, priced at $274 found 4 days ago
Porter Airlines
Mon, Jul 1 - Tue, Jul 30
YTZ
Toronto
MDW
Chicago
$277 Roundtrip, found 1 hour ago
$277
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Mon, Jul 1 from Toronto to Chicago, returning Tue, Jul 30, priced at $277 found 1 hour ago
Porter Airlines
Tue, May 28 - Sun, Jun 9
YTZ
Toronto
MDW
Chicago
$278 Roundtrip, found 22 hours ago
$278
Roundtrip
found 22 hours ago
Select Porter Airlines flight, departing Tue, May 28 from Toronto to Chicago, returning Sun, Jun 9, priced at $278 found 22 hours ago
Porter Airlines
Fri, May 24 - Mon, May 27
YTZ
Toronto
MDW
Chicago
$281 Roundtrip, found 6 days ago
$281
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Fri, May 24 from Toronto to Chicago, returning Mon, May 27, priced at $281 found 6 days ago
0
Flights from Toronto (YTZ) to Chicago (MDW)
Origin airport
Billy Bishop Toronto City
Destination airport
Midway Intl.
Airlines serving
Porter Airlines
Roundtrip price
$236
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 $140 now!

Frequently asked questions

How much is a one-way flight from Billy Bishop Toronto City Airport (YTZ) to Chicago Airport?
Get ready to pack your bags, because Toronto flights to Chicago start from only $143. This information is based on the cheapest price found on Expedia for this route departing in the next three months. This airfare is for an Porter Airlines flight, departing YTZ on June 9 2024 and arriving at MDW. The price of this airfare was updated on May 7 2024 and has not changed since.
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 is the cheapest airline flying from Billy Bishop Airport to Midway Intl. Airport (MDW) in the next 90 days?
With tickets starting at $143 for a flight from Toronto to Chicago, Porter Airlines is the cheapest airline found on Expedia. This price is based on airfares found on Expedia departing within the next 90 days and was updated on May 7 2024 and has not changed since. The flight takes off from Billy Bishop Toronto City Airport (YTZ) on June 9 2024 and arrives at Chicago Airport.
What's the cheapest price for a flight from Billy Bishop Airport to Midway Airport next month?
The cheapest price for a flight from Toronto to Chicago over the next month is $145. If you’re thinking about traveling soon, now’s the time to reel in this fare. This price was found after looking through all available flights on Expedia departing within the next 30 days. This fare is for a one-way Porter Airlines flight journeying from Billy Bishop Airport on June 2 2024 and getting into Midway Airport. Pricing info was updated on May 7 2024 and has not changed since.
Can I find cheap nonstop flights from Billy Bishop Toronto City Airport (YTZ) to MDW in the next three months?
The cheapest fare we’ve found for a roundtrip nonstop flight from Toronto to Chicago within the next 90 days is $242. This price was found after searching available flights on Expedia with a departure date within the next three months. This airfare is for a flight via Porter Airlines jetting off from Billy Bishop Toronto City Airport (YTZ) on May 29 2024 and arriving at Midway Airport, with a return flight on May 31 2024. Pricing information was last updated on May 7 2024.Use our handy filters to hunt for nonstop cheap flights from YTZ to Midway Airport. Simply click on “Nonstop” under “Filter by” once you see your search results. Open to flying on a different date? You can also try the “Flexible dates” dropdown menu to review ticket prices for nearby days. Finding a flight that fits your budget and timetable couldn’t be easier.
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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