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Cheap Flights from Chicago to Toronto from $246

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Cheap MDW to YYZ Flights

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

Wed, Oct 2 - Wed, Oct 9
MDW
Chicago
to
YYZ
Toronto
$246

roundtrip

found 3 days ago

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Wed, Oct 30 - Sat, Nov 2
MDW
Chicago
to
YYZ
Toronto
$248

roundtrip

found 4 days ago

Open MDW to YYZ flights search result page
Sat, Nov 30 - Wed, Dec 4
MDW
Chicago
to
YYZ
Toronto
$252

roundtrip

found 2 days ago

Open MDW to YYZ flights search result page
Thu, Nov 7 - Tue, Nov 12
MDW
Chicago
to
YYZ
Toronto
$252

roundtrip

found 5 hours ago

Open MDW to YYZ flights search result page
Sat, Sep 7 - Tue, Sep 10
MDW
Chicago
to
YYZ
Toronto
$262

roundtrip

found 4 days ago

Open MDW to YYZ flights search result page
Wed, Oct 2 - Wed, Oct 9
MDW
Chicago
to
YYZ
Toronto
$263

roundtrip

found 3 days ago

Open MDW to YYZ flights search result page
Wed, Oct 2 - Wed, Oct 9
MDW
Chicago
to
YYZ
Toronto
$265

roundtrip

found 3 days ago

Open MDW to YYZ flights search result page
Sat, Sep 7 - Tue, Sep 10
MDW
Chicago
to
YYZ
Toronto
$266

roundtrip

found 4 days ago

Open MDW to YYZ flights search result page
Wed, Oct 30 - Sat, Nov 2
MDW
Chicago
to
YYZ
Toronto
$268

roundtrip

found 4 days ago

Open MDW to YYZ flights search result page
Sat, Nov 30 - Wed, Dec 4
MDW
Chicago
to
YYZ
Toronto
$269

roundtrip

found 2 days ago

Open MDW to YYZ flights search result page
Mon, Dec 2 - Fri, Dec 6
MDW
Chicago
to
YYZ
Toronto
$269

roundtrip

found 12 hours ago

Open MDW to YYZ flights search result page
Thu, Nov 7 - Tue, Nov 12
MDW
Chicago
to
YYZ
Toronto
$270

roundtrip

found 5 hours ago

Open MDW to YYZ flights search result page
Tue, Sep 17 - Sat, Sep 21
MDW
Chicago
to
YYZ
Toronto
$271

roundtrip

found 4 hours ago

Open MDW to YYZ flights search result page
Thu, Dec 5 - Sun, Dec 8
MDW
Chicago
to
YYZ
Toronto
$273

roundtrip

found 12 hours ago

Open MDW to YYZ flights search result page
Mon, Nov 25 - Fri, Nov 29
MDW
Chicago
to
YYZ
Toronto
$282

roundtrip

found 4 days ago

Open MDW to YYZ flights search result page
Sat, Sep 7 - Tue, Sep 10
MDW
Chicago
to
YYZ
Toronto
$282

roundtrip

found 4 days ago

Open MDW to YYZ flights search result page
Tue, Sep 24 - Tue, Oct 1
MDW
Chicago
to
YYZ
Toronto
$290

roundtrip

found 13 hours ago

Open MDW to YYZ flights search result page
Thu, Feb 13 - Sun, Feb 16
MDW
Chicago
to
YYZ
Toronto
$290

roundtrip

found 1 day ago

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to route information

Airlines Serving Delta, WestJet

Chicago

ORD-O'Hare Intl.

$216.19

Top Routes from Chicago

Top Routes to Toronto

Cheap MDW to YYZ Flights

  • Question : What airports do you fly into for Toronto?
    Answer : Departing from Chicago Midway International Airport is not the only way to get to Pearson International Airport. Try looking for flights from O'Hare International Airport (ORD). Over the next two months, flights from ORD to YYZ are being booked 37% cheaper than flights from MDW to YYZ. Being just 16 miles away, it's easily accessible for most.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from Chicago to Toronto is on Monday. So, if you are trying to save a bit of cash on your next flight look for flights on that day.
  • Question : What is the cheapest airline flying from Chicago to Toronto?
    Answer : Delta Air Lines is offering the best deal at $244. Better book fast because prices range all the way up to $782 over the next three months.
  • Question : Can I change the date of my flight?
    Answer : You sure can and you may save money by changing when you leave. The lowest-cost day to fly in July is Monday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.
  • Question : How much is a plane ticket to Toronto (YYZ) from Chicago (MDW)?
    Answer : They can range from $244 to $782. Booking in advance can usually help you get the cheapest rate. Remember, you can save by booking well in advance.
  • Question : Is there an alternative airport near Toronto?
    Answer : Pearson International Airport is a fine airport, but there is a cheaper option – Billy Bishop Toronto City Airport. It’s only 11 miles away and flights are being booked 47% cheaper over the coming two months.
  • Question : How long does the average person stay in Toronto?
    Answer : Of course, you're not an average person, but if you were, you'd stay roughly four days.