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Cheap Flights from Toronto to Chicago from $180

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Cheap YTZ to MDW Flights

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

Wed, Jul 3 - Sat, Jul 6
YTZ
Toronto
to
MDW
Chicago
$180

roundtrip

found 5 days ago

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Tue, Jul 16 - Sat, Jul 27
YTZ
Toronto
to
MDW
Chicago
$182

roundtrip

found 5 days ago

Open YTZ to MDW flights search result page
Tue, Jul 2 - Sat, Jul 6
YTZ
Toronto
to
MDW
Chicago
$193

roundtrip

found 5 days ago

Open YTZ to MDW flights search result page
Mon, Jul 22 - Tue, Jul 30
YTZ
Toronto
to
MDW
Chicago
$195

roundtrip

found 1 day ago

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Wed, Jul 3 - Fri, Jul 5
YTZ
Toronto
to
MDW
Chicago
$197

roundtrip

found 5 days ago

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Mon, Jul 15 - Sat, Jul 27
YTZ
Toronto
to
MDW
Chicago
$199

roundtrip

found 5 days ago

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Mon, Jul 15 - Sat, Jul 20
YTZ
Toronto
to
MDW
Chicago
$204

roundtrip

found 1 day ago

Open YTZ to MDW flights search result page
Thu, Jul 4 - Sun, Jul 7
YTZ
Toronto
to
MDW
Chicago
$206

roundtrip

found 6 days ago

Open YTZ to MDW flights search result page
Fri, Sep 6 - Sun, Sep 8
YTZ
Toronto
to
MDW
Chicago
$207

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just found

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Sun, Nov 17 - Thu, Nov 21
YTZ
Toronto
to
MDW
Chicago
$208

roundtrip

found 3 days ago

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Tue, Jul 2 - Fri, Jul 5
YTZ
Toronto
to
MDW
Chicago
$210

roundtrip

found 5 days ago

Open YTZ to MDW flights search result page
Mon, Jul 22 - Tue, Jul 30
YTZ
Toronto
to
MDW
Chicago
$211

roundtrip

found 1 day ago

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Sun, Jul 28 - Mon, Jul 29
YTZ
Toronto
to
MDW
Chicago
$215

roundtrip

found 5 days ago

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Wed, Jul 3 - Mon, Jul 8
YTZ
Toronto
to
MDW
Chicago
$216

roundtrip

found 4 days ago

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Fri, Jul 19 - Wed, Jul 24
YTZ
Toronto
to
MDW
Chicago
$220

roundtrip

found 1 day ago

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Wed, Jun 26 - Wed, Jul 3
YTZ
Toronto
to
MDW
Chicago
$223

roundtrip

found 4 days ago

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Mon, Aug 5 - Thu, Aug 8
YTZ
Toronto
to
MDW
Chicago
$224

roundtrip

found 2 hours ago

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Wed, Jul 3 - Tue, Jul 30
YTZ
Toronto
to
MDW
Chicago
$226

roundtrip

found 1 day ago

Open YTZ to MDW flights search result page
Sun, Aug 18 - Wed, Aug 21
YTZ
Toronto
to
MDW
Chicago
$228

roundtrip

found 3 days ago

Open YTZ to MDW flights search result page
Wed, Jun 26 - Wed, Jul 3
YTZ
Toronto
to
MDW
Chicago
$229

roundtrip

found 6 days ago

Open YTZ to MDW flights search result page

Toronto to Chicago route information

Origin Airport Billy Bishop Toronto City
Destination Airport Midway Intl.
Airlines Serving Porter Airlines
Flight Price $180
Distance 442 mi

Niagara Falls

IAG-Niagara Falls Intl.

$9,942.66

Toronto

YYZ-Pearson Intl.

$218.53

Chicago

ORD-O'Hare Intl.

$256.99

Top Routes from Toronto

Top Routes to Chicago

Cheap YTZ to MDW Flights

  • Question : What is the cheapest airline flying from Toronto to Chicago?
    Answer : Porter Airlines is your best bet for finding that sought-after low fare. They're offering fares as low as $192, while prices for other flights are as high as $347.
  • Question : Which airline has the least delays from Toronto to Chicago?
    Answer : Porter Airlines holds the best record for flights from YTZ to MDW with a 64% on-time rate. If they are delayed for some reason, expect it to be an 18-minute delay, as that’s the average.
  • Question : Can I change the date of my flight?
    Answer : Yes, you can change your departure date. If you want to save a little money in doing so, the lowest-cost day to fly in June is Wednesday. Being flexible with your travel days can provide you extra savings when booking.
  • Question : How many flights are there per day from Toronto to Chicago?
    Answer : The number of flight times varies by day, but on average, YTZ to MDW sees 11 different choices. That is higher than the national average of six.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from Toronto to Chicago is on Wednesday. So, if you are trying to save a little money on your next vacation look for flights on that day.
  • Question : What day of the week has the most flight time options?
    Answer : With 12 total flight time options, Monday provides the most flexibility from YTZ to MDW. The day of the week with the least amount of times is Saturday with only seven options.
  • Question : How long does it take to fly from Toronto to Chicago?
    Answer : Flying from YTZ to MDW typically takes about one hour and 50 minutes. Remember, there is a one-hour time change.