Find cheap flights from Toronto Island to Chicago from C$ 191

• The cheapest flight from Toronto Island to Chicago was found, on average, 88 days before departure.
• Book at least 3 weeks before departure in order to get a below-average price.
• High season is considered to be July, August and September. The cheapest month to fly is January.
• Morning departure is around 126% more expensive than an evening flight, on average*.

• How long does a flight from Toronto Island to Chicago take?

  Direct flights cover the 700 km separating Toronto Island to Chicago in about 1h 47m.

• How many flights are there between Toronto Island and Chicago?

  There are usually 2 direct flights each day leaving Toronto Island in the direction of Chicago, for a total of 20 flights weekly.

• Which airlines provide the cheapest flights from Toronto Island to Chicago?

  In the last 3 days, Porter Airlines offered the best one-way deal for that route, at C$ 256. KAYAK users also found Toronto Island to Chicago round-trip flights on Porter Airlines from C$ 414 and on Air Canada from C$ 639.

• What’s the cheapest day of the week to fly from Toronto Island to Chicago?

  When flying from Toronto Island to Chicago, you should consider leaving on a Sunday and avoid Saturdays if you are looking for the best rates. For your return to Toronto Island, you’ll find the best rates on Fridays and the most expensive ones on Wednesdays.

• Which airports will I be using when flying from Toronto Island to Chicago?

  Toronto Island is served by only 1 airport and there are 2 airports in Chicago. You will leave Toronto Island from Toronto Island and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

• What’s the earliest departure time from Toronto Island to Chicago?

  The earliest flight leaves Toronto Island at 9:30 am and lands in Chicago at 10:17 am.

• What’s the latest departure time from Toronto Island to Chicago?

  The last flight leaves Toronto Island at 8:45 pm and lands in Chicago at 9:32 pm.

• Which airlines fly direct between Toronto Island and Chicago?

  Porter Airlines is the only airline operating direct flights from Toronto Island to Chicago.

• Which aircraft models fly most regularly from Toronto Island to Chicago?

  The Boeing 737-800 is the aircraft model that flies most regularly on the Toronto Island to Chicago flight route.

• On which days can I fly direct from Toronto Island to Chicago?

  There are direct flights from Toronto Island to Chicago on a daily basis.

• Which airlines have a flexible cancellation policy for flights from Toronto Island to Chicago due to COVID-19?

  Porter Airlines has waived its change and cancellation fees on flights from Toronto Island to Chicago. Confirm policy on booking site.

• How does KAYAK find such low prices on flights from Toronto Island to Chicago?

  KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto Island to Chicago.

• How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto Island to Chicago?

  KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Toronto Island is likely to change within 7 days, so travellers know whether to wait or book now.

• What is the Hacker Fare option on flights from Toronto Island to Chicago?

  Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Toronto Island with another airline.

• What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Island to Chicago?

  Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Toronto Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Book cheap flights from Toronto Island to Chicago

Recent round-trip flight deals

18/6Sun

directPorter Airlines

1h 47mYTZ-MDW

20/6Tue

directPorter Airlines

1h 42mMDW-YTZ

C$ 309

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28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

3/7Mon

directPorter Airlines

1h 42mMDW-YTZ

C$ 352

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29/6Thu

directPorter Airlines

1h 47mYTZ-MDW

1/7Sat

directPorter Airlines

1h 42mMDW-YTZ

C$ 354

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29/6Thu

directPorter Airlines

1h 47mYTZ-MDW

3/7Mon

directPorter Airlines

1h 42mMDW-YTZ

C$ 358

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5/7Wed

directPorter Airlines

1h 47mYTZ-MDW

7/7Fri

directPorter Airlines

1h 42mMDW-YTZ

C$ 373

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26/7Wed

directPorter Airlines

1h 47mYTZ-MDW

2/8Wed

directPorter Airlines

1h 42mMDW-YTZ

C$ 377

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1/7Sat

directPorter Airlines

1h 47mYTZ-MDW

4/7Tue

directPorter Airlines

1h 42mMDW-YTZ

C$ 381

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29/6Thu

directPorter Airlines

1h 47mYTZ-MDW

3/7Mon

directPorter Airlines

1h 42mMDW-YTZ

C$ 391

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28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

4/7Tue

directPorter Airlines

1h 42mMDW-YTZ

C$ 397

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1/7Sat

directPorter Airlines

1h 47mYTZ-MDW

7/7Fri

directPorter Airlines

1h 42mMDW-YTZ

C$ 409

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11/10Wed

1 stopAir Canada

5h 23mYTZ-ORD

19/10Thu

1 stopAir Canada

4h 30mORD-YTZ

C$ 476

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5/9Tue

1 stopAir Canada

5h 23mYTZ-ORD

9/9Sat

1 stopAir Canada

4h 34mORD-YTZ

C$ 502

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12/7Wed

1 stopAir Canada

5h 18mYTZ-ORD

18/7Tue

1 stopAir Canada

4h 56mORD-YTZ

C$ 517

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5/9Tue

1 stopAir Canada

5h 23mYTZ-ORD

11/9Mon

1 stopAir Canada

4h 34mORD-YTZ

C$ 525

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26/7Wed

1 stopAir Canada

5h 18mYTZ-ORD

29/7Sat

1 stopAir Canada

4h 56mORD-YTZ

C$ 541

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10/7Mon

1 stopAir Canada

13h 34mYTZ-ORD

18/7Tue

1 stopAir Canada

6h 56mORD-YTZ

C$ 554

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6/9Wed

2 stopsMultiple Airlines

17h 11mYTZ-ORD

10/9Sun

2 stopsMultiple Airlines

12h 45mORD-YTZ

C$ 612

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6/7Thu

2 stopsMultiple Airlines

37h 04mYTZ-ORD

9/7Sun

2 stopsMultiple Airlines

34h 55mORD-YTZ

C$ 730

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24/6Sat

2 stopsMultiple Airlines

12h 00mYTZ-ORD

27/6Tue

2 stopsMultiple Airlines

24h 40mORD-YTZ

C$ 745

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24/6Sat

3 stopsMultiple Airlines

19h 30mYTZ-ORD

27/6Tue

2 stopsMultiple Airlines

24h 40mORD-YTZ

C$ 746

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C$ 360 or lessC$ 390 or lessC$ 500 or lessC$ 550 or lessC$ 750 or less

Recent one-way flight deals

28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

C$ 191

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28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

C$ 197

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28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

C$ 208

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3/7Mon

directPorter Airlines

1h 47mYTZ-MDW

C$ 209

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29/10Sun

directPorter Airlines

1h 50mYTZ-MDW

C$ 213

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10/7Mon

directPorter Airlines

1h 47mYTZ-MDW

C$ 220

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20/6Tue

directPorter Airlines

1h 47mYTZ-MDW

C$ 230

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3/7Mon

directPorter Airlines

1h 47mYTZ-MDW

C$ 238

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12/7Wed

1 stopAir Canada

5h 18mYTZ-ORD

C$ 248

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9/8Wed

1 stopAir Canada

5h 18mYTZ-ORD

C$ 258

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21/6Wed

1 stopAir Canada

5h 18mYTZ-ORD

C$ 264

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22/6Thu

2 stopsMultiple Airlines

18h 27mYTZ-ORD

C$ 270

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13/9Wed

1 stopAir Canada

5h 23mYTZ-ORD

C$ 274

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16/9Sat

1 stopAir Canada

5h 33mYTZ-ORD

C$ 276

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27/6Tue

2 stopsMultiple Airlines

15h 10mYTZ-MDW

C$ 283

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17/9Sun

1 stopAir Canada

5h 23mYTZ-ORD

C$ 286

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10/9Sun

1 stopAir Canada

5h 23mYTZ-ORD

C$ 287

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18/7Tue

2 stopsMultiple Airlines

10h 19mYTZ-ORD

C$ 289

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18/9Mon

2 stopsMultiple Airlines

9h 39mYTZ-ORD

C$ 323

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21/6Wed

2 stopsMultiple Airlines

15h 38mYTZ-MDW

C$ 346

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Direct1 stop2+ stops

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C$ 210 or lessC$ 240 or lessC$ 270 or lessC$ 290 or lessC$ 350 or less