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Flights from Toronto to Chicago
Flight deals from Toronto to Chicago
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Round-trip
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One way
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Cheapest nonstopYTZ 16:051h 49mDirectMDW 16:54Toronto - Chicago | Mon, Jun 9 | Porter AirlinesMDW 09:401h 40mDirectYTZ 12:20Chicago - Toronto | Thu, Jun 12 | Porter Airlines£93 £12827% OFF27% OFF£128 £93
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YTZ 16:051h 49mDirectMDW 16:54Toronto - Chicago | Sun, Jun 15 | Porter AirlinesMDW 09:401h 42mDirectYTZ 12:22Chicago - Toronto | Tue, Jun 17 | Porter Airlines£94 £12827% OFF27% OFF£128 £94
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Sat, Jun 7 | Porter AirlinesMDW 09:401h 42mDirectYTZ 12:22Chicago - Toronto | Sat, Jun 14 | Porter Airlines£94 £12827% OFF27% OFF£128 £94
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Sat, May 24 | Porter AirlinesMDW 09:401h 42mDirectYTZ 12:22Chicago - Toronto | Sun, May 25 | Porter Airlines£9426% OFF£128 £94
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Mon, May 19 | Porter AirlinesMDW 09:401h 42mDirectYTZ 12:22Chicago - Toronto | Sun, May 25 | Porter Airlines£9823% OFF£128 £98
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Mon, Jun 2 | Porter AirlinesMDW 17:201h 42mDirectYTZ 20:02Chicago - Toronto | Tue, Jun 10 | Porter Airlines£10022% OFF£128 £100
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Tue, Jun 17 | Porter AirlinesMDW 17:201h 42mDirectYTZ 20:02Chicago - Toronto | Tue, Jun 24 | Porter Airlines£10022% OFF£128 £100
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Thu, May 22 | Porter AirlinesMDW 09:401h 42mDirectYTZ 12:22Chicago - Toronto | Mon, May 26 | Porter Airlines£10021% OFF£128 £100
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Fri, May 23 | Porter AirlinesMDW 09:401h 42mDirectYTZ 12:22Chicago - Toronto | Sun, May 25 | Porter Airlines£10319% OFF£128 £103
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YTZ 16:051h 49mDirectMDW 16:54Toronto - Chicago | Fri, Jun 6 | Porter AirlinesMDW 09:401h 42mDirectYTZ 12:22Chicago - Toronto | Sun, Jun 8 | Porter Airlines£10518% OFF£128 £105
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YTO 13:0017h 25m1 stopsCHI Invalid DateToronto - Chicago | Sun, Apr 27 | Normal AirlineCHI 15:006hDirectYTO 16:00Chicago - Toronto | Tue, Apr 29 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopYTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Sun, May 25 | Porter Airlines£65 £11142% OFF42% OFF£111 £65
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Fri, Jun 6 | Porter Airlines£67 £11139% OFF39% OFF£111 £67
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YTZ 16:051h 49mDirectMDW 16:54Toronto - Chicago | Wed, May 28 | Porter Airlines£67 £11139% OFF39% OFF£111 £67
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Mon, Jun 9 | Porter Airlines£6739% OFF£111 £67
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Tue, May 27 | Porter Airlines£6739% OFF£111 £67
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Tue, May 20 | Porter Airlines£6739% OFF£111 £67
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YTZ 15:351h 49mDirectMDW 16:24Toronto - Chicago | Tue, Jun 3 | Porter Airlines£6839% OFF£111 £68
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Mon, May 26 | Porter Airlines£6839% OFF£111 £68
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Sat, May 24 | Porter Airlines£6839% OFF£111 £68
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YTZ 16:051h 49mDirectMDW 16:54Toronto - Chicago | Fri, May 30 | Porter Airlines£9118% OFF£111 £91
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YTO 13:0017h 25m1 stopsCHI Invalid DateToronto - Chicago | Sun, Apr 27 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Toronto to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
FAQ
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When are flight tickets from Toronto (YTO) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Toronto to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much are flights from Toronto (YTO) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around £187. -
How long is the flight from Toronto (YTO) to Chicago (CHI)?
It takes about 1 hour 59 minutes to fly from Toronto (YTO) to Chicago (CHI). -
What are the most popular airlines that fly from Toronto (YTO) to Chicago (CHI)?
Airlines with flights from Toronto (YTO) to Chicago (CHI): American Airlines, Alaska Airlines, Air Canada, United Airlines, Qantas Airways and Qatar Airways. -
How many airports in Chicago (CHI)?
There are 3 airport(s) in Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.
How to find a cheap flight from Toronto to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Toronto to Chicago. Book your flights at the right time and save more.
Be flexible with your travel dates to get the cheapest flight from Toronto to Chicago.
Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Toronto to Chicago over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Sun, May 25, with one-way flights priced at just £65.
Compare cheap flight deals from Toronto to Chicago across hundreds of airlines.
With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Toronto to Chicago. The cheapest airline for this route is Porter Airlines.
Set up a Price Alert
By setting up a Price Alert for your journey from Toronto to Chicago, you can easily keep an eye on ticket prices without having to check every day.
Don't miss out on cheap flight deals and promo codes from Toronto to Chicago.
You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.
Book early or wait until the last minute.
It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.
Search for flights on the go.
For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Toronto to Chicago and snag some exclusive deals just for you.
Flight Information from Toronto to Chicago
Cheapest one-way flight price | £64 |
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Cheapest return ticket price | £93 |
Off-season travel month | April |
Peak season for travel | January |
Flight distance | 701.97km |
Average flight time | 1 hour 59 minutes |
Popular airline | United Airlines |
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