Cheap Flights from Toronto to Chicago
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Flights from Toronto to Chicago
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.
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 nonstop
YYZ 07:001h 59mDirectORD 07:59Toronto - Chicago | Sun, Aug 3 | United Airlines
ORD 08:501h 59mDirectYYZ 11:49Chicago - Toronto | Wed, Aug 6 | United AirlinesUS$120 US$18134% OFF34% OFFUS$181 US$120 -
YYZ 07:001h 59mDirectORD 07:59Toronto - Chicago | Thu, Jul 24 | United Airlines
ORD 17:551h 49mDirectYYZ 20:44Chicago - Toronto | Wed, Jul 30 | United AirlinesUS$127 US$18130% OFF30% OFFUS$181 US$127
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YYZ 14:101h 54mDirectORD 15:04Toronto - Chicago | Fri, Jul 25 | United Airlines
ORD 18:301h 44mDirectYYZ 21:14Chicago - Toronto | Sun, Jul 27 | United AirlinesUS$131 US$18128% OFF28% OFFUS$181 US$131
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YYZ 09:001h 59mDirectORD 09:59Toronto - Chicago | Fri, Jul 18 | United Airlines
ORD 21:141h 44mDirectYYZ 23:58Chicago - Toronto | Tue, Jul 22 | United AirlinesUS$13327% OFFUS$181 US$133
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YYZ 17:152hDirectORD 18:15Toronto - Chicago | Sat, Jul 26 | United Airlines
ORD 17:551h 49mDirectYYZ 20:44Chicago - Toronto | Sun, Jul 27 | United AirlinesUS$13327% OFFUS$181 US$133
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YYZ 07:001h 59mDirectORD 07:59Toronto - Chicago | Sun, Jun 29 | United Airlines
ORD 14:001h 44mDirectYYZ 16:44Chicago - Toronto | Tue, Jul 1 | United AirlinesUS$13426% OFFUS$181 US$134
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YYZ 08:151h 54mDirectORD 09:09Toronto - Chicago | Sun, Jul 20 | United Airlines
ORD 10:001h 45mDirectYYZ 12:45Chicago - Toronto | Fri, Jul 25 | United AirlinesUS$13525% OFFUS$181 US$135
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YYZ 07:001h 59mDirectORD 07:59Toronto - Chicago | Fri, Jul 4 | United Airlines
ORD 10:001h 45mDirectYYZ 12:45Chicago - Toronto | Sat, Jul 12 | United AirlinesUS$13725% OFFUS$181 US$137
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YYZ 08:151h 54mDirectORD 09:09Toronto - Chicago | Wed, Jul 2 | United Airlines
ORD 14:246h 50m1 stopsYYZ 22:14Chicago - Toronto | Sat, Jul 5 | United AirlinesUS$12928% OFFUS$181 US$129
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YYZ 14:307h 46m1 stopsORD 21:16Toronto - Chicago | Fri, Aug 1 | United Airlines
ORD 14:001h 44mDirectYYZ 16:44Chicago - Toronto | Sun, Aug 3 | United AirlinesUS$14321% OFFUS$181 US$143
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YTO 13:0017h 25m1 stopsCHI Invalid DateToronto - Chicago | Mon, Jun 30 | Normal Airline
CHI 15:006hDirectYTO 16:00Chicago - Toronto | Wed, Jul 2 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
YYZ 21:002h 5mDirectORD 22:05Toronto - Chicago | Fri, Jul 11 | United AirlinesUS$88 US$32873% OFF73% OFFUS$328 US$88
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YTZ 15:351h 49mDirectMDW 16:24Toronto - Chicago | Thu, Aug 14 | Porter AirlinesUS$92 US$32872% OFF72% OFFUS$328 US$92 -
YTZ 15:351h 49mDirectMDW 16:24Toronto - Chicago | Mon, Aug 11 | Porter AirlinesUS$92 US$32872% OFF72% OFFUS$328 US$92
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Tue, Jul 15 | Porter AirlinesUS$9472% OFFUS$328 US$94
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Wed, Jul 30 | Porter AirlinesUS$10070% OFFUS$328 US$100
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Tue, Jul 29 | Porter AirlinesUS$11067% OFFUS$328 US$110
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YTZ 07:551h 50mDirectMDW 08:45Toronto - Chicago | Fri, Aug 15 | Porter AirlinesUS$11465% OFFUS$328 US$114
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YYZ 12:001h 53mDirectORD 12:53Toronto - Chicago | Wed, Jul 23 | United AirlinesUS$17247% OFFUS$328 US$172
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YYZ 07:001h 59mDirectORD 07:59Toronto - Chicago | Sat, Jul 12 | United AirlinesUS$19341% OFFUS$328 US$193
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YYZ 13:002h 1mDirectORD 14:01Toronto - Chicago | Tue, Jul 8 | United AirlinesUS$25921% OFFUS$328 US$259
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YTO 13:0017h 25m1 stopsCHI Invalid DateToronto - Chicago | Mon, Jun 30 | 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.
Flight Information from Toronto to Chicago
| Cheapest one-way flight price | US$88 |
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| Cheapest return ticket price | US$120 |
| Off-season travel month | April |
| Peak season for travel | March |
| Flight distance | 701.97km |
| Average flight time | 1 hour 58 minutes |
| Popular airline | Porter Airlines |
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
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 US$253. -
How long is the flight from Toronto (YTO) to Chicago (CHI)?
It takes about 1 hour 58 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, United Airlines, Air Canada and Iberia. -
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 Fri, Jul 11, with one-way flights priced at just US$88.
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 United 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.
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