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Cheap Flights from Toronto to Chicago, IL, United States - YTO to CHI Last modified: 25-May-2016 1:58 AM

Popular flights from Toronto to Chicago Last modified: 25-May-2016 1:58 AM

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

Air Canada
Departure Date Return Date Lowest Price
10-Jul-2016 14-Jul-2016 $295
28-Jul-2016 2-Aug-2016 $295
31-Aug-2016 13-Sep-2016 $295
2-Sep-2016 9-Sep-2016 $295
Alaska Airlines
Departure Date Return Date Lowest Price
13-Jun-2016 16-Jun-2016 $1,134
American Airlines
Departure Date Return Date Lowest Price
28-Jun-2016 6-Jul-2016 $284
8-Jul-2016 19-Jul-2016 $284
12-Jul-2016 16-Jul-2016 $284
26-Aug-2016 28-Aug-2016 $284
7-Sep-2016 10-Sep-2016 $284
JetBlue Airways
Departure Date Return Date Lowest Price
19-Aug-2016 22-Aug-2016 $447
Porter Airlines
Departure Date Return Date Lowest Price
13-Jul-2016 23-Jul-2016 $264
United Airlines
Departure Date Return Date Lowest Price
16-Jun-2016 19-Jun-2016 $265
WestJet
Departure Date Return Date Lowest Price
11-Jun-2016 17-Jun-2016 $374

How Much Does it Cost to Fly from Toronto to Chicago (YTO to CHI)?

We have collected flight cost data from across the web for travel from Toronto to Chicago, and have found the average flight price for this trip to be $265.

When Can I Buy the Cheapest Flight from Toronto to Chicago (YTO to CHI)?

Airlines can adjust prices for plane tickets from Toronto to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Toronto to Chicago

The chart below shows up-to-date information regarding how far in advance a flight from Toronto to Chicago should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $415 $422
7-14 days $334 $307
14-21 days $265 $302
21-30 days $265 $285
30-60 days $264 $276
60-90 days $265 $284
90+ days $264 $276

Cheapest Day To Fly from Toronto to Chicago

The chart below shows up-to-date information regarding the cheapest days to fly from Toronto to Chicago.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$265 $265 $264 $265 $265 $265 $265

Lowest Fares Chart By Month from Toronto to Chicago

The chart below shows the lowest fare by month when flying from Toronto to Chicago.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Toronto Chicago Porter 30/05/16 08/06/16 0 $415
June Toronto Chicago Porter 14/06/16 20/06/16 0 $265
July Toronto Chicago Porter 13/07/16 23/07/16 0 $264
August Toronto Chicago Porter 06/08/16 08/08/16 0 $265
September Toronto Chicago Porter 01/09/16 07/09/16 0 $265
October Toronto Chicago Porter 04/10/16 07/10/16 0 $265
November Toronto Chicago Air Canada 03/11/16 06/11/16 0 $266
December Toronto Chicago Porter 02/12/16 06/12/16 0 $264

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Toronto to Chicago

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Toronto to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
22 23 24 25 26 27 28
$430
29 30 31 1 2 3 4
$430 $416
5 6 7 8 9 10 11
$416 $332
12 13 14 15 16 17 18
$332 $265
19 20 21 22 23 24 25
$265 $265
26 27 28 29 30 1 2
$265

Non-Stop vs Connecting Flights from Toronto to Chicago (YTO to CHI)

Your Toronto to Chicago flight can be significantly cheaper by choosing a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Toronto to Chicago is $593.

The average price for non-stop flights from Toronto to Chicago is $362.

The chart below shows up to date information regarding non-stop flights from Toronto to Chicago.

Nonstop Flight Details from Toronto to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 8 8 8 8 8 6 8 08:05 19:44
Air Canada 8 8 8 8 8 7 7 06:35 20:50
Porter 7 6 6 7 7 4 5 07:00 20:05
United 7 7 7 7 7 4 6 07:00 19:30

Round Trip vs One Way Flights from Toronto to Chicago (YTO to CHI)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Toronto to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Toronto to Chicago is $403.

The average price for round trip flights from Toronto to Chicago is $565.

More Cheap Flights

FlightsAirlineLowest Price
Cleveland to Chicago American, United $260
Buffalo to Chicago American, United $249
Syracuse to Chicago American, JetBlue, United $380
Rochester to Chicago American, United $316
London to Chicago American, Air Canada, Spirit, Porter, United, WestJet $256
Binghamton to Chicago American, United $432
Elmira - Corning to Chicago American $464
Erie to Chicago United $344
Ithaca to Chicago American, United $510
Kingston to Chicago Air Canada, United Check Dates
Toronto to New York American, Air Canada, Alaska, JetBlue, Porter, United, WestJet, Great Lakes $199
Toronto to Milwaukee American, Air Canada, JetBlue, Frontier, United, WestJet $423
Cleveland to Milwaukee American, United $427
Buffalo to New York American, JetBlue, United $214
Buffalo to Atlanta American, United $320
Cleveland to Atlanta American, Frontier, Spirit, United $141
Toronto to Atlanta American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Porter, United, WestJet $451
Cleveland to New York American, JetBlue, United $222
Buffalo to Milwaukee American, United $444
Toronto to Detroit American, Air Canada, JetBlue, Spirit, Porter, Air Transat, United, WestJet $448
Rochester to Atlanta American, United $373
Rochester to Milwaukee American, United $406
Cleveland to Dallas - Ft Worth American, Spirit, United $151
Toronto to Dallas - Ft Worth American, Air Canada, Alaska, JetBlue, Spirit, Porter, United, WestJet $485
Toronto to St Louis American, Air Canada, Alaska, Frontier, Porter, United, WestJet $409
Toronto to Washington American, Air Canada, Alaska, JetBlue, Spirit, Porter, United, WestJet $253
Buffalo to Dallas - Ft Worth American, JetBlue, United $305
Toronto to South Bend American, Air Canada, JetBlue, Allegiant, United, WestJet $455
Syracuse to Milwaukee American, United $461

Airlines Flying from Toronto to Chicago (YTO to CHI) Number of flights searched: 159Last modified: 25-May-2016 1:58 AM

Below are the different airlines that fly from Toronto to Chicago with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Toronto to Chicago.

Toronto to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American DCA X X X X X X X
Air Canada - X X X X X X X
Delta JFK X X X X X X X
Porter - X X X X X X X
United - X X X X X X X
WestJet YYC X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Toronto and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Toronto to Chicago Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is a direct flight from Toronto to Chicago?
Answer: The average Toronto to Chicago flight time is an hour and 47 minutes.
Question: How many kilometers are there between Toronto and Chicago?
Answer: The distance from Toronto to Chicago is 635 kilometers.
Question: How common are direct flights from Toronto to Chicago?
Answer: There are 193 direct flights from Toronto to Chicago.
Question: What is the most popular airline for non-stop flights from Toronto to Chicago?
Answer: Air Canada provides 27% of the non-stop flights between Toronto and Chicago.
Question: What are the most popular connecting cities when flying from Toronto to Chicago?
Answer: Calgary, AB
Toronto (YTO) To Chicago, IL (CHI) Flights: Cheap Flights From Toronto To Chicago | FareCompare.