Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Flights
Hotels
1 traveler
Unsupported Browser!
Find Flights

Cheap Flights from Toronto to Chicago, IL, United States - YTO to CHI

Popular flights from Toronto to Chicago

If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.

Air Canada
Departure Date Return Date Lowest Price
Mar 21, 2016 Mar 25, 2016 CAD271
Mar 23, 2016 Mar 29, 2016 CAD271
Apr 13, 2016 Apr 19, 2016 CAD271
American Airlines
Departure Date Return Date Lowest Price
Mar 5, 2016 Mar 9, 2016 CAD270
Mar 6, 2016 Mar 8, 2016 CAD270
Mar 7, 2016 Mar 10, 2016 CAD270
Mar 16, 2016 Mar 23, 2016 CAD270
Mar 21, 2016 Mar 25, 2016 CAD270
JetBlue Airways
Departure Date Return Date Lowest Price
Mar 24, 2016 Mar 27, 2016 CAD476
Porter Airlines
Departure Date Return Date Lowest Price
Mar 3, 2016 Mar 4, 2016 CAD268
Mar 3, 2016 Mar 9, 2016 CAD268
Mar 4, 2016 Mar 7, 2016 CAD268
Mar 4, 2016 Mar 12, 2016 CAD268
Mar 4, 2016 Mar 16, 2016 CAD268
Spirit Airlines
Departure Date Return Date Lowest Price
Mar 26, 2016 Mar 28, 2016 CAD551
United Airlines
Departure Date Return Date Lowest Price
Mar 4, 2016 Mar 7, 2016 CAD277
Mar 4, 2016 Mar 12, 2016 CAD277
Mar 6, 2016 Mar 8, 2016 CAD277
Mar 6, 2016 Mar 9, 2016 CAD277
Mar 7, 2016 Mar 10, 2016 CAD277
WestJet
Departure Date Return Date Lowest Price
Feb 26, 2016 Mar 6, 2016 CAD459

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 CAD268.

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 CAD422 CAD533
7-14 days CAD369 CAD381
14-21 days CAD268 CAD286
21-30 days CAD268 CAD279
30-60 days CAD268 CAD274
60-90 days CAD268 CAD279
90+ days CAD268 CAD286

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
CAD268 CAD268 CAD268 CAD268 CAD268 CAD268 CAD268

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
February Toronto Chicago Porter 2/25/16 3/3/16 0 CAD369
March Toronto Chicago Porter 3/3/16 3/4/16 0 CAD268
April Toronto Chicago Porter 4/2/16 4/4/16 0 CAD268
May Toronto Chicago Porter 5/4/16 5/7/16 0 CAD268
June Toronto Chicago Porter 6/3/16 6/5/16 0 CAD268
July Toronto Chicago American 7/21/16 7/23/16 1 CAD296
August Toronto Chicago American 8/18/16 9/7/16 1 CAD296
September Toronto Chicago American 9/26/16 9/29/16 1 CAD299

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
14 15 16 17 18 19 20
CAD818
21 22 23 24 25 26 27
CAD818 CAD454
28 29 1 2 3 4 5
CAD454 CAD268
6 7 8 9 10 11 12
CAD268 CAD268
13 14 15 16 17 18 19
CAD268 CAD268
20 21 22 23 24 25 26
CAD268

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 CAD385.

The average price for non-stop flights from Toronto to Chicago is CAD309.

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 7 7 7 7 7 5 7 06:35 19:43
Air Canada 7 7 7 7 7 5 6 07:25 20:40
Porter 5 5 5 5 5 2 4 07:00 19:55
United 5 5 5 5 5 4 5 06:51 17:21

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 CAD197.

The average price for round trip flights from Toronto to Chicago is CAD367.

More Cheap Flights

FlightsAirlineLowest Price
Cleveland to Chicago American, United CAD264
Buffalo to Chicago American, United CAD302
Syracuse to Chicago American, United CAD371
Rochester to Chicago American, United CAD317
London to Chicago American, Air Canada, United, WestJet CAD324
Binghamton to Chicago American, United CAD491
Elmira - Corning to Chicago American, United CAD498
Erie to Chicago United CAD398
Ithaca to Chicago American, United CAD477
Kingston to Chicago Air Canada, United CAD708
Toronto to New York American, Air Canada, Alaska, JetBlue, Porter, United, WestJet CAD219
Toronto to Milwaukee American, Air Canada, JetBlue, Frontier, United, WestJet CAD434
Cleveland to Milwaukee American, United CAD547
Buffalo to New York American, JetBlue CAD158
Buffalo to Atlanta American, United CAD388
Cleveland to Atlanta American, Frontier, Spirit, United CAD132
Toronto to Atlanta American, Air Canada, Alaska, Frontier, Spirit, Porter, United, WestJet CAD408
Cleveland to New York American, JetBlue, United CAD292
Buffalo to Milwaukee American, United CAD448
Toronto to Detroit American, Air Canada, JetBlue, Spirit, Porter, United, WestJet CAD423
Rochester to Atlanta American, United CAD402
Rochester to Milwaukee American, United CAD366
Cleveland to Dallas - Ft Worth American, Spirit, United CAD109
Toronto to Dallas - Ft Worth American, Air Canada, Alaska, JetBlue, Spirit, Porter, Sun Country, United, WestJet CAD358
Toronto to St Louis American, Air Canada, Frontier, United, WestJet CAD374
Toronto to Washington American, Air Canada, JetBlue, Porter, Sun Country, United, WestJet CAD231
Buffalo to Dallas - Ft Worth American, JetBlue, United CAD323
Toronto to South Bend Air Canada, United, WestJet CAD551
Syracuse to Milwaukee American, United CAD358

Airlines Flying from Toronto to Chicago (YTO to CHI)

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 JFK X X X X X X X
Air Canada - X X X X X X X
Delta DTW X X X X X X X
Porter - X X X X X X X
United - 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 54 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 158 direct flights from Toronto to Chicago.
Question: What is the most popular airline for non-stop flights from Toronto to Chicago?
Answer: American Airlines provides 29% of the non-stop flights between Toronto and Chicago.
Question: What are the most popular connecting cities when flying from Toronto to Chicago?
Answer: Atlanta, GA
Toronto (YTO) To Chicago, IL (CHI) Flights: Cheap Flights From Toronto To Chicago | FareCompare.