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

Popular flights from Toronto to Chicago

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
May 29, 2016 Jun 16, 2016 CAD250
May 29, 2016 Jun 15, 2016 CAD250
May 29, 2016 Jun 9, 2016 CAD250
May 29, 2016 Jun 3, 2016 CAD250
May 29, 2016 Jun 1, 2016 CAD250
American Airlines
Departure Date Return Date Lowest Price
May 29, 2016 Jun 9, 2016 CAD266
Jun 21, 2016 Jun 25, 2016 CAD266
Frontier Airlines
Departure Date Return Date Lowest Price
Aug 4, 2016 Aug 7, 2016 CAD608
JetBlue Airways
Departure Date Return Date Lowest Price
May 18, 2016 May 21, 2016 CAD506
Porter Airlines
Departure Date Return Date Lowest Price
Jun 3, 2016 Jun 8, 2016 CAD294
United Airlines
Departure Date Return Date Lowest Price
May 31, 2016 Jun 3, 2016 CAD250
Jun 1, 2016 Jun 7, 2016 CAD250
Jun 3, 2016 Jun 8, 2016 CAD250
Jun 3, 2016 Jun 8, 2016 CAD250
Jun 7, 2016 Jun 9, 2016 CAD250
WestJet
Departure Date Return Date Lowest Price
Jun 1, 2016 Jun 7, 2016 CAD386

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 CAD250.

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 CAD428 CAD428
7-14 days CAD325 CAD340
14-21 days CAD279 CAD286
21-30 days CAD250 CAD266
30-60 days CAD250 CAD260
60-90 days CAD261 CAD270
90+ days CAD261 CAD270

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
CAD256 CAD250 CAD250 CAD250 CAD250 CAD250 CAD250

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
April Toronto Chicago Porter 4/30/16 5/1/16 0 CAD861
May Toronto Chicago Air Canada 5/29/16 5/31/16 0 CAD250
June Toronto Chicago Air Canada 6/1/16 6/7/16 0 CAD250
July Toronto Chicago Air Canada 7/1/16 7/5/16 0 CAD261
August Toronto Chicago Air Canada 8/2/16 8/16/16 0 CAD261
September Toronto Chicago Air Canada 9/2/16 9/6/16 0 CAD261
October Toronto Chicago Air Canada 10/9/16 10/14/16 0 CAD261
November Toronto Chicago American 11/8/16 11/16/16 0 CAD261

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
1 2 3 4 5 6 7
CAD532
8 9 10 11 12 13 14
CAD532 CAD325
15 16 17 18 19 20 21
CAD325 CAD325
22 23 24 25 26 27 28
CAD325 CAD256
29 30 31 1 2 3 4
CAD256 CAD250
5 6 7 8 9 10 11
CAD250

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 CAD365.

The average price for non-stop flights from Toronto to Chicago is CAD306.

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 19:55
Air Canada 7 7 7 7 7 7 7 06:35 20:50
Porter 7 6 6 6 6 4 5 07:00 20:05
United 7 7 7 7 7 3 6 07:00 19:18

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 CAD187.

The average price for round trip flights from Toronto to Chicago is CAD327.

More Cheap Flights

FlightsAirlineLowest Price
Cleveland to Chicago American, United CAD247
Buffalo to Chicago American, United CAD282
Syracuse to Chicago American, United CAD324
Rochester to Chicago American, United CAD322
London to Chicago American, Air Canada, United, WestJet CAD250
Binghamton to Chicago American, United CAD391
Elmira - Corning to Chicago American CAD454
Erie to Chicago United CAD320
Ithaca to Chicago American, United CAD391
Kingston to Chicago Air Canada, United Check Dates
Toronto to New York American, Air Canada, Alaska, JetBlue, Spirit, Porter, Air Transat, United, WestJet, Great Lakes CAD195
Toronto to Milwaukee American, Air Canada, Frontier, Porter, United, WestJet CAD408
Cleveland to Milwaukee American, United CAD484
Buffalo to New York American, JetBlue CAD212
Buffalo to Atlanta American, United CAD352
Cleveland to Atlanta American, Frontier, Spirit, United CAD102
Toronto to Atlanta American, Air Canada, Alaska, Frontier, Spirit, Porter, Air Transat, United, WestJet CAD401
Cleveland to New York American, JetBlue, United CAD322
Buffalo to Milwaukee American, United CAD366
Toronto to Detroit American, Air Canada, JetBlue, Spirit, Porter, United, WestJet, Great Lakes CAD527
Rochester to Atlanta American, JetBlue, United CAD365
Rochester to Milwaukee American, United CAD359
Cleveland to Dallas - Ft Worth American, Spirit, United CAD111
Toronto to Dallas - Ft Worth American, Air Canada, Alaska, JetBlue, Spirit, Porter, Sun Country, United, WestJet CAD329
Toronto to St Louis American, Air Canada, Alaska, JetBlue, Frontier, Porter, United, WestJet CAD429
Toronto to Washington American, Air Canada, Alaska, JetBlue, Porter, United, WestJet, Great Lakes CAD247
Buffalo to Dallas - Ft Worth American, JetBlue, United CAD280
Toronto to South Bend Air Canada, United, WestJet CAD709
Syracuse to Milwaukee American, United CAD434

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 ATL 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 48 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 178 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.