Flights from Toronto to Chicago, United States

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Did you mean flights from Chicago to Toronto?

Where To Buy Cheap Flights from Toronto to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for 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 found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Toronto to Chicago?

The chart below shows up-to-date information regarding how far in advance to book your flight from Toronto to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $491 $480
7-14 days $430 $435
14-21 days $370 $399
21-30 days $413 $399
30-60 days $391 $391
60-90 days $373 $384
90+ days $390 $390

Compare Flight Prices from Toronto to Chicago by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Toronto to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
April Toronto Chicago !! 21-04-22 21-04-29 0 $370
April Toronto Chicago American 21-04-29 21-05-02 1 $396
May Toronto Chicago Porter 21-05-18 21-05-21 0 $373
June Toronto Chicago Porter 21-06-09 21-06-13 0 $373
July Toronto Chicago Air Canada 21-07-01 21-07-06 0 $391
August Toronto Chicago Air Canada 21-08-20 21-08-24 0 $372
September Toronto Chicago American 21-09-03 21-09-06 1 $390
October Toronto Chicago Porter 21-10-08 21-10-11 0 $370

Cheap Last Minute Flights from Toronto to Chicago

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Toronto to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
14 15 16 17 18 19 20
$485
21 22 23 24 25 26 27
$485 $435
28 29 30 31 1 2 3
$435 $370
4 5 6 7 8 9 10
$370 $390
11 12 13 14 15 16 17
$390
18 19 20 21 22 23 24
$398
25 26 27 28 29 30 1
$398

Connecting Flights vs Direct Flights from Toronto to Chicago

Flights between some cities may be significantly cheaper if you choose 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 $389.

The average price for direct flights from Toronto to Chicago is $370.

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

Weekly Direct Flights from Toronto to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 5 5 5 5 5 5 5 03:16 14:55
United 7 7 7 7 7 4 6 01:00 16:18

One Way Flights vs Round Trip Flights from Toronto to Chicago

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 $214.

The average price for round trip flights from Toronto to Chicago is $370.

Toronto to Chicago Flight Questions

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

Question: How long is the flight from Toronto to Chicago?
Answer: The average Toronto to Chicago flight time is an hour and 51 minutes.
Question: How far is Chicago from Toronto?
Answer: The distance from Toronto to Chicago is 698 kilometers (434 miles).
Question: How common are direct flights from Toronto to Chicago?
Answer: There are 80 direct flights from Toronto to Chicago.
Question: What are the most popular Toronto airlines for direct flights from Toronto to Chicago?
Answer: United Airlines provides 56% of the non-stop flights between Toronto and Chicago.

Airlines in Toronto flying to Chicago Last modified: Apr 19, 2021 15:28 -04:00Number of routes searched: 0Number of itineraries searched: 0

Wondering which airlines fly out of Toronto to Chicago? We've gathered the average price of Toronto airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Toronto to Chicago Airports

These are the major commercial airports we're currently monitoring in Toronto and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Flights from Toronto to Chicago