Flights from Toronto to Chicago, United States

Did you mean flights from Chicago to Toronto?

Toronto to Chicago Last modified: Jan 22, 2024 8:07 -05:00

We've scanned 115,678,683 round trip itineraries and found the cheapest flights to Chicago. Porter & Multiple Airlines frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Porter
YTOCHI
Fri 03-01
nonstop
CHIYTO
Sun 03-03
nonstop
$285
Multiple Airlines
YTOCHI
Sat 02-17
nonstop
CHIYTO
Sun 02-25
nonstop
$292
United
YTOCHI
Sat 02-17
nonstop
CHIYTO
Sun 02-25
nonstop
$292
American
YTOCHI
Wed 02-21
1 stop
CHIYTO
Sat 02-24
1 stop
$306
Air Canada
YTOCHI
Sat 02-10
1 stop
CHIYTO
Sun 02-11
1 stop
$326
Major Airlines
YTOCHI
Fri 02-09
1 stop
CHIYTO
Thu 02-15
1 stop
$326

How Much is a Flight from Toronto to Chicago?

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 $288.

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 $387 $399
7-14 days $296 $307
14-21 days $289 $303
21-30 days $289 $303
30-60 days $285 $303
60-90 days $285 $303
90+ days $289 $303

Cheapest Day To Fly from Toronto to Chicago

We've examined 231,357,366 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Toronto to Chicago is Tuesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$289$285$289$285$289 $289

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
7 8 9 10 11 12 13
$450
14 15 16 17 18 19 20
$450 $300
21 22 23 24 25 26 27
$300 $289
28 29 30 31 1 2 3
$289 $289
4 5 6 7 8 9 10
$289 $289
11 12 13 14 15 16 17
$289

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 $378.

The average price for direct flights from Toronto to Chicago is $369.

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 $215.

The average price for round trip flights from Toronto to Chicago is $369.

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.

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