Cheap Flights from Toronto, ON to Chicago, IL from $79

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On Cheapflightsplus.com you will find 9 direct and 116 connecting flights from Toronto to Chicago. You can compare airfare deals from 9 airlines and multiple travel sites from $79, book and save on cheap plane tickets and last minute offers. Also check out YTO-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Toronto to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $79 (one-way), $135 (round-trip).

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Best Flights from Toronto to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Toronto to Chicago with the lowest price of $79. The fastest direct flight takes 1h 49m and the fastest connecting – 4h 6m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $79 Find flight	15:35 Toronto Toronto Island	16:24 Chicago Midway	1h 49m	Porter Airlines	PD2393
from $93 Find flight	14:10 Toronto Pearson International	15:04 Chicago O'Hare International	1h 54m	United Airlines	UA8307
from $113 Find flight	17:15 Toronto Pearson International	18:15 Chicago O'Hare International	2h 0m	United Airlines	UA1371
from $107 Find flight	21:10 Toronto Pearson International	07:38+1 день Chicago O'Hare International	11h 28m layover 7h 12m - Newark	United Airlines	UA8266 UA2164
from $129 Find flight	08:10 Toronto Pearson International	14:33 Chicago O'Hare International	7h 23m layover 3h 43m - Washington D.C.	United Airlines	UA8271 UA2331

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 18, 2025

Flight Schedule Toronto (Ontario) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Toronto to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
07:15 — 20:00	07:15 — 08:55 PD603 Porter Airlines Toronto — New York 9h 35m stop 18:30 — 20:00 NK1179 Spirit Airlines New York — Chicago	13h 45m including layover	Find flight from$192
08:10 — 14:33	08:10 — 09:39 UA8271 United Airlines Toronto — Washington D.C. 3h 43m stop 13:20 — 14:33 UA2331 United Airlines Washington D.C. — Chicago	7h 23m including layover	Find flight from$129
09:45 — 20:00	09:45 — 11:15 PD2127 Porter Airlines Toronto — New York 7h 15m stop 18:30 — 20:00 NK1179 Spirit Airlines New York — Chicago	11h 15m including layover	Find flight from$196
11:00 — 12:01	11:00 — 12:01 UA3499 United Airlines Toronto — Chicago	2h 1m	Find flight from$197
12:15 — 16:52	12:10 — 13:41 UA8670 United Airlines Toronto — Washington D.C. 1h 57m stop 15:35 — 16:48 UA1057 United Airlines Washington D.C. — Chicago	5h 37m including layover	Find flight from$122
12:20 — 13:13	12:20 — 13:13 UA8694 United Airlines Toronto — Chicago	1h 53m	Find flight from$120
13:00 — 14:01	13:00 — 14:01 UA3605 United Airlines Toronto — Chicago	2h 1m	Find flight from$93
14:10 — 15:04	14:10 — 15:04 UA8307 United Airlines Toronto — Chicago	1h 54m	Find flight from$93
14:50 — 20:00	14:50 — 16:30 PD605 Porter Airlines Toronto — New York 2h stop 18:30 — 20:00 NK1179 Spirit Airlines New York — Chicago	6h 10m including layover	Find flight from$192
15:35 — 16:24	15:35 — 16:24 PD2393 Porter Airlines Toronto — Chicago	1h 49m	Find flight from$79
15:35 — 16:24	15:35 — 16:24 TS7314 Air Transat Toronto — Chicago	1h 49m	Find flight from$119
17:15 — 18:15	17:15 — 18:15 UA1371 United Airlines Toronto — Chicago	2h	Find flight from$113
18:35 — 19:29	18:35 — 19:29 UA8293 United Airlines Toronto — Chicago	1h 54m	Find flight from$93
21:00 — 22:05	21:00 — 22:05 UA3640 United Airlines Toronto — Chicago	2h 5m	Find flight from$120
21:10 — 07:38 +1 day	21:10 — 22:47 UA8266 United Airlines Toronto — Newark 7h 12m stop 06:00 — 07:38 UA2164 United Airlines Newark — Chicago	11h 28m including layover	Find flight from$107

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on September 18, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Toronto to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Toronto and Chicago is 701 miles. Time difference between the cities is 1h. Airplanes depart 00:30 to 23:50 from 3 Toronto airports and arrive 00:30 to 23:50 to 7 Chicago airports. Average flight time is 1h 54m.

The fastest flight 1h 49m
Average flight time 1h 54m
The earliest flight 00:30
The latest flight 23:50
Distance 436 ml

The cheapest months to travel to Chicago are october (from 79 $), september (from 93 $), july (from 97 $).

The most expensive months are february (from 211 $), january (from 196 $), november (from 172 $).

What is the lowest airfare Toronto to Chicago?

The cheapest plane ticket found by our users is $79. This airfare is for economy class on one-way PD2393 flight by Porter Airlines for October 7, 2025 which leaves Toronto Island in Toronto at 15:35 am and arrives at Chicago Midway at 16:24.

Economy class

$79

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Business class

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First class

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Popular Airlines on the Route

The flight Toronto — Chicago is served by 9 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Air Canada - 6 departures per week at the price of from $ 487 . And the most expensive tickets are offered by Finnair airline - from $ 3290.

Direct flights

There are 9 nonstop flights on the route. The fastest direct flight is PD2393 by Porter Airlines takes 1h 49m and the cheapest is PD2393 by Porter Airlines for $79.

PD - Porter Airlines

from $79

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UA - United Airlines

from $93

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TS - Air Transat

from $119

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Connecting Flights

There are 116 flights with layovers on the route. The fastest connecting flight is AC7704 by Air Canada takes 4h 6m and the cheapest is PD2393 by Porter Airlines for $107.

F8 - Freedom Airlines

from $213

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AC - Air Canada

from $487

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PD - Porter Airlines

from $192

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AV - Avianca

from $1065

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SY - Sun Country Airlines

from $334

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AY - Finnair

from $3260

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UA - United Airlines

from $107

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WS - WestJet

from $225

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TS - Air Transat

from $221

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Airports

You can fly from Toronto to Chicago from 3 airports (Buttonville Municipal, Toronto Island, Pearson International).

Toronto airports

Buttonville Municipal-YKZ

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Toronto Island-YTZ

from $79
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Pearson International-YYZ

from $93
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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Toronto by 9 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top International Destinations from Toronto

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Toronto — Ontario

from $75

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Toronto — Miami

from $55

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Toronto — Orlando

from $64

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Toronto — New York

from $54

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Toronto — Las Vegas

from $72

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Toronto — Boston

from $78

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Toronto — Chicago

from $73

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Toronto — Los Angeles

from $65

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Toronto — Nashville

from $56

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Toronto — Tampa

from $66

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
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That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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