Cheap Flights from Toronto, ON to Chicago, IL from $114

One way Round trip

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On Cheapflightsplus.com you will find 10 direct and 138 connecting flights from Toronto to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $114, 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: $114 (one-way), $195 (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 $114. The fastest direct flight takes 1h 50m and the fastest connecting – 3h 45m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $114 Find flight	11:20 Toronto Toronto Island	12:10 Chicago Midway	1h 50m	Porter Airlines	PD2387
from $144 Find flight	11:10 Toronto Toronto Island	12:00 Chicago Midway	1h 50m	Air Transat	TS7060
from $157 Find flight	12:20 Toronto Pearson International	13:11 Chicago O'Hare International	1h 51m	United Airlines	UA8694
from $157 Find flight	14:00 Toronto Pearson International	14:51 Chicago O'Hare International	1h 51m	United Airlines	UA8307
from $181 Find flight	06:52 Toronto Pearson International	08:05 Chicago O'Hare International	2h 13m	United Airlines	UA3534
from $263 Find flight	06:52 Toronto Pearson International	08:01 Chicago O'Hare International	2h 9m	United Airlines	UA5345
from $322 Find flight	09:00 Toronto Pearson International	10:04 Chicago O'Hare International	2h 4m	United Airlines	UA1538
from $136 Find flight	15:00 Toronto Toronto Island	22:55 Chicago O'Hare International	8h 55m layover 4h 45m - New York	Porter Airlines	PD2137 NK225
from $145 Find flight	11:55 Toronto Toronto Island	22:55 Chicago O'Hare International	12h 0m layover 7h 50m - New York	Porter Airlines	PD2131 NK225
from $145 Find flight	09:00 Toronto Toronto Island	22:55 Chicago O'Hare International	14h 55m layover 10h 45m - New York	Porter Airlines	PD2125 NK225
from $147 Find flight	07:15 Toronto Pearson International	15:33 Chicago O'Hare International	9h 18m layover 2h 45m - Fort Myers	Porter Airlines	PD535 NK528
from $147 Find flight	07:15 Toronto Pearson International	17:02 Chicago O'Hare International	10h 47m layover 4h 25m - Fort Myers	Porter Airlines	PD535 NK2930
from $158 Find flight	15:00 Toronto Toronto Island	22:55 Chicago O'Hare International	8h 55m layover 4h 45m - New York	Air Transat	TS7363 NK225
from $159 Find flight	10:00 Toronto Pearson International	22:51 Chicago O'Hare International	13h 51m layover 7h 9m - Miami	Porter Airlines	PD513 NK718
from $150 Find flight	14:00 Toronto Toronto Island	07:18+1 день Chicago O'Hare International	18h 18m layover 4h 35m - New York 6h 0m - Orlando	Porter Airlines	PD2135 NK221 NK1683
from $158 Find flight	20:00 Toronto Pearson International	14:01+1 день Chicago Midway	19h 1m layover 10h 10m - Orlando 0h 48m - Philadelphia	WestJet	WS1166 F92416 F91617

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on January 21, 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
06:52 — 08:05	06:52 — 08:05 UA3534 United Airlines Toronto — Chicago	2h 13m	Find flight from$181
06:52 — 08:01	06:52 — 08:01 UA5345 United Airlines Toronto — Chicago	2h 9m	Find flight from$263
09:00 — 10:04	09:00 — 10:04 UA1538 United Airlines Toronto — Chicago	2h 4m	Find flight from$322
11:00 — 12:09	11:00 — 12:09 UA3556 United Airlines Toronto — Chicago	2h 9m	Find flight from$157
11:10 — 12:00	11:10 — 12:00 TS7060 Air Transat Toronto — Chicago	1h 50m	Find flight from$144
11:20 — 12:10	11:20 — 12:10 PD2387 Porter Airlines Toronto — Chicago	1h 50m	Find flight from$114
12:20 — 13:11	12:20 — 13:11 UA8694 United Airlines Toronto — Chicago	1h 51m	Find flight from$157
14:00 — 14:51	14:00 — 14:51 UA8307 United Airlines Toronto — Chicago	1h 51m	Find flight from$157
18:40 — 19:37	18:40 — 19:37 UA8293 United Airlines Toronto — Chicago	1h 57m	Find flight from$157
21:00 — 22:06	21:00 — 22:06 UA5728 United Airlines Toronto — Chicago	2h 6m	Find flight from$322
07:15 — 15:33	07:15 — 10:35 PD535 Porter Airlines Toronto — Fort Myers 2h 45m stop 13:20 — 15:33 NK528 Spirit Airlines Fort Myers — Chicago	9h 18m including layover	Find flight from$147
07:15 — 17:02	07:15 — 10:35 PD535 Porter Airlines Toronto — Fort Myers 4h 25m stop 15:00 — 17:02 NK2930 Spirit Airlines Fort Myers — Chicago	10h 47m including layover	Find flight from$147
08:35 — 17:02	08:35 — 11:56 WS1236 WestJet Toronto — Fort Myers 3h 4m stop 15:00 — 17:02 NK2930 Spirit Airlines Fort Myers — Chicago	9h 27m including layover	Find flight from$177
09:00 — 22:55	09:00 — 10:30 PD2125 Porter Airlines Toronto — New York 10h 45m stop 21:15 — 22:55 NK225 Spirit Airlines New York — Chicago	14h 55m including layover	Find flight from$145
09:30 — 14:46	09:30 — 11:13 UA3701 United Airlines Toronto — Newark 1h 52m stop 13:05 — 14:46 UA587 United Airlines Newark — Chicago	6h 16m including layover	Find flight from$173
10:00 — 20:13	10:00 — 13:21 PD513 Porter Airlines Toronto — Miami 4h 30m stop 17:50 — 20:13 NK19 Spirit Airlines Miami — Chicago	11h 13m including layover	Find flight from$153
10:00 — 22:51	10:00 — 13:21 PD513 Porter Airlines Toronto — Miami 7h 9m stop 20:30 — 22:51 NK718 Spirit Airlines Miami — Chicago	13h 51m including layover	Find flight from$159
12:20 — 18:38	12:20 — 13:23 UA8288 United Airlines Toronto — Ottawa 3h 37m stop 17:00 — 18:38 UA3659 United Airlines Ottawa — Chicago	7h 18m including layover	Find flight from$162
14:00 — 22:55	14:00 — 15:30 PD2135 Porter Airlines Toronto — New York 5h 45m stop 21:15 — 22:55 NK225 Spirit Airlines New York — Chicago	9h 55m including layover	Find flight from$136
15:00 — 22:55	15:00 — 16:30 PD2137 Porter Airlines Toronto — New York 4h 45m stop 21:15 — 22:55 NK225 Spirit Airlines New York — Chicago	8h 55m including layover	Find flight from$136
15:00 — 22:55	15:00 — 16:30 TS7363 Air Transat Toronto — New York 4h 45m stop 21:15 — 22:55 NK225 Spirit Airlines New York — Chicago	8h 55m including layover	Find flight from$158
16:55 — 10:40 +1 day	16:55 — 20:12 WS1172 WestJet Toronto — Fort Myers 12h 18m stop 08:30 — 10:40 NK570 Spirit Airlines Fort Myers — Chicago	18h 45m including layover	Find flight from$162
16:55 — 15:33 +1 day	16:55 — 20:12 WS1172 WestJet Toronto — Fort Myers 17h 8m stop 13:20 — 15:33 NK528 Spirit Airlines Fort Myers — Chicago	23h 38m including layover	Find flight from$180
19:55 — 13:23 +1 day	19:55 — 23:01 PD527 Porter Airlines Toronto — Tampa 12h 18m stop 11:19 — 13:23 NK716 Spirit Airlines Tampa — Chicago	18h 28m including layover	Find flight from$160
19:55 — 13:43 +1 day	19:55 — 23:01 PD527 Porter Airlines Toronto — Tampa 12h 42m stop 20:04 — 22:04 F91415 Frontier Airlines Tampa — Chicago	18h 48m including layover	Find flight from$161
20:00 — 09:27 +1 day	20:00 — 23:07 WS1166 WestJet Toronto — Orlando 7h 58m stop 07:30 — 09:52 F93043 Frontier Airlines Orlando — Chicago	14h 27m including layover	Find flight from$163
21:00 — 07:40 +1 day	21:00 — 22:37 UA8556 United Airlines Toronto — Washington D.C. 7h 43m stop 06:30 — 07:42 UA1793 United Airlines Washington D.C. — Chicago	11h 40m including layover	Find flight from$187
06:45 — 20:13	06:45 — 08:15 PD2121 Porter Airlines Toronto — New York 3h 40m stop 11:55 — 15:06 NK3930 Spirit Airlines New York — Miami 2h 44m stop 17:50 — 20:13 NK19 Spirit Airlines Miami — Chicago	14h 28m including layover	Find flight from$159
06:45 — 20:13	06:45 — 08:15 PD2121 Porter Airlines Toronto — Newark 2h stop 10:15 — 13:29 NK899 Spirit Airlines Newark — Miami 4h 21m stop 17:50 — 20:13 NK19 Spirit Airlines Miami — Chicago	14h 28m including layover	Find flight from$167
14:00 — 07:18 +1 day	14:00 — 15:30 PD2135 Porter Airlines Toronto — New York 4h 35m stop 20:05 — 23:10 NK221 Spirit Airlines New York — Orlando 6h stop 05:10 — 07:18 NK1683 Spirit Airlines Orlando — Chicago	18h 18m including layover	Find flight from$150
17:00 — 07:18 +1 day	16:25 — 17:55 PD2141 Porter Airlines Toronto — Newark 3h 56m stop 22:26 — 01:16 NK1480 Spirit Airlines Newark — Orlando 3h 54m stop 05:10 — 07:18 NK1683 Spirit Airlines Orlando — Chicago	15h 18m including layover	Find flight from$167
18:20 — 07:18 +1 day	18:20 — 19:50 PD2143 Porter Airlines Toronto — Newark 2h 36m stop 22:26 — 01:16 NK1480 Spirit Airlines Newark — Orlando 3h 54m stop 05:10 — 07:18 NK1683 Spirit Airlines Orlando — Chicago	13h 58m including layover	Find flight from$167
20:00 — 14:01 +1 day	20:00 — 23:07 WS1166 WestJet Toronto — Orlando 10h 10m stop 09:17 — 11:52 F92416 Frontier Airlines Orlando — Philadelphia 48m stop 12:40 — 14:01 F91617 Frontier Airlines Philadelphia — Chicago	19h 1m including layover	Find flight from$158

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

*Departure and arrival times - local. Updated on January 21, 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 06:15 to 23:30 from 3 Toronto airports and arrive 06:15 to 23:30 to 7 Chicago airports. Average flight time is 2h 1m.

The fastest flight 1h 50m
Average flight time 2h 1m
The earliest flight 06:15
The latest flight 23:30
Distance 436 ml

The cheapest months to travel to Chicago are january (from 72 $), february (from 114 $), december (from 121 $).

The most expensive months are november (from 138 $), december (from 121 $), february (from 114 $).

What is the lowest airfare Toronto to Chicago?

The cheapest plane ticket found by our users is $114. This airfare is for economy class on one-way PD2387 flight by Porter Airlines for January 22, 2025 which leaves Toronto Island in Toronto at 11:20 am and arrives at Chicago Midway at 12:10.

Economy class

$114

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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 7 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Air Canada - 1 departures per week at the price of from $ 399 . And the most expensive tickets are offered by Finnair airline - from $ 1412.

Direct flights

There are 10 nonstop flights on the route. The fastest direct flight is PD2387 by Porter Airlines takes 1h 50m and the cheapest is PD2387 by Porter Airlines for $114.

PD - Porter Airlines

from $114

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UA - United Airlines

from $157

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TS - Air Transat

from $144

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Connecting Flights

There are 138 flights with layovers on the route. The fastest connecting flight is WS6342 by WestJet takes 3h 45m and the cheapest is PD2387 by Porter Airlines for $136.

AC - Air Canada

from $399

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PD - Porter Airlines

from $136

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WS - WestJet

from $158

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UA - United Airlines

from $162

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F8 - Freedom Airlines

from $220

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AY - Finnair

from $1296

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TS - Air Transat

from $158

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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 $114
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Pearson International-YYZ

from $147
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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 7 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.

Embraer 175

from $157

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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 — Chicago

from $73

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Toronto — Las Vegas

from $72

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Toronto — New York

from $54

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Toronto — Boston

from $78

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Toronto — Atlanta

from $62

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Toronto — Palm Springs

from $66

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Toronto — Newark

from $73

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Toronto — Los Angeles

from $65

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Toronto — San Francisco

from $64

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Toronto — Honolulu

from $77

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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»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
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.
To find a plane ticket, please select dates.