United Airlines Toronto to Chicago Flights

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Cheapflightsplus.com will find cheap United Airlines flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $95 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of United Airlines, arrivals and departure details below.

Find Cheap Airfare Toronto (ON) — Chicago (IL) by United Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in september: one-way - $95, two-way – $163.

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Cheap Flights from Toronto to Chicago by United Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by United Airlines, their prices start from $95. The fastest nonstop flight takes 1h 53m. The fastest connecting flight — 4h 43m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $95 Find flight	2:10 pm Toronto Pearson International	3:04 pm Chicago O'Hare International	1h 54m	United Airlines	UA8307
from $95 Find flight	1:00 pm Toronto Pearson International	2:01 pm Chicago O'Hare International	2h 1m	United Airlines	UA3605
from $95 Find flight	6:35 pm Toronto Pearson International	7:29 pm Chicago O'Hare International	1h 54m	United Airlines	UA8293
from $116 Find flight	5:15 pm Toronto Pearson International	6:15 pm Chicago O'Hare International	2h 0m	United Airlines	UA1371
from $123 Find flight	9:00 pm Toronto Pearson International	10:05 pm Chicago O'Hare International	2h 5m	United Airlines	UA3640
from $123 Find flight	12:20 pm Toronto Pearson International	1:13 pm Chicago O'Hare International	1h 53m	United Airlines	UA8694
from $203 Find flight	11:00 am Toronto Pearson International	12:01 pm Chicago O'Hare International	2h 1m	United Airlines	UA3499
from $110 Find flight	9:10 pm Toronto Pearson International	7:38 am+1 день Chicago O'Hare International	11h 28m layover 7h 12m - Newark	United Airlines	UA8266 UA2164
from $126 Find flight	12:15 pm Toronto Pearson International	4:52 pm Chicago O'Hare International	5h 37m layover 1h 57m - Washington D.C.	United Airlines	UA8670 UA1057
from $132 Find flight	8:10 am Toronto Pearson International	2:33 pm Chicago O'Hare International	7h 23m layover 3h 43m - Washington D.C.	United Airlines	UA8271 UA2331
from $246 Find flight	2:00 pm Toronto Pearson International	6:53 pm Chicago O'Hare International	5h 53m layover 2h 20m - Ottawa	United Airlines	UA8450 UA3659
from $409 Find flight	12:45 pm Toronto Pearson International	6:40 pm Chicago O'Hare International	6h 55m layover 2h 54m - Washington D.C.	United Airlines	UA3633 UA2497
from $409 Find flight	12:45 pm Toronto Pearson International	4:52 pm Chicago O'Hare International	5h 7m layover 1h 20m - Washington D.C.	United Airlines	UA3633 UA1057
from $427 Find flight	8:35 am Toronto Pearson International	9:36 pm Chicago O'Hare International	14h 1m layover 9h 42m - Newark	United Airlines	UA8656 UA353
from $427 Find flight	11:25 am Toronto Pearson International	7:57 pm Chicago O'Hare International	9h 32m layover 5h 13m - Newark	United Airlines	UA8664 UA254
from $427 Find flight	1:55 pm Toronto Pearson International	9:36 pm Chicago O'Hare International	8h 41m layover 4h 22m - Newark	United Airlines	UA8660 UA353

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 09/07/2025

United Airlines Flight Schedule Toronto to Chicago

Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.

Departure	Flight Details	Flight Time	Price
11:00 am — 12:01 pm	11:00 am — 12:01 pm UA3499 United Airlines Toronto — Chicago	2h 1m	Find flight from$203
12:20 pm — 1:13 pm	12:20 pm — 1:13 pm UA8694 United Airlines Toronto — Chicago	1h 53m	Find flight from$123
1:00 pm — 2:01 pm	1:00 pm — 2:01 pm UA3605 United Airlines Toronto — Chicago	2h 1m	Find flight from$95
2:10 pm — 3:04 pm	2:10 pm — 3:04 pm UA8307 United Airlines Toronto — Chicago	1h 54m	Find flight from$95
5:15 pm — 6:15 pm	5:15 pm — 6:15 pm UA1371 United Airlines Toronto — Chicago	2h	Find flight from$116
6:35 pm — 7:29 pm	6:35 pm — 7:29 pm UA8293 United Airlines Toronto — Chicago	1h 54m	Find flight from$95
9:00 pm — 10:05 pm	9:00 pm — 10:05 pm UA3640 United Airlines Toronto — Chicago	2h 5m	Find flight from$123
10:45 am — 2:55 pm	10:45 am — 12:23 pm UA3648 United Airlines Toronto — Newark 55m stop 1:18 pm — 2:55 pm UA2180 United Airlines Newark — Chicago	5h 10m including layover	Find flight from$694
11:25 am — 7:57 pm	11:25 am — 1:02 pm UA8664 United Airlines Toronto — Newark 5h 13m stop 6:15 pm — 7:57 pm UA254 United Airlines Newark — Chicago	9h 32m including layover	Find flight from$427
12:15 pm — 4:52 pm	12:10 pm — 1:41 pm UA8670 United Airlines Toronto — Washington D.C. 1h 57m stop 3:35 pm — 4:48 pm UA1057 United Airlines Washington D.C. — Chicago	5h 37m including layover	Find flight from$126
1:55 pm — 9:36 pm	1:55 pm — 3:32 pm UA8660 United Airlines Toronto — Newark 4h 22m stop 7:54 pm — 9:36 pm UA353 United Airlines Newark — Chicago	8h 41m including layover	Find flight from$427
2:00 pm — 6:53 pm	2:00 pm — 3:04 pm UA8450 United Airlines Toronto — Ottawa 2h 20m stop 5:25 pm — 6:53 pm UA3659 United Airlines Ottawa — Chicago	5h 53m including layover	Find flight from$246
5:30 pm — 7:38 am +1 day	5:30 pm — 7:05 pm UA8202 United Airlines Toronto — Newark 10h 55m stop 6:00 am — 7:38 am UA2160 United Airlines Newark — Chicago	15h 8m including layover	Find flight from$427
7:30 am — 2:55 pm	7:30 am — 9:04 am UA3435 United Airlines Toronto — Newark 4h 14m stop 1:18 pm — 2:55 pm UA2180 United Airlines Newark — Chicago	8h 25m including layover	Find flight from$474
7:47 pm — 7:49 am +1 day	7:47 pm — 9:25 pm UA3466 United Airlines Toronto — Washington D.C. 9h 10m stop 6:35 am — 7:49 am UA708 United Airlines Washington D.C. — Chicago	13h 2m including layover	Find flight from$474
8:10 am — 2:33 pm	8:10 am — 9:39 am UA8271 United Airlines Toronto — Washington D.C. 3h 43m stop 1:20 pm — 2:33 pm UA2331 United Airlines Washington D.C. — Chicago	7h 23m including layover	Find flight from$132
8:35 am — 9:36 pm	8:35 am — 10:12 am UA8656 United Airlines Toronto — Newark 9h 42m stop 7:54 pm — 9:36 pm UA353 United Airlines Newark — Chicago	14h 1m including layover	Find flight from$427
9:10 pm — 7:38 am +1 day	9:10 pm — 10:47 pm UA8266 United Airlines Toronto — Newark 7h 12m stop 6:00 am — 7:38 am UA2164 United Airlines Newark — Chicago	11h 28m including layover	Find flight from$110

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

*Departure and arrival times are local. Last updated on 09/07/2025

Flight Information

There are 7 flights by United Airlines from Toronto to Chicago every week with departures from Pearson International, Toronto Island, Buttonville Municipal. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:45 am to 9:10 pm. Nonstop flight is 1h 53m. The time difference between Toronto and Chicago is 1h.

The fastest flight 1h 53m
Average flight time 2h
The earliest flight 10:45 am
The latest flight 9:10 pm
Distance 436 ml

The cheapest months for traveling to Chicago are october (from 95 $), september (from 96 $), july (from 116 $).

The most expensive and popular months are november (from 253 $), february (from 217 $), january (from 201 $).

The cheapest flight by United Airlines that our users were able to find is $95. This airfare is economy class on one-way UA8307 flight for October 7, 2025 leaving Pearson International in Toronto at 2:10 pm, it includes all taxes and additional fees.

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United Airlines Airplanes on the Route

List of the most popular United Airlines airplanes flying from Toronto to Chicago:

Other Popular Airlines on the Route

Besides United Airlines there are other 8 airline carriers between Toronto and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Toronto to Chicago.

Nonstop flights

There are 9 direct flights every day from Toronto. Airlines and fares are below:

PD - Porter Airlines

from $81

Find
TS - Air Transat

from $122

Find

See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

AC - Air Canada

from $501

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PD - Porter Airlines

from $198

Find
F8 - Freedom Airlines

from $219

Find
AV - Avianca

from $1095

Find
SY - Sun Country Airlines

from $344

Find
AY - Finnair

from $3353

Find
WS - WestJet

from $231

Find
TS - Air Transat

from $228

Find

See more connecting flights

How to book an air ticket yourself?

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