Air Canada Toronto to Chicago Flights
Cheapflightsplus.com will find cheap Air Canada flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $167 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Air Canada, arrivals and departure details below.
Find Cheap Airfare Toronto (ON) — Chicago (IL) by Air Canada
Cheap Flights from Toronto to Chicago by Air Canada
Price | Departure | Arrival | Flight Time | Airline | Flight |
---|---|---|---|---|---|
from $389 | 5:15 pm Toronto Pearson International | 6:15 pm Chicago O'Hare International | 2h 0m | Air Canada | AC4990 |
from $389 | 1:00 pm Toronto Pearson International | 2:01 pm Chicago O'Hare International | 2h 1m | Air Canada | AC5588 |
from $389 | 2:45 pm Toronto Pearson International | 3:50 pm Chicago O'Hare International | 2h 5m | Air Canada | AC5137 |
from $167 | 10:20 am Toronto Toronto Island | 6:53 pm Chicago O'Hare International | 9h 33m layover 6h 8m - Ottawa | Air Canada | AC7706 AC3553 |
from $238 | 12:25 pm Toronto Toronto Island | 8:16 pm Chicago O'Hare International | 8h 51m layover 4h 57m - Montreal | Air Canada | AC7962 AC8965 |
from $240 | 3:25 pm Toronto Toronto Island | 8:16 pm Chicago O'Hare International | 5h 51m layover 1h 57m - Montreal | Air Canada | AC7968 AC8965 |
from $418 | 2:00 pm Toronto Pearson International | 6:53 pm Chicago O'Hare International | 5h 53m layover 2h 20m - Ottawa | Air Canada | AC456 AC3553 |
from $421 | 11:20 pm Toronto Pearson International | 10:46 pm+1 день Chicago O'Hare International | 24h 26m layover 7h 29m - Montreal 5h 17m - Los Angeles | Air Canada | AC432 AC775 F92446 |
from $519 | 11:20 pm Toronto Pearson International | 10:55 am+2 дня Chicago O'Hare International | 36h 35m layover 18h 34m - Montreal 6h 55m - Mexico City | Air Canada | AC432 AC995 VB186 |
from $548 | 11:20 pm Toronto Pearson International | 11:32 pm+2 дня Chicago O'Hare International | 49h 12m layover 18h 34m - Montreal 19h 35m - Mexico City | Air Canada | AC432 AC995 Y4702 |
from $661 | 11:20 pm Toronto Pearson International | 3:27 pm+2 дня Chicago O'Hare International | 41h 7m layover 8h 19m - Montreal 24h 52m - Orlando | Air Canada | AC432 AC1634 F93043 |
from $726 | 11:20 pm Toronto Pearson International | 9:16 pm+1 день Chicago O'Hare International | 22h 56m layover 8h 19m - Montreal 3h 43m - Punta Cana | Air Canada | AC432 AC1790 F981 |
from $1066 | 11:20 pm Toronto Pearson International | 2:25 pm+2 дня Chicago O'Hare International | 40h 5m layover 18h 34m - Montreal 9h 55m - Mexico City | Air Canada | AC432 AC995 AM686 |
Air Canada Flight Schedule Toronto to Chicago
Departure | Arrival | Flight Details | Flight Time | Price |
---|---|---|---|---|
10:20 am — 6:53 pm
|
10:20 am — 11:17 am
AC7706
Air Canada
Toronto — Ottawa
6h 8m stop
5:25 pm — 6:53 pm
AC3553
Air Canada
Ottawa — Chicago
|
9h 33m including layover |
Find flight
from$167 |
|
11:20 pm — 10:46 pm
+1 day
|
11:20 pm — 0:41 am
AC432
Air Canada
Toronto — Montreal
7h 29m stop
8:05 am — 11:02 am
AC775
Air Canada
Montreal — Los Angeles
5h 17m stop
4:24 pm — 10:46 pm
F92446
Frontier Airlines
Los Angeles — Chicago
|
24h 26m including layover |
Find flight
from$421 |
|
11:20 pm — 10:55 am
+2 days
|
11:20 pm — 0:41 am
AC432
Air Canada
Toronto — Montreal
18h 34m stop
7:15 pm — 10:55 pm
AC995
Air Canada
Montreal — Mexico City
6h 55m stop
5:50 am — 10:55 am
VB186
VivaAerobus
Mexico City — Chicago
|
36h 35m including layover |
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from$519 |
|
11:20 pm — 11:32 pm
+2 days
|
11:20 pm — 0:41 am
AC432
Air Canada
Toronto — Montreal
18h 34m stop
7:15 pm — 10:55 pm
AC995
Air Canada
Montreal — Mexico City
19h 35m stop
6:30 pm — 11:32 pm
Y4702
Volaris
Mexico City — Chicago
|
49h 12m including layover |
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from$548 |
|
11:20 pm — 3:27 pm
+2 days
|
11:20 pm — 0:41 am
AC432
Air Canada
Toronto — Montreal
8h 19m stop
9:00 am — 12:14 pm
AC1634
Air Canada
Montreal — Orlando
24h 52m stop
1:06 pm — 3:27 pm
F93043
Frontier Airlines
Orlando — Chicago
|
41h 7m including layover |
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from$661 |
|
11:20 pm — 9:16 pm
+1 day
|
11:20 pm — 0:41 am
AC432
Air Canada
Toronto — Montreal
8h 19m stop
9:00 am — 1:25 pm
AC1790
Air Canada
Montreal — Punta Cana
3h 43m stop
5:08 pm — 9:16 pm
F981
Frontier Airlines
Punta Cana — Chicago
|
22h 56m including layover |
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from$726 |
|
11:20 pm — 2:25 pm
+2 days
|
11:20 pm — 0:41 am
AC432
Air Canada
Toronto — Montreal
18h 34m stop
7:15 pm — 10:55 pm
AC995
Air Canada
Montreal — Mexico City
9h 55m stop
8:50 am — 2:25 pm
AM686
Aeromexico
Mexico City — Chicago
|
40h 5m including layover |
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from$1066 |
|
12:25 pm — 8:16 pm
|
12:25 pm — 1:43 pm
AC7962
Air Canada
Toronto — Montreal
4h 57m stop
6:40 pm — 8:16 pm
AC8965
Air Canada
Montreal — Chicago
|
8h 51m including layover |
Find flight
from$238 |
|
1:00 pm — 2:01 pm
|
1:00 pm — 2:01 pm
AC5588
Air Canada
Toronto — Chicago
|
2h 1m |
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from$389 |
|
2:00 pm — 6:53 pm
|
2:00 pm — 3:05 pm
AC456
Air Canada
Toronto — Ottawa
2h 20m stop
5:25 pm — 6:53 pm
AC3553
Air Canada
Ottawa — Chicago
|
5h 53m including layover |
Find flight
from$418 |
|
2:45 pm — 3:50 pm
|
2:45 pm — 3:50 pm
AC5137
Air Canada
Toronto — Chicago
|
2h 5m |
Find flight
from$389 |
|
3:25 pm — 8:16 pm
|
3:25 pm — 4:43 pm
AC7968
Air Canada
Toronto — Montreal
1h 57m stop
6:40 pm — 8:16 pm
AC8965
Air Canada
Montreal — Chicago
|
5h 51m including layover |
Find flight
from$240 |
|
5:15 pm — 6:15 pm
|
5:15 pm — 6:15 pm
AC4990
Air Canada
Toronto — Chicago
|
2h |
Find flight
from$389 |
Flight Information
There are 3 flights by Air Canada 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 10:20 am to 5:15 pm. Nonstop flight is 2h. The time difference between Toronto and Chicago is 1h.
- The fastest flight 2h
- Average flight time 2h 1m
- The earliest flight 10:20 am
- The latest flight 5:15 pm
- Distance 436 ml
The cheapest months for traveling to Chicago are june (from 147 $), august (from 167 $), may (from 207 $).
The most expensive and popular months are november (from 879 $), july (from 389 $), may (from 207 $).
The cheapest flight by Air Canada that our users were able to find is $167. This airfare is economy class on one-way AC7706 flight for August 15, 2025 leaving Toronto Island in Toronto at 10:20 am, it includes all taxes and additional fees.
Air Canada Airplanes on the Route
List of the most popular Air Canada airplanes flying from Toronto to Chicago:
- Embraer 175from $389Find
Other Popular Airlines on the Route
Besides Air Canada there are other 9 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 27 direct flights every day from Toronto. Airlines and fares are below:
- from $75Find
- from $98Find
- TS - Air Transatfrom $119Find
Connecting Flights
List of flights with layovers (1 and more stops):
- from $175Find
- from $114Find
- F8 - Freedom Airlinesfrom $163Find
- AV - Aviancafrom $602Find
- SY - Sun Country Airlinesfrom $219Find
- WS - WestJetfrom $188Find
- AM - Aeromexicofrom $674Find
- LX - SWISS International Air Linesfrom $4268Find
- TS - Air Transatfrom $198Find
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