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Cheap flights Toronto to Chicago

1 passenger, economy

Cheap flights Toronto to Chicago

Compare prices, duration and stops

Porter Airlines
PD 2387
14:10
Toronto, Торонто (YTZ)
Sun, 13 sep
1h 50min
Direct
16:00
Chicago, Чикаго-Мидвей (MDW)
Sun, 13 sep
113 $
Passaredo Linhas Aereas
P3 2415
14:50
Toronto, Торонто (YTZ)
Sun, 13 sep
5h 13min
1 stop
20:03
Chicago, Рокфорд (RFD)
Sun, 13 sep
214 $
Passaredo Linhas Aereas
P3 2393
17:45
Toronto, Торонто (YTZ)
Wed, 16 sep
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Wed, 16 sep
114 $
Air Canada
AC 7954
12:30
Toronto, Торонто (YTZ)
Fri, 18 sep
7h 22min
1 stop
19:52
Chicago, О'Хара (ORD)
Fri, 18 sep
182 $
Porter Airlines
PD 2393
17:45
Toronto, Торонто (YTZ)
Sat, 19 sep
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
113 $
Passaredo Linhas Aereas
P3 2393
17:45
Toronto, Торонто (YTZ)
Sat, 19 sep
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
169 $
Porter Airlines
PD 2393
17:45
Toronto, Торонто (YTZ)
Tue, 22 sep
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep
198 $
Air Canada
AC 7956
13:30
Toronto, Торонто (YTZ)
Wed, 23 sep
6h 22min
1 stop
19:52
Chicago, О'Хара (ORD)
Wed, 23 sep
123 $
Passaredo Linhas Aereas
P3 2387
14:10
Toronto, Торонто (YTZ)
Wed, 23 sep
1h 50min
Direct
16:00
Chicago, Чикаго-Мидвей (MDW)
Wed, 23 sep
112 $
Air Canada
AC 7958
14:45
Toronto, Торонто (YTZ)
Thu, 24 sep
5h 7min
1 stop
19:52
Chicago, О'Хара (ORD)
Thu, 24 sep
191 $
Air Canada
AC 7954
12:30
Toronto, Торонто (YTZ)
Fri, 25 sep
7h 22min
1 stop
19:52
Chicago, О'Хара (ORD)
Fri, 25 sep
190 $
Porter Airlines
PD 2387
14:10
Toronto, Торонто (YTZ)
Fri, 25 sep
1h 50min
Direct
16:00
Chicago, Чикаго-Мидвей (MDW)
Fri, 25 sep
111 $
Porter Airlines
PD 2393 Best price
17:45
Toronto, Торонто (YTZ)
Fri, 25 sep
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Fri, 25 sep
110 $
United Airlines
UA 1612
11:00
Toronto, Пирсон (YYZ)
Sun, 27 sep
2h
Direct
13:00
Chicago, О'Хара (ORD)
Sun, 27 sep
121 $
United Airlines
UA 763 🔥 Hot deal
12:50
Toronto, Пирсон (YYZ)
Sun, 27 sep
1h 58min
Direct
14:48
Chicago, О'Хара (ORD)
Sun, 27 sep
121 $
Porter Airlines
PD 2387
14:10
Toronto, Торонто (YTZ)
Sun, 27 sep
1h 50min
Direct
16:00
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep
120 $
Passaredo Linhas Aereas
P3 2387
14:10
Toronto, Торонто (YTZ)
Sun, 27 sep
1h 50min
Direct
16:00
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep
120 $
Porter Airlines
PD 2393
17:45
Toronto, Торонто (YTZ)
Sun, 27 sep
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep
111 $
Air Canada
AC 503
12:05
Toronto, Пирсон (YYZ)
Tue, 29 sep
1h 55min
Direct
14:00
Chicago, О'Хара (ORD)
Tue, 29 sep
117 $
Air Canada
AC 509
18:00
Toronto, Пирсон (YYZ)
Tue, 29 sep
1h 55min
Direct
19:55
Chicago, О'Хара (ORD)
Tue, 29 sep
120 $
Air Canada
AC 511
22:50
Toronto, Пирсон (YYZ)
Tue, 29 sep
1h 58min
Direct
00:48
Chicago, О'Хара (ORD)
Wed, 30 sep +1
120 $
Porter Airlines
PD 2387
14:10
Toronto, Торонто (YTZ)
Fri, 2 oct
1h 50min
Direct
16:00
Chicago, Чикаго-Мидвей (MDW)
Fri, 2 oct
121 $
Passaredo Linhas Aereas
P3 2393
17:45
Toronto, Торонто (YTZ)
Sat, 3 oct
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Sat, 3 oct
111 $
Air Canada
AC 507
16:25
Toronto, Пирсон (YYZ)
Mon, 5 oct
1h 58min
Direct
18:23
Chicago, О'Хара (ORD)
Mon, 5 oct
118 $
Porter Airlines
PD 2393
17:45
Toronto, Торонто (YTZ)
Mon, 5 oct
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Mon, 5 oct
211 $
Porter Airlines
PD 2393
17:45
Toronto, Торонто (YTZ)
Tue, 6 oct
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Tue, 6 oct
122 $
United Airlines
UA 2860
15:00
Toronto, Пирсон (YYZ)
Wed, 7 oct
2h
Direct
17:00
Chicago, О'Хара (ORD)
Wed, 7 oct
123 $
Porter Airlines
PD 2393
17:45
Toronto, Торонто (YTZ)
Wed, 7 oct
1h 50min
Direct
19:35
Chicago, Чикаго-Мидвей (MDW)
Wed, 7 oct
121 $
United Airlines
UA 1612
11:00
Toronto, Пирсон (YYZ)
Fri, 9 oct
2h
Direct
13:00
Chicago, О'Хара (ORD)
Fri, 9 oct
226 $
United Airlines
UA 3637
18:30
Toronto, Пирсон (YYZ)
Fri, 9 oct
10h 2min
1 stop
04:32
Chicago, О'Хара (ORD)
Sat, 10 oct +1
169 $
Air Canada
AC 511
22:50
Toronto, Пирсон (YYZ)
Sat, 10 oct
1h 58min
Direct
00:48
Chicago, О'Хара (ORD)
Sun, 11 oct +1
128 $
Porter Airlines
PD 2387
14:10
Toronto, Торонто (YTZ)
Thu, 15 oct
1h 50min
Direct
16:00
Chicago, Чикаго-Мидвей (MDW)
Thu, 15 oct
121 $
Porter Airlines
PD 2703 🔥 Hot deal
14:05
Toronto, Торонто (YTZ)
Sun, 18 oct
1h 55min
Direct
16:00
Chicago, О'Хара (ORD)
Sun, 18 oct
167 $
Air Canada
AC 507
16:25
Toronto, Пирсон (YYZ)
Thu, 22 oct
1h 58min
Direct
18:23
Chicago, О'Хара (ORD)
Thu, 22 oct
118 $
American Airlines
AA 5045
23:07
Toronto, Пирсон (YYZ)
Sun, 1 nov
6h 54min
1 stop
06:01
Chicago, О'Хара (ORD)
Mon, 2 nov +1
143 $
Porter Airlines
PD 2703
15:10
Toronto, Торонто (YTZ)
Sun, 20 dec
1h 55min
Direct
17:05
Chicago, О'Хара (ORD)
Sun, 20 dec
160 $
Porter Airlines
PD 2705
21:35
Toronto, Торонто (YTZ)
Thu, 7 jan
1h 55min
Direct
23:30
Chicago, О'Хара (ORD)
Thu, 7 jan
175 $
Air Canada
AC 8549
00:20
Toronto, Торонто (YTZ)
Tue, 2 feb
2h 1min
Direct
02:21
Chicago, О'Хара (ORD)
Tue, 2 feb
205 $
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Торонто (YTZ)
Wed, 3 feb
1h 55min
Direct
23:30
Chicago, О'Хара (ORD)
Wed, 3 feb
186 $
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Торонто (YTZ)
Sun, 7 feb
1h 55min
Direct
23:30
Chicago, О'Хара (ORD)
Sun, 7 feb
204 $
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Торонто (YTZ)
Sat, 13 feb
1h 55min
Direct
23:30
Chicago, О'Хара (ORD)
Sat, 13 feb
186 $
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Торонто (YTZ)
Thu, 18 feb
1h 55min
Direct
23:30
Chicago, О'Хара (ORD)
Thu, 18 feb
204 $
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Торонто (YTZ)
Sat, 20 feb
1h 55min
Direct
23:30
Chicago, О'Хара (ORD)
Sat, 20 feb
186 $
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Торонто (YTZ)
Mon, 22 feb
1h 55min
Direct
23:30
Chicago, О'Хара (ORD)
Mon, 22 feb
204 $
Passaredo Linhas Aereas
P3 2703
15:10
Toronto, Торонто (YTZ)
Sat, 27 feb
1h 55min
Direct
17:05
Chicago, О'Хара (ORD)
Sat, 27 feb
186 $

Low price calendar

September 2026
Price chart (September 2026)
min: 114 $ · max: 214 $
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214 $
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Good deal
114 $
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182 $
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169 $
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198 $
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123 $
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191 $
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120 $
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117 $
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Cheap flights Toronto to Chicago

Passaredo Linhas Aereas
Passaredo Linhas Aereas
Mon, Wed, Thu, Sat, Sun
Price from
$111
Air Canada
Air Canada
Mon, Tue, Wed, Thu, Fri, Sat
Price from
$117
Porter Airlines
Porter Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$120
United Airlines
United Airlines
Wed, Fri, Sun
Price from
$121
American Airlines
American Airlines
Sun
Price from
$143

Popular destinations from Toronto

All →
YTO
Toronto — Montreal
Canada → Canada
YMQ
from
$42
YTO
Toronto — Montreal
Canada → Canada
YHU
from
$42
YTO
Toronto — Winnipeg
Canada → Canada
YWG
from
$43
YTO
Toronto — Ottawa
Canada → Canada
YOW
from
$47
YTO
Toronto — Halifax
Canada → Canada
YHZ
from
$51
YTO
Toronto — Regina
Canada → Canada
YQR
from
$60
YTO
Toronto — Montreal
Canada → Canada
YUL
from
$60
YTO
Toronto — Calgary
Canada → Canada
YYC
from
$70
YTO
Toronto — Thunder Bay
Canada → Canada
YQT
from
$70

Popular destinations to Chicago

All →
HOU
Houston — Chicago
United States → United States
CHI
from
$21
NYC
New York — Chicago
United States → United States
CHI
from
$22
PHX
Phoenix — Chicago
United States → United States
CHI
from
$24
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
$26
ATL
Atlanta — Chicago
United States → United States
CHI
from
$27
BNA
Nashville — Chicago
United States → United States
CHI
from
$27
LAX
Los Angeles — Chicago
United States → United States
CHI
from
$31
ORL
Orlando — Chicago
United States → United States
CHI
from
$31
MIA
Miami — Chicago
United States → United States
CHI
from
$32

Cheap flights Toronto to Chicago

Interesting facts about the route

Flight time

1h 55min

Distance

711 km

Average price

$126

Most frequent flight

PD 2393

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

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3 GB

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30

days

$9

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2 GB

data

15

days

$13

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5 GB

data

30

days

$14

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3 GB

data

30

days

$16

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5 GB

data

30

days

$23

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Frequently Asked Questions

The average ticket price Toronto Chicago is $126. The cheapest ticket costs $113, operated by Porter Airlines, flight 2387, departing Toronto on 13 September at 14:10, arriving Chicago on 13 September at 16:00.
The average flight time is 5 hours 13 minutes. The fastest flight takes 1 hour 50 minutes, flight 2387 operated by Porter Airlines, departing Toronto on 13 September at 14:10, arriving Chicago on 13 September at 16:00.
Flights on the Toronto - Chicago route are operated by the following airlines: American Airlines, Air Canada, Passaredo Linhas Aereas, Porter Airlines, United Airlines.
The distance from Toronto to Chicago is 711 km.