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Cheap flights Toronto to Chicago

1 passenger, economy

Cheap flights Toronto to Chicago

Compare prices, duration and stops

Passaredo Linhas Aereas
P3 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Tue, 15 sep
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
299 S$
Passaredo Linhas Aereas
P3 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Wed, 16 sep
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
144 S$
Air Canada
AC 7954
12:30
Toronto, Toronto City Centre Airport (YTZ)
Fri, 18 sep
7h 22min
1 stop
19:52
Chicago, O'Hare International Airport (ORD)
Fri, 18 sep
231 S$
Porter Airlines
PD 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Sat, 19 sep
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
143 S$
Passaredo Linhas Aereas
P3 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Sat, 19 sep
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
214 S$
Passaredo Linhas Aereas
P3 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Mon, 21 sep
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
237 S$
Air Canada
AC 418
20:00
Toronto, Pearson International Airport (YYZ)
Mon, 21 sep
5h 12min
1 stop
01:12
Chicago, O'Hare International Airport (ORD)
Tue, 22 sep +1
240 S$
Porter Airlines
PD 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Tue, 22 sep
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
251 S$
Air Canada
AC 7956
13:30
Toronto, Toronto City Centre Airport (YTZ)
Wed, 23 sep
6h 22min
1 stop
19:52
Chicago, O'Hare International Airport (ORD)
Wed, 23 sep
156 S$
Passaredo Linhas Aereas
P3 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Wed, 23 sep
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
142 S$
Air Canada
AC 7958
14:45
Toronto, Toronto City Centre Airport (YTZ)
Thu, 24 sep
5h 7min
1 stop
19:52
Chicago, O'Hare International Airport (ORD)
Thu, 24 sep
243 S$
Air Canada
AC 7954
12:30
Toronto, Toronto City Centre Airport (YTZ)
Fri, 25 sep
7h 22min
1 stop
19:52
Chicago, O'Hare International Airport (ORD)
Fri, 25 sep
242 S$
Porter Airlines
PD 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Fri, 25 sep
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 sep
140 S$
Porter Airlines
PD 2393 Best price
17:45
Toronto, Toronto City Centre Airport (YTZ)
Fri, 25 sep
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 sep
139 S$
United Airlines
UA 1612
11:00
Toronto, Pearson International Airport (YYZ)
Sun, 27 sep
2h
Direct
13:00
Chicago, O'Hare International Airport (ORD)
Sun, 27 sep
154 S$
United Airlines
UA 763 🔥 Hot deal
12:50
Toronto, Pearson International Airport (YYZ)
Sun, 27 sep
1h 58min
Direct
14:48
Chicago, O'Hare International Airport (ORD)
Sun, 27 sep
154 S$
Porter Airlines
PD 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Sun, 27 sep
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep
152 S$
Passaredo Linhas Aereas
P3 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Sun, 27 sep
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep
153 S$
Porter Airlines
PD 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Sun, 27 sep
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep
140 S$
Air Canada
AC 503
12:05
Toronto, Pearson International Airport (YYZ)
Tue, 29 sep
1h 55min
Direct
14:00
Chicago, O'Hare International Airport (ORD)
Tue, 29 sep
149 S$
Air Canada
AC 509
18:00
Toronto, Pearson International Airport (YYZ)
Tue, 29 sep
1h 55min
Direct
19:55
Chicago, O'Hare International Airport (ORD)
Tue, 29 sep
152 S$
Air Canada
AC 511
22:50
Toronto, Pearson International Airport (YYZ)
Tue, 29 sep
1h 58min
Direct
00:48
Chicago, O'Hare International Airport (ORD)
Wed, 30 sep +1
153 S$
Porter Airlines
PD 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Fri, 2 oct
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Fri, 2 oct
154 S$
Passaredo Linhas Aereas
P3 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Sat, 3 oct
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
141 S$
Air Canada
AC 507
16:25
Toronto, Pearson International Airport (YYZ)
Mon, 5 oct
1h 58min
Direct
18:23
Chicago, O'Hare International Airport (ORD)
Mon, 5 oct
149 S$
Porter Airlines
PD 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Mon, 5 oct
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Mon, 5 oct
268 S$
Porter Airlines
PD 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Tue, 6 oct
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct
155 S$
United Airlines
UA 2860
15:00
Toronto, Pearson International Airport (YYZ)
Wed, 7 oct
2h
Direct
17:00
Chicago, O'Hare International Airport (ORD)
Wed, 7 oct
156 S$
Porter Airlines
PD 2393
17:45
Toronto, Toronto City Centre Airport (YTZ)
Wed, 7 oct
1h 50min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
154 S$
United Airlines
UA 1612
11:00
Toronto, Pearson International Airport (YYZ)
Fri, 9 oct
2h
Direct
13:00
Chicago, O'Hare International Airport (ORD)
Fri, 9 oct
287 S$
United Airlines
UA 3637
18:30
Toronto, Pearson International Airport (YYZ)
Fri, 9 oct
10h 2min
1 stop
04:32
Chicago, O'Hare International Airport (ORD)
Sat, 10 oct +1
215 S$
Air Canada
AC 511
22:50
Toronto, Pearson International Airport (YYZ)
Sat, 10 oct
1h 58min
Direct
00:48
Chicago, O'Hare International Airport (ORD)
Sun, 11 oct +1
163 S$
Porter Airlines
PD 2387
14:10
Toronto, Toronto City Centre Airport (YTZ)
Thu, 15 oct
1h 50min
Direct
16:00
Chicago, Chicago Midway International Airport (MDW)
Thu, 15 oct
154 S$
Porter Airlines
PD 2703 🔥 Hot deal
14:05
Toronto, Toronto City Centre Airport (YTZ)
Sun, 18 oct
1h 55min
Direct
16:00
Chicago, O'Hare International Airport (ORD)
Sun, 18 oct
212 S$
Air Canada
AC 507
16:25
Toronto, Pearson International Airport (YYZ)
Thu, 22 oct
1h 58min
Direct
18:23
Chicago, O'Hare International Airport (ORD)
Thu, 22 oct
149 S$
American Airlines
AA 5045
23:07
Toronto, Pearson International Airport (YYZ)
Sun, 1 nov
6h 54min
1 stop
06:01
Chicago, O'Hare International Airport (ORD)
Mon, 2 nov +1
182 S$
Porter Airlines
PD 2703
15:35
Toronto, Toronto City Centre Airport (YTZ)
Sun, 15 nov
2h 5min
Direct
17:40
Chicago, O'Hare International Airport (ORD)
Sun, 15 nov
162 S$
Porter Airlines
PD 2703
15:10
Toronto, Toronto City Centre Airport (YTZ)
Sun, 20 dec
1h 55min
Direct
17:05
Chicago, O'Hare International Airport (ORD)
Sun, 20 dec
203 S$
Porter Airlines
PD 2705
21:35
Toronto, Toronto City Centre Airport (YTZ)
Thu, 7 jan
1h 55min
Direct
23:30
Chicago, O'Hare International Airport (ORD)
Thu, 7 jan
222 S$
Air Canada
AC 8549
00:20
Toronto, Toronto City Centre Airport (YTZ)
Tue, 2 feb
2h 1min
Direct
02:21
Chicago, O'Hare International Airport (ORD)
Tue, 2 feb
260 S$
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Toronto City Centre Airport (YTZ)
Wed, 3 feb
1h 55min
Direct
23:30
Chicago, O'Hare International Airport (ORD)
Wed, 3 feb
236 S$
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Toronto City Centre Airport (YTZ)
Sun, 7 feb
1h 55min
Direct
23:30
Chicago, O'Hare International Airport (ORD)
Sun, 7 feb
258 S$
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Toronto City Centre Airport (YTZ)
Sat, 13 feb
1h 55min
Direct
23:30
Chicago, O'Hare International Airport (ORD)
Sat, 13 feb
236 S$
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Toronto City Centre Airport (YTZ)
Thu, 18 feb
1h 55min
Direct
23:30
Chicago, O'Hare International Airport (ORD)
Thu, 18 feb
258 S$
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Toronto City Centre Airport (YTZ)
Sat, 20 feb
1h 55min
Direct
23:30
Chicago, O'Hare International Airport (ORD)
Sat, 20 feb
236 S$
Passaredo Linhas Aereas
P3 2705
21:35
Toronto, Toronto City Centre Airport (YTZ)
Mon, 22 feb
1h 55min
Direct
23:30
Chicago, O'Hare International Airport (ORD)
Mon, 22 feb
258 S$
Passaredo Linhas Aereas
P3 2703
15:10
Toronto, Toronto City Centre Airport (YTZ)
Sat, 27 feb
1h 55min
Direct
17:05
Chicago, O'Hare International Airport (ORD)
Sat, 27 feb
236 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 144 S$ · max: 299 S$
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Sat
Sun
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299 S$
16
Good deal
144 S$
17
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no data
18
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231 S$
19
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214 S$
20
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no data
21
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237 S$
22
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251 S$
23
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156 S$
24
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243 S$
25
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242 S$
26
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152 S$
28
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29
Good deal
149 S$
30
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Cheap flights Toronto to Chicago

Passaredo Linhas Aereas
Passaredo Linhas Aereas
Mon, Tue, Wed, Thu, Sat, Sun
Price from
S$141
Air Canada
Air Canada
Mon, Tue, Wed, Thu, Fri, Sat
Price from
S$149
Porter Airlines
Porter Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$152
United Airlines
United Airlines
Wed, Fri, Sun
Price from
S$154
American Airlines
American Airlines
Sun
Price from
S$182

Popular destinations from Toronto

All →
YTO
Toronto — Montreal
Canada → Canada
YHU
from
S$53
YTO
Toronto — Montreal
Canada → Canada
YMQ
from
S$53
YTO
Toronto — Winnipeg
Canada → Canada
YWG
from
S$55
YTO
Toronto — Ottawa
Canada → Canada
YOW
from
S$59
YTO
Toronto — Halifax
Canada → Canada
YHZ
from
S$64
YTO
Toronto — Regina
Canada → Canada
YQR
from
S$76
YTO
Toronto — Montreal
Canada → Canada
YUL
from
S$76
YTO
Toronto — Calgary
Canada → Canada
YYC
from
S$89
YTO
Toronto — Thunder Bay
Canada → Canada
YQT
from
S$89

Popular destinations to Chicago

All →
HOU
Houston — Chicago
United States → United States
CHI
from
S$27
NYC
New York — Chicago
United States → United States
CHI
from
S$28
PHX
Phoenix — Chicago
United States → United States
CHI
from
S$30
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
S$32
ATL
Atlanta — Chicago
United States → United States
CHI
from
S$34
BNA
Nashville — Chicago
United States → United States
CHI
from
S$35
LAX
Los Angeles — Chicago
United States → United States
CHI
from
S$39
ORL
Orlando — Chicago
United States → United States
CHI
from
S$40
MIA
Miami — Chicago
United States → United States
CHI
from
S$41

Cheap flights Toronto to Chicago

Interesting facts about the route

Flight time

1h 55min

Distance

711 km

Average price

S$172

Most frequent flight

PD 2393

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

S$11

Buy

change

2 GB

data

15

days

S$16

Buy

change

5 GB

data

30

days

S$18

Buy

change

3 GB

data

30

days

S$20

Buy

change

5 GB

data

30

days

S$29

Buy

Frequently Asked Questions

The average ticket price Toronto Chicago is S$172. The cheapest ticket costs S$144, operated by Passaredo Linhas Aereas, flight 2393, departing Toronto on 16 September at 17:45, arriving Chicago on 16 September at 19:35.
The average flight time is 1 hour 50 minutes. The fastest flight takes 1 hour 50 minutes, flight 2387 operated by Passaredo Linhas Aereas, departing Toronto on 15 September at 14:10, arriving Chicago on 15 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.