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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 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
84 £
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
135 £
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
83 £
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
125 £
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
140 £
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
146 £
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
91 £
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
83 £
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
142 £
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
141 £
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
82 £
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
81 £
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
90 £
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
90 £
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
89 £
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
91 £
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
82 £
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
87 £
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
89 £
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
89 £
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
90 £
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
82 £
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
87 £
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
156 £
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
90 £
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
91 £
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
90 £
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
167 £
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
125 £
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
95 £
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
90 £
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
124 £
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
87 £
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
106 £
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
94 £
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
118 £
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
129 £
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
152 £
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
138 £
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
151 £
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
138 £
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
151 £
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
138 £
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
151 £
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
138 £

Low price calendar

September 2026
Price chart (September 2026)
min: 84 £ · max: 158 £
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Sun
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158 £
14
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16
Good deal
84 £
17
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135 £
19
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125 £
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140 £
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146 £
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91 £
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141 £
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90 £
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Good deal
87 £
30
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Cheap flights Toronto to Chicago

Passaredo Linhas Aereas
Passaredo Linhas Aereas
Mon, Wed, Thu, Sat, Sun
Price from
£82
Air Canada
Air Canada
Mon, Tue, Wed, Thu, Fri, Sat
Price from
£87
Porter Airlines
Porter Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
£90
United Airlines
United Airlines
Wed, Fri, Sun
Price from
£90
American Airlines
American Airlines
Sun
Price from
£106

Popular destinations from Toronto

All →
YTO
Toronto — Montreal
Canada → Canada
YMQ
from
£31
YTO
Toronto — Montreal
Canada → Canada
YHU
from
£31
YTO
Toronto — Winnipeg
Canada → Canada
YWG
from
£32
YTO
Toronto — Ottawa
Canada → Canada
YOW
from
£34
YTO
Toronto — Halifax
Canada → Canada
YHZ
from
£37
YTO
Toronto — Regina
Canada → Canada
YQR
from
£44
YTO
Toronto — Montreal
Canada → Canada
YUL
from
£44
YTO
Toronto — Calgary
Canada → Canada
YYC
from
£52
YTO
Toronto — Thunder Bay
Canada → Canada
YQT
from
£52

Popular destinations to Chicago

All →
HOU
Houston — Chicago
United States → United States
CHI
from
£16
NYC
New York — Chicago
United States → United States
CHI
from
£17
PHX
Phoenix — Chicago
United States → United States
CHI
from
£18
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
£19
ATL
Atlanta — Chicago
United States → United States
CHI
from
£20
BNA
Nashville — Chicago
United States → United States
CHI
from
£20
LAX
Los Angeles — Chicago
United States → United States
CHI
from
£23
ORL
Orlando — Chicago
United States → United States
CHI
from
£23
MIA
Miami — Chicago
United States → United States
CHI
from
£24

Cheap flights Toronto to Chicago

Interesting facts about the route

Flight time

1h 55min

Distance

714 km

Average price

£95

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

£7

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2 GB

data

15

days

£9

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change

5 GB

data

30

days

£10

Buy

change

3 GB

data

30

days

£12

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change

5 GB

data

30

days

£17

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Frequently Asked Questions

The average ticket price Toronto Chicago is £95. The cheapest ticket costs £84, 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 2393 operated by Passaredo Linhas Aereas, departing Toronto on 16 September at 17:45, arriving Chicago on 16 September at 19:35.
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 714 km.