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Cheap flights Orlando (Executive) to Chicago Midway International Airport

1 passenger, economy

Cheap flights Orlando to Chicago Midway International Airport

Compare prices, duration and stops

Frontier Airlines
F9 4017
10:00
Orlando, Orlando International Airport (MCO)
Thu, 17 sep
6h 59min
1 stop
16:59
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
150 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Thu, 17 sep
5h 56min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
131 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Fri, 18 sep
6h 1min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep
156 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Sat, 19 sep
6h 1min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
153 £
Frontier Airlines
F9 4017
10:00
Orlando, Orlando International Airport (MCO)
Sun, 20 sep
6h 59min
1 stop
16:59
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
150 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Tue, 22 sep
5h 56min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
125 £
Frontier Airlines
F9 4025
21:19
Orlando, Orlando International Airport (MCO)
Tue, 22 sep
25h 32min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep +1
86 £
Southwest Airlines
WN 359
11:40
Orlando, Orlando International Airport (MCO)
Wed, 23 sep
2h 45min
Direct
14:25
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
81 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Thu, 24 sep
5h 56min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
127 £
Frontier Airlines
F9 4025
21:19
Orlando, Orlando International Airport (MCO)
Fri, 25 sep
7h 25min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep +1
95 £
Frontier Airlines
F9 4017
10:00
Orlando, Orlando International Airport (MCO)
Sat, 26 sep
6h 59min
1 stop
16:59
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
119 £
Frontier Airlines
F9 1241
13:30
Orlando, Orlando International Airport (MCO)
Tue, 29 sep
9h 16min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
91 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Tue, 29 sep
5h 56min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
125 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Wed, 30 sep
6h 1min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
88 £
Frontier Airlines
F9 4025
21:19
Orlando, Orlando International Airport (MCO)
Fri, 2 oct
7h 25min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct +1
94 £
Frontier Airlines
F9 3507
16:50
Orlando, Orlando International Airport (MCO)
Sat, 3 oct
6h 1min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
76 £
Frontier Airlines
F9 1241
13:30
Orlando, Orlando International Airport (MCO)
Wed, 7 oct
9h 21min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
79 £
Frontier Airlines
F9 3507 Best price
16:50
Orlando, Orlando International Airport (MCO)
Wed, 7 oct
6h 1min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
53 £
Frontier Airlines
F9 1563
09:25
Orlando, Orlando International Airport (MCO)
Fri, 9 oct
17h 57min
1 stop
03:22
Chicago, Chicago Midway International Airport (MDW)
Sat, 10 oct +1
108 £
Frontier Airlines
F9 3975
18:52
Orlando, Orlando International Airport (MCO)
Fri, 9 oct
8h 30min
1 stop
03:22
Chicago, Chicago Midway International Airport (MDW)
Sat, 10 oct +1
113 £
Frontier Airlines
F9 1241
11:10
Orlando, Orlando International Airport (MCO)
Sat, 10 oct
17h 33min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Sun, 11 oct +1
68 £
Frontier Airlines
F9 1563
10:07
Orlando, Orlando International Airport (MCO)
Sun, 11 oct
18h 36min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Mon, 12 oct +1
118 £
Southwest Airlines
WN 2825
11:30
Orlando, Orlando International Airport (MCO)
Sat, 31 oct
2h 50min
Direct
14:20
Chicago, Chicago Midway International Airport (MDW)
Sat, 31 oct
88 £
Frontier Airlines
F9 1563
13:07
Orlando, Orlando International Airport (MCO)
Sun, 1 nov
10h 40min
1 stop
23:47
Chicago, Chicago Midway International Airport (MDW)
Sun, 1 nov
120 £
Southwest Airlines
WN 2595
00:20
Orlando, Orlando International Airport (MCO)
Thu, 5 nov
2h 55min
Direct
03:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 5 nov
91 £
Frontier Airlines
F9 1915
11:25
Orlando, Orlando International Airport (MCO)
Thu, 5 nov
15h 5min
1 stop
02:30
Chicago, Chicago Midway International Airport (MDW)
Fri, 6 nov +1
79 £
Southwest Airlines
WN 246
14:05
Orlando, Orlando International Airport (MCO)
Thu, 5 nov
4h 15min
Direct
18:20
Chicago, Chicago Midway International Airport (MDW)
Thu, 5 nov
92 £
Southwest Airlines
WN 2806
23:40
Orlando, Orlando International Airport (MCO)
Thu, 5 nov
2h 55min
Direct
02:35
Chicago, Chicago Midway International Airport (MDW)
Fri, 6 nov +1
91 £
Frontier Airlines
F9 1915
11:25
Orlando, Orlando International Airport (MCO)
Fri, 6 nov
27h 35min
1 stop
15:00
Chicago, Chicago Midway International Airport (MDW)
Sat, 7 nov +1
82 £
Southwest Airlines
WN 1376
18:00
Orlando, Orlando International Airport (MCO)
Sat, 14 nov
8h
1 stop
02:00
Chicago, Chicago Midway International Airport (MDW)
Sun, 15 nov +1
91 £
Frontier Airlines
F9 4025
22:03
Orlando, Orlando International Airport (MCO)
Sat, 14 nov
7h 44min
1 stop
05:47
Chicago, Chicago Midway International Airport (MDW)
Sun, 15 nov +1
97 £
Frontier Airlines
F9 3507
17:54
Orlando, Orlando International Airport (MCO)
Thu, 19 nov
5h 53min
1 stop
23:47
Chicago, Chicago Midway International Airport (MDW)
Thu, 19 nov
82 £
Frontier Airlines
F9 1457
15:23
Orlando, Orlando International Airport (MCO)
Tue, 24 nov
3h 1min
Direct
18:24
Chicago, Chicago Midway International Airport (MDW)
Tue, 24 nov
99 £
Frontier Airlines
F9 1457
22:46
Orlando, Orlando International Airport (MCO)
Tue, 24 nov
3h 1min
Direct
01:47
Chicago, Chicago Midway International Airport (MDW)
Wed, 25 nov +1
98 £
Frontier Airlines
F9 1457
15:23
Orlando, Orlando International Airport (MCO)
Fri, 27 nov
3h 1min
Direct
18:24
Chicago, Chicago Midway International Airport (MDW)
Fri, 27 nov
140 £
Southwest Airlines
WN 2814
03:15
Orlando, Orlando International Airport (MCO)
Sun, 29 nov
9h 30min
1 stop
12:45
Chicago, Chicago Midway International Airport (MDW)
Sun, 29 nov
232 £
Frontier Airlines
F9 1457
22:01
Orlando, Orlando International Airport (MCO)
Thu, 3 dec
3h 1min
Direct
01:02
Chicago, Chicago Midway International Airport (MDW)
Fri, 4 dec +1
72 £
Frontier Airlines
F9 1457
22:01
Orlando, Orlando International Airport (MCO)
Wed, 23 dec
3h 1min
Direct
01:02
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 dec +1
118 £
Southwest Airlines
WN 1731
21:10
Orlando, Orlando International Airport (MCO)
Thu, 24 dec
2h 55min
Direct
00:05
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 dec +1
78 £
Southwest Airlines
WN 2595
00:20
Orlando, Orlando International Airport (MCO)
Fri, 25 dec
2h 55min
Direct
03:15
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 dec
89 £
Southwest Airlines
WN 1211
13:10
Orlando, Orlando International Airport (MCO)
Wed, 30 dec
4h 50min
Direct
18:00
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 dec
112 £
Frontier Airlines
F9 1457
22:01
Orlando, Orlando International Airport (MCO)
Wed, 30 dec
3h 1min
Direct
01:02
Chicago, Chicago Midway International Airport (MDW)
Thu, 31 dec +1
58 £
Southwest Airlines
WN 2310
12:40
Orlando, Orlando International Airport (MCO)
Thu, 31 dec
9h 25min
1 stop
22:05
Chicago, Chicago Midway International Airport (MDW)
Thu, 31 dec
103 £
Frontier Airlines
F9 1241
14:27
Orlando, Orlando International Airport (MCO)
Thu, 31 dec
7h 48min
1 stop
22:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 31 dec
108 £
Frontier Airlines
F9 1457
22:01
Orlando, Orlando International Airport (MCO)
Thu, 31 dec
3h 1min
Direct
01:02
Chicago, Chicago Midway International Airport (MDW)
Fri, 1 jan +1
129 £
Southwest Airlines
WN 1346
22:15
Orlando, Orlando International Airport (MCO)
Thu, 31 dec
6h 25min
1 stop
04:40
Chicago, Chicago Midway International Airport (MDW)
Fri, 1 jan +1
117 £
Frontier Airlines
F9 1241
14:27
Orlando, Orlando International Airport (MCO)
Sun, 3 jan
7h 48min
1 stop
22:15
Chicago, Chicago Midway International Airport (MDW)
Sun, 3 jan
147 £

Low price calendar

September 2026
Price chart (September 2026)
min: 81 £ · max: 156 £
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131 £
18
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156 £
19
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153 £
20
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150 £
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22
Good deal
86 £
23
Good deal
81 £
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127 £
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95 £
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119 £
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91 £
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88 £

Cheap flights Orlando to Chicago Midway International Airport

Frontier Airlines
Frontier Airlines
Tue, Wed, Thu, Fri, Sat, Sun
Price from
£53
Southwest Airlines
Southwest Airlines
Wed, Thu, Fri, Sat, Sun
Price from
£81

Popular destinations from Orlando

All →
ORL
Orlando — New York
United States → United States
NYC
from
£13
ORL
Orlando — New York
United States → United States
LGA
from
£13
ORL
Orlando — Atlanta
United States → United States
ATL
from
£15
ORL
Orlando — Houston
United States → United States
HOU
from
£16
ORL
Orlando — Nashville
United States → United States
BNA
from
£17
ORL
Orlando — Austin
United States → United States
AUS
from
£19
ORL
Orlando — Las Vegas
United States → United States
LAS
from
£19
ORL
Orlando — Houston
United States → United States
IAH
from
£20
ORL
Orlando — Boston
United States → United States
BOS
from
£20

Popular destinations to Chicago Midway International Airport

All →
NYC
New York — Chicago
United States → United States
MDW
from
£17
ATL
Atlanta — Chicago
United States → United States
MDW
from
£27
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
£40
HOU
Houston — Chicago
United States → United States
MDW
from
£44
DFW
Dallas — Chicago
United States → United States
MDW
from
£52
PHL
Philadelphia — Chicago
United States → United States
MDW
from
£53
TPA
Tampa — Chicago
United States → United States
MDW
from
£55
MIA
Miami — Chicago
United States → United States
MDW
from
£56

Cheap flights Orlando to Chicago Midway International Airport

Interesting facts about the route

Flight time

6h 1min

Distance

1 594 km

Average price

£98

Most frequent flight

F9 3507

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

£7

Buy

change

2 GB

data

15

days

£9

Buy

change

5 GB

data

30

days

£10

Buy

change

3 GB

data

30

days

£12

Buy

change

5 GB

data

30

days

£17

Buy

Frequently Asked Questions

The average ticket price Orlando Chicago Midway International Airport is £98. The cheapest ticket costs £131, operated by Frontier Airlines, flight 3507, departing Orlando on 17 September at 16:50, arriving Chicago Midway International Airport on 17 September at 22:46.
The average flight time is 6 hours 1 minute. The fastest flight takes 5 hours 56 minutes, flight 3507 operated by Frontier Airlines, departing Orlando on 17 September at 16:50, arriving Chicago Midway International Airport on 17 September at 22:46.
Flights on the Orlando - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.
The distance from Orlando to Chicago Midway International Airport is 1594 km.