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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 3507
16:50
Orlando, Orlando International Airport (MCO)
Wed, 16 sep
6h 1min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
19 385 ₹
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
19 385 ₹
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
16 954 ₹
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
20 179 ₹
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
19 725 ₹
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
19 385 ₹
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
16 100 ₹
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
11 122 ₹
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
10 456 ₹
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
16 360 ₹
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
12 288 ₹
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
15 340 ₹
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
11 729 ₹
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
16 196 ₹
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
11 435 ₹
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
12 137 ₹
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
9 779 ₹
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
10 160 ₹
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
6 904 ₹
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
13 992 ₹
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
14 630 ₹
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
8 726 ₹
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
15 239 ₹
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
11 415 ₹
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
15 459 ₹
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
11 804 ₹
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
10 277 ₹
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
11 880 ₹
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
11 804 ₹
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
10 571 ₹
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
11 773 ₹
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
12 544 ₹
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
12 852 ₹
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
12 700 ₹
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
18 052 ₹
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
29 953 ₹
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
9 300 ₹
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
15 232 ₹
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
10 124 ₹
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
11 571 ₹
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
14 477 ₹
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
7 479 ₹
Southwest Airlines
WN 2310
12:40
Orlando, Orlando International Airport (MCO)
Thu, 31 dec
5h 35min
1 stop
18:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 31 dec
14 676 ₹
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
14 024 ₹
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
16 644 ₹
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
15 091 ₹
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
19 064 ₹

Low price calendar

September 2026
Price chart (September 2026)
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19385 ₹
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16954 ₹
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20179 ₹
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19725 ₹
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11122 ₹
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10456 ₹
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11435 ₹

Cheap flights Orlando to Chicago Midway International Airport

Frontier Airlines
Frontier Airlines
Tue, Wed, Thu, Fri, Sat, Sun
Price from
₹6 904
Southwest Airlines
Southwest Airlines
Wed, Thu, Fri, Sat, Sun
Price from
₹10 456

Popular destinations from Orlando

All →
ORL
Orlando — New York
United States → United States
NYC
from
₹1 743
ORL
Orlando — New York
United States → United States
LGA
from
₹1 743
ORL
Orlando — Atlanta
United States → United States
ATL
from
₹1 884
ORL
Orlando — Houston
United States → United States
HOU
from
₹2 054
ORL
Orlando — Nashville
United States → United States
BNA
from
₹2 168
ORL
Orlando — Austin
United States → United States
AUS
from
₹2 455
ORL
Orlando — Las Vegas
United States → United States
LAS
from
₹2 495
ORL
Orlando — Houston
United States → United States
IAH
from
₹2 582
ORL
Orlando — Boston
United States → United States
BOS
from
₹2 610

Popular destinations to Chicago Midway International Airport

All →
NYC
New York — Chicago
United States → United States
MDW
from
₹2 148
ATL
Atlanta — Chicago
United States → United States
MDW
from
₹3 531
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
₹5 233
HOU
Houston — Chicago
United States → United States
MDW
from
₹5 746
DFW
Dallas — Chicago
United States → United States
MDW
from
₹6 747
PHL
Philadelphia — Chicago
United States → United States
MDW
from
₹6 790
TPA
Tampa — Chicago
United States → United States
MDW
from
₹7 079
MIA
Miami — Chicago
United States → United States
MDW
from
₹7 229

Cheap flights Orlando to Chicago Midway International Airport

Interesting facts about the route

Flight time

6h 1min

Distance

1 594 km

Average price

₹12 852

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

₹863

Buy

change

2 GB

data

15

days

₹1199

Buy

change

5 GB

data

30

days

₹1343

Buy

change

3 GB

data

30

days

₹1535

Buy

change

5 GB

data

30

days

₹2158

Buy

Frequently Asked Questions

The average ticket price Orlando Chicago Midway International Airport is ₹12 852. The cheapest ticket costs ₹16 954, 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.