Find Deals on Flights from Chicago Midway to Orlando (MDW - ORL)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago Midway to Orlando

(Round-trip)
Depart: Tue Nov 15 2016 Return: Wed Nov 16 2016 Trip spans 2 days
Major Airline
Major Airline
MDW
2:10p
MCO
4:45p
2h 35m
nonstop
MCO
4:55p
MDW
7:40p
2h 45m
nonstop
Depart: Tue Oct 11 2016 Return: Wed Oct 12 2016 Trip spans 2 days
Delta
Delta
MDW
1:55p
MCO
6:50p
4h 55m
1 stop
MCO
8:15a
MDW
12:58p
4h 43m
1 stop
Depart: Tue Jan 10 2017 Return: Tue Jan 17 2017 Trip spans 8 days
Southwest
Southwest
MDW
2:20a
MCO
4:55a
2h 35m
nonstop
MCO
3:35p
MDW
6:25p
2h 50m
nonstop
Depart: Mon Nov 14 2016 Return: Wed Nov 16 2016 Trip spans 3 days
Major Airline
Major Airline
MDW
11:30a
MCO
2:05p
2h 35m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Thu Dec 8 2016 Return: Mon Dec 12 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
11:30a
MCO
2:05p
2h 35m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Sun Dec 4 2016 Return: Thu Dec 8 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
3:25p
MCO
6:05p
2h 40m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Wed Oct 12 2016 Return: Tue Oct 18 2016 Trip spans 7 days
Delta
Delta
MDW
6:23a
MCO
10:40a
4h 17m
1 stop
MCO
10:10a
MDW
2:57p
4h 47m
1 stop
Depart: Sat Jan 14 2017 Return: Sat Jan 21 2017 Trip spans 8 days
Southwest
Southwest
MDW
11:30a
MCO
2:00p
2h 30m
nonstop
MCO
2:10p
MDW
5:00p
2h 50m
nonstop
Depart: Tue Nov 29 2016 Return: Tue Dec 6 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
3:15p
MCO
5:55p
2h 40m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Mon Oct 17 2016 Return: Tue Oct 18 2016 Trip spans 2 days
Delta
Delta
MDW
3:38p
MCO
7:58p
4h 20m
1 stop
MCO
2:20a
MDW
6:48a
4h 28m
1 stop
Depart: Fri Dec 9 2016 Return: Tue Dec 13 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
11:30a
MCO
2:05p
2h 35m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Tue Oct 18 2016 Return: Wed Oct 19 2016 Trip spans 2 days
Delta
Delta
MDW
1:55p
MCO
7:58p
6h 03m
1 stop
MCO
9:21a
MDW
3:58p
6h 37m
1 stop
Depart: Sun Nov 6 2016 Return: Wed Nov 9 2016 Trip spans 4 days
Major Airline
Major Airline
MDW
3:15p
MCO
5:55p
2h 40m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Sat Oct 22 2016 Return: Wed Oct 26 2016 Trip spans 5 days
Delta
Delta
MDW
1:03p
MCO
6:50p
5h 47m
1 stop
MCO
2:20a
MDW
6:48a
4h 28m
1 stop
Depart: Sun Nov 13 2016 Return: Wed Nov 16 2016 Trip spans 4 days
Major Airline
Major Airline
MDW
12:50a
MCO
3:30a
2h 40m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Mon Oct 24 2016 Return: Tue Oct 25 2016 Trip spans 2 days
Delta
Delta
MDW
1:55p
MCO
7:58p
6h 03m
1 stop
MCO
4:15a
MDW
9:26a
5h 11m
1 stop
Depart: Wed Nov 30 2016 Return: Wed Dec 7 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
4:20a
MCO
7:00a
2h 40m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Depart: Sun Jan 1 2017 Return: Thu Jan 5 2017 Trip spans 5 days
Southwest
Southwest
MDW
3:15p
MCO
5:55p
2h 40m
nonstop
MCO
11:25a
MDW
4:00p
4h 35m
1 stop
Depart: Tue Oct 25 2016 Return: Wed Oct 26 2016 Trip spans 2 days
Delta
Delta
MDW
2:00a
MCO
6:21a
4h 21m
1 stop
MCO
3:25p
MDW
7:55p
4h 30m
1 stop
Depart: Sat Dec 3 2016 Return: Tue Dec 6 2016 Trip spans 4 days
Major Airline
Major Airline
MDW
10:40a
MCO
1:15p
2h 35m
nonstop
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
Select an airline:  Southwest
Direct flights MDW to ORL on Southwest
Flight # Depart MDW Arrive MCO Sun Mon Tue Wed Thu Fri Sat Valid Between
342 6:30 am 10:00 am Oct 2 - Nov 4
2532 6:55 am 10:25 am Sep 24 - Nov 5
4477 7:35 am 11:05 am Oct 2 - Oct 30
4477 7:35 am 11:05 am Nov 1 - Nov 4
497 7:40 am 11:10 am Oct 31 - Oct 31
3574 7:45 am 11:15 am Oct 8 - Nov 5
3417 9:15 am 12:50 pm Oct 8 - Nov 5
1054 10:05 am 1:35 pm Oct 8 - Nov 5
575 10:20 am 1:45 pm Oct 2 - Nov 4
3091 11:30 am 3:00 pm Oct 2 - Nov 4
1253 12:25 pm 3:55 pm Oct 8 - Nov 5
772 1:10 pm 4:40 pm Oct 8 - Nov 5
3730 3:20 pm 6:50 pm Oct 8 - Oct 29
2234 3:35 pm 7:05 pm Oct 30 - Oct 30
2421 3:35 pm 7:05 pm Oct 31 - Oct 31
3230 3:35 pm 7:05 pm Oct 2 - Oct 28
3230 3:35 pm 7:05 pm Nov 1 - Nov 4
2128 4:10 pm 7:40 pm Oct 8 - Nov 5
829 6:05 pm 9:35 pm Oct 31 - Oct 31
2574 6:10 pm 9:40 pm Oct 8 - Oct 29
411 6:10 pm 9:40 pm Oct 2 - Oct 30
411 6:10 pm 9:40 pm Nov 1 - Nov 4
2986 7:30 pm 11:05 pm Oct 2 - Oct 30
2986 7:30 pm 11:05 pm Nov 1 - Nov 4
1442 7:35 pm 11:10 pm Oct 31 - Oct 31
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Why aren’t prices accurate 100% of the time?
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Airports
Origin

Chicago
$114
Destination

Orlando
$114
Airlines Airline reviews

5 travelers who booked a flight from Chicago to Orlando rated their chosen airlines with an average of 9.1.

Overall
9.6
Boarding
9.6
Crew
9.6
Comfort
9.6
Food
6.4
Entertainment
6.0