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

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 Orlando to Chicago Midway

(Round-trip)
Depart: Wed Nov 9 2016 Return: Mon Nov 14 2016 Trip spans 6 days
Major Airline
Major Airline
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
MDW
2:10p
MCO
4:45p
2h 35m
nonstop
Depart: Tue Nov 8 2016 Return: Fri Nov 11 2016 Trip spans 4 days
Delta
Delta
MCO
1:20a
MDW
8:28a
7h 08m
1 stop
MDW
2:45p
MCO
6:58p
4h 13m
1 stop
Depart: Tue Nov 15 2016 Return: Wed Nov 30 2016 Trip spans 16 days
Major Airline
Major Airline
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
MDW
11:30a
MCO
2:05p
2h 35m
nonstop
Depart: Tue Oct 4 2016 Return: Tue Oct 11 2016 Trip spans 8 days
Major Airline
Major Airline
MCO
3:25a
MDW
6:10a
2h 45m
nonstop
MDW
6:20a
MCO
11:40a
5h 20m
nonstop
Depart: Thu Nov 10 2016 Return: Tue Nov 15 2016 Trip spans 6 days
Delta
Delta
MCO
5:15a
MDW
9:24a
4h 09m
1 stop
MDW
5:20a
MCO
9:30a
4h 10m
1 stop
Depart: Wed Nov 30 2016 Return: Sat Dec 3 2016 Trip spans 4 days
Major Airline
Major Airline
MCO
1:05a
MDW
3:55a
2h 50m
nonstop
MDW
1:10p
MCO
3:50p
2h 40m
nonstop
Depart: Tue Oct 11 2016 Return: Fri Oct 14 2016 Trip spans 4 days
Delta
Delta
MCO
2:20a
MDW
8:44a
6h 24m
1 stop
MDW
8:16a
MCO
3:36p
7h 20m
1 stop
Depart: Thu Dec 8 2016 Return: Tue Dec 13 2016 Trip spans 6 days
Major Airline
Major Airline
MCO
6:05a
MDW
8:55a
2h 50m
nonstop
MDW
2:20a
MCO
5:00a
2h 40m
nonstop
Depart: Wed Oct 12 2016 Return: Mon Oct 17 2016 Trip spans 6 days
Delta
Delta
MCO
11:55a
MDW
5:19p
5h 24m
1 stop
MDW
3:38p
MCO
7:58p
4h 20m
1 stop
Depart: Thu Oct 13 2016 Return: Mon Oct 17 2016 Trip spans 5 days
Delta
Delta
MCO
2:20a
MDW
8:44a
6h 24m
1 stop
MDW
3:38p
MCO
7:58p
4h 20m
1 stop
Depart: Thu Dec 1 2016 Return: Mon Dec 5 2016 Trip spans 5 days
Major Airline
Major Airline
MCO
2:35a
MDW
5:25a
2h 50m
nonstop
MDW
2:20a
MCO
5:00a
2h 40m
nonstop
Depart: Tue Oct 18 2016 Return: Tue Oct 25 2016 Trip spans 8 days
Delta
Delta
MCO
3:25p
MDW
7:55p
4h 30m
1 stop
MDW
12:15p
MCO
5:30p
5h 15m
1 stop
Depart: Mon Oct 3 2016 Return: Wed Oct 5 2016 Trip spans 3 days
Major Airline
Major Airline
MCO
12:40p
MDW
3:30p
2h 50m
nonstop
MDW
6:20a
MCO
11:40a
5h 20m
nonstop
Depart: Thu Oct 20 2016 Return: Mon Oct 24 2016 Trip spans 5 days
Delta
Delta
MCO
3:50a
MDW
8:44a
4h 54m
1 stop
MDW
8:30a
MCO
2:34p
6h 04m
1 stop
Depart: Sat Oct 1 2016 Return: Mon Oct 3 2016 Trip spans 3 days
Major Airline
Major Airline
MCO
6:10a
MDW
8:55a
2h 45m
nonstop
MDW
3:30p
MCO
6:05p
2h 35m
nonstop
Depart: Thu Oct 27 2016 Return: Sat Oct 29 2016 Trip spans 3 days
Delta
Delta
MCO
4:21a
MDW
8:44a
4h 23m
1 stop
MDW
6:23a
MCO
11:25a
5h 02m
1 stop
Depart: Tue Nov 1 2016 Return: Sat Nov 5 2016 Trip spans 5 days
Major Airline
Major Airline
MCO
8:05a
MDW
10:50a
2h 45m
nonstop
MDW
4:55a
MCO
9:00a
4h 05m
nonstop
Depart: Wed Nov 2 2016 Return: Mon Nov 7 2016 Trip spans 6 days
Delta
Delta
MCO
6:20a
MDW
10:42a
4h 22m
1 stop
MDW
7:18a
MCO
1:38p
6h 20m
1 stop
Depart: Thu Nov 3 2016 Return: Sat Nov 5 2016 Trip spans 3 days
Delta
Delta
MCO
4:21a
MDW
8:44a
4h 23m
1 stop
MDW
1:03p
MCO
6:50p
5h 47m
1 stop
Depart: Fri Dec 2 2016 Return: Sun Dec 4 2016 Trip spans 3 days
Major Airline
Major Airline
MCO
10:55a
MDW
1:45p
2h 50m
nonstop
MDW
10:00a
MCO
12:35p
2h 35m
nonstop
Select an airline:  Southwest
Direct flights ORL to MDW on Southwest
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
2788 7:25 am 9:10 am Oct 3 - Nov 4
1014 8:25 am 10:10 am Oct 8 - Nov 5
771 8:35 am 10:20 am Oct 31 - Oct 31
820 8:35 am 10:20 am Nov 1 - Nov 4
820 8:35 am 10:20 am Oct 3 - Oct 28
2559 10:10 am 12:00 pm Oct 8 - Oct 29
3813 11:40 am 1:30 pm Oct 8 - Oct 29
541 11:55 am 1:40 pm Oct 2 - Oct 30
681 11:55 am 1:40 pm Oct 3 - Oct 28
720 11:55 am 1:40 pm Oct 31 - Oct 31
681 12:05 pm 1:50 pm Nov 1 - Nov 4
3251 12:45 pm 2:30 pm Oct 8 - Oct 22
6545 12:45 pm 2:30 pm Oct 29 - Oct 29
1210 1:20 pm 3:05 pm Sep 20 - Nov 4
2981 1:30 pm 3:15 pm Oct 8 - Nov 5
1580 3:25 pm 5:15 pm Oct 2 - Nov 4
1076 3:30 pm 5:20 pm Oct 8 - Nov 5
3645 4:00 pm 5:50 pm Oct 8 - Oct 29
417 4:40 pm 6:30 pm Nov 1 - Nov 4
417 4:40 pm 6:30 pm Oct 2 - Oct 30
417 4:40 pm 6:30 pm Oct 31 - Oct 31
856 6:05 pm 7:55 pm Oct 8 - Oct 29
204 7:05 pm 9:00 pm Nov 1 - Nov 4
204 7:05 pm 9:00 pm Oct 3 - Oct 28
173 7:10 pm 9:05 pm Oct 2 - Oct 30
828 7:25 pm 9:15 pm Oct 31 - Oct 31
861 7:55 pm 9:45 pm Oct 8 - Nov 5
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Orlando
$131
Destination

Chicago
$131
Airlines