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: Sat May 7 2016 Return: Sat May 14 2016 Trip spans 8 days
Southwest
Southwest
MCO
12:20p
MDW
3:05p
2h 45m
nonstop
MDW
1:50p
MCO
4:25p
2h 35m
nonstop
Depart: Mon Feb 29 2016 Return: Mon Mar 7 2016 Trip spans 8 days
Delta
Delta
MCO
2:35a
MDW
10:42a
8h 07m
1 stop
MDW
7:15a
MCO
1:29p
6h 14m
1 stop
Depart: Tue Mar 1 2016 Return: Wed Mar 2 2016 Trip spans 2 days
Delta
Delta
MCO
1:15a
MDW
5:35a
4h 20m
1 stop
MDW
4:23a
MCO
8:54a
4h 31m
1 stop
Depart: Wed Mar 2 2016 Return: Sun Mar 6 2016 Trip spans 5 days
Delta
Delta
MCO
3:20a
MDW
7:39a
4h 19m
1 stop
MDW
2:05a
MCO
6:24a
4h 19m
1 stop
Depart: Thu Mar 3 2016 Return: Sun Mar 6 2016 Trip spans 4 days
Delta
Delta
MCO
12:20a
MDW
5:34a
5h 14m
1 stop
MDW
7:15a
MCO
11:23a
4h 08m
1 stop
Depart: Fri Mar 4 2016 Return: Sun Mar 6 2016 Trip spans 3 days
Delta
Delta
MCO
5:25a
MDW
10:54a
5h 29m
1 stop
MDW
7:15a
MCO
11:23a
4h 08m
1 stop
Depart: Sat Mar 5 2016 Return: Sun Mar 6 2016 Trip spans 2 days
Delta
Delta
MCO
6:20a
MDW
10:53a
4h 33m
1 stop
MDW
1:00a
MCO
5:29a
4h 29m
1 stop
Depart: Sun Mar 6 2016 Return: Mon Mar 14 2016 Trip spans 8 days
Delta
Delta
MCO
12:20a
MDW
5:35a
5h 15m
1 stop
MDW
10:00a
MCO
5:27p
7h 27m
1 stop
Depart: Mon Mar 7 2016 Return: Mon Mar 14 2016 Trip spans 7 days
Delta
Delta
MCO
2:20a
MDW
9:07a
6h 47m
1 stop
MDW
11:31a
MCO
4:02p
4h 31m
1 stop
Depart: Tue Mar 8 2016 Return: Wed Mar 9 2016 Trip spans 2 days
Delta
Delta
MCO
6:20a
MDW
10:54a
4h 34m
1 stop
MDW
10:31a
MCO
3:02p
4h 31m
1 stop
Depart: Wed Mar 9 2016 Return: Mon Mar 14 2016 Trip spans 5 days
Delta
Delta
MCO
2:20a
MDW
7:39a
5h 19m
1 stop
MDW
2:20p
MCO
6:40p
4h 20m
1 stop
Depart: Thu Mar 10 2016 Return: Mon Mar 14 2016 Trip spans 4 days
Delta
Delta
MCO
12:20a
MDW
5:34a
5h 14m
1 stop
MDW
2:30p
MCO
7:39p
5h 09m
1 stop
Depart: Fri Mar 11 2016 Return: Mon Mar 14 2016 Trip spans 3 days
Delta
Delta
MCO
2:20a
MDW
7:39a
5h 19m
1 stop
MDW
2:20p
MCO
6:40p
4h 20m
1 stop
Depart: Sat Mar 12 2016 Return: Wed Mar 16 2016 Trip spans 4 days
Delta
Delta
MCO
5:50a
MDW
10:53a
5h 03m
1 stop
MDW
8:15a
MCO
1:26p
5h 11m
1 stop
Depart: Sun Feb 14 2016 Return: Tue Mar 1 2016 Trip spans 17 days
Delta
Delta
MCO
1:00a
MDW
7:50a
6h 50m
1 stop
MDW
11:40a
MCO
5:16p
5h 36m
1 stop
Depart: Tue Feb 16 2016 Return: Sun Feb 28 2016 Trip spans 13 days
Delta
Delta
MCO
11:10a
MDW
4:50p
5h 40m
1 stop
MDW
1:21p
MCO
6:46p
5h 25m
1 stop
Depart: Wed Feb 17 2016 Return: Mon Feb 29 2016 Trip spans 13 days
Delta
Delta
MCO
12:30p
MDW
6:48p
6h 18m
1 stop
MDW
9:26a
MCO
2:04p
4h 38m
1 stop
Depart: Thu Feb 18 2016 Return: Mon Feb 29 2016 Trip spans 12 days
Delta
Delta
MCO
6:32a
MDW
12:46p
6h 14m
1 stop
MDW
7:25a
MCO
12:31p
5h 06m
1 stop
Depart: Fri Feb 19 2016 Return: Mon Feb 29 2016 Trip spans 11 days
Delta
Delta
MCO
4:28a
MDW
12:46p
8h 18m
1 stop
MDW
2:05a
MCO
6:29a
4h 24m
1 stop
Depart: Sat Feb 20 2016 Return: Mon Feb 29 2016 Trip spans 10 days
Delta
Delta
MCO
4:28a
MDW
10:40a
6h 12m
1 stop
MDW
5:10a
MCO
9:31a
4h 21m
1 stop
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
2177 6:55 am 8:45 am Mar 13 - Apr 10
2177 6:55 am 8:45 am Mar 10 - Mar 11
2177 6:55 am 8:45 am Mar 14 - Apr 11
4499 7:25 am 9:15 am Mar 12 - Mar 12
3067 7:35 am 9:30 am Jan 30 - Mar 5
4179 8:05 am 9:55 am Mar 12 - Mar 12
2094 8:30 am 10:25 am Mar 9 - Mar 9
566 8:30 am 10:25 am Feb 1 - Mar 8
4124 8:45 am 10:35 am Mar 12 - Mar 12
2849 9:50 am 11:45 am Feb 14 - Mar 6
1675 9:55 am 11:50 am Feb 1 - Mar 8
596 9:55 am 11:50 am Mar 9 - Mar 9
1117 10:05 am 11:55 am Mar 10 - Mar 11
1117 10:05 am 11:55 am Mar 13 - Apr 11
3702 10:20 am 12:15 pm Jan 30 - Mar 5
952 10:30 am 12:25 pm Feb 14 - Mar 6
4463 11:05 am 12:55 pm Mar 12 - Mar 12
941 11:15 am 1:05 pm Mar 13 - Apr 11
941 11:15 am 1:05 pm Mar 10 - Mar 11
1914 11:45 am 1:40 pm Mar 9 - Mar 9
520 11:45 am 1:40 pm Feb 8 - Mar 8
424 11:50 am 1:40 pm Mar 12 - Mar 12
1594 12:20 pm 2:10 pm Mar 12 - Mar 12
1075 12:30 pm 2:20 pm Feb 20 - Feb 20
1075 12:30 pm 2:20 pm Feb 27 - Mar 5
699 1:05 pm 2:55 pm Mar 10 - Mar 11
699 1:05 pm 2:55 pm Mar 13 - Apr 11
1959 2:20 pm 4:10 pm Jan 30 - Mar 5
2253 2:35 pm 4:25 pm Mar 12 - Mar 12
884 2:55 pm 4:45 pm Mar 14 - Mar 25
884 2:55 pm 4:45 pm Mar 13 - Apr 10
884 2:55 pm 4:45 pm Mar 10 - Mar 11
2590 3:10 pm 5:00 pm Mar 12 - Mar 12
1723 3:15 pm 5:10 pm Mar 6 - Mar 8
1723 3:15 pm 5:10 pm Feb 28 - Mar 4
1723 3:15 pm 5:10 pm Feb 8 - Feb 26
5118 3:15 pm 5:10 pm Mar 9 - Mar 9
4440 4:15 pm 6:05 pm Mar 13 - Apr 10
4440 4:15 pm 6:05 pm Mar 10 - Mar 11
4440 4:15 pm 6:05 pm Mar 14 - Apr 11
536 4:20 pm 6:15 pm Jan 31 - Mar 8
5252 4:35 pm 6:30 pm Jan 30 - Mar 5
2935 4:40 pm 6:30 pm Mar 12 - Mar 12
4574 5:10 pm 7:00 pm Mar 12 - Mar 12
1960 5:25 pm 7:20 pm Mar 9 - Mar 9
4258 5:50 pm 7:40 pm Mar 13 - Apr 11
4258 5:50 pm 7:40 pm Mar 10 - Mar 11
806 6:20 pm 8:10 pm Mar 12 - Mar 12
1331 6:25 pm 8:20 pm Jan 30 - Mar 5
536 7:05 pm 8:55 pm Mar 12 - Mar 12
1486 8:15 pm 10:05 pm Mar 9 - Mar 9
423 8:15 pm 10:10 pm Feb 8 - Mar 8
1590 8:20 pm 10:15 pm Jan 30 - Mar 5
2113 9:05 pm 10:55 pm Mar 13 - Apr 10
2113 9:05 pm 10:55 pm Mar 14 - Apr 11
2113 9:05 pm 10:55 pm Mar 10 - Mar 11
724 9:25 pm 11:20 pm Feb 9 - Mar 8
18 10:05 pm 11:50 pm Mar 12 - Mar 12
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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

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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
$207
Destination

Chicago
$207