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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Orlando to Chicago Midway

(Round-trip)
Depart: Mon Aug 3 2015 Return: Tue Aug 4 2015 Trip spans 2 days
Delta
Delta
MCO
2:30p
MDW
7:14p
4h 44m
1 stop
MDW
9:53a
MCO
2:40p
4h 47m
1 stop
Depart: Tue Aug 4 2015 Return: Tue Aug 11 2015 Trip spans 8 days
Delta
Delta
MCO
8:02a
MDW
12:59p
4h 57m
1 stop
MDW
9:53a
MCO
2:40p
4h 47m
1 stop
Depart: Wed Aug 5 2015 Return: Tue Aug 18 2015 Trip spans 14 days
Delta
Delta
MCO
8:05a
MDW
4:01p
7h 56m
1 stop
MDW
5:55a
MCO
10:36a
4h 41m
1 stop
Depart: Mon Aug 10 2015 Return: Sat Aug 15 2015 Trip spans 6 days
Delta
Delta
MCO
10:23a
MDW
6:35p
8h 12m
1 stop
MDW
2:14p
MCO
7:19p
5h 05m
1 stop
Depart: Tue Aug 11 2015 Return: Wed Aug 12 2015 Trip spans 2 days
Delta
Delta
MCO
3:20a
MDW
10:18a
6h 58m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Wed Aug 12 2015 Return: Fri Aug 14 2015 Trip spans 3 days
Delta
Delta
MCO
5:30a
MDW
10:18a
4h 48m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Thu Aug 13 2015 Return: Mon Aug 17 2015 Trip spans 5 days
Delta
Delta
MCO
10:11a
MDW
2:53p
4h 42m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Sat Aug 15 2015 Return: Mon Aug 24 2015 Trip spans 10 days
Delta
Delta
MCO
9:22a
MDW
2:35p
5h 13m
1 stop
MDW
8:19a
MCO
12:27p
4h 08m
1 stop
Depart: Tue Aug 18 2015 Return: Wed Aug 19 2015 Trip spans 2 days
Delta
Delta
MCO
9:30a
MDW
2:22p
4h 52m
1 stop
MDW
3:10a
MCO
7:26a
4h 16m
1 stop
Depart: Wed Aug 19 2015 Return: Mon Aug 24 2015 Trip spans 6 days
Delta
Delta
MCO
11:30a
MDW
3:57p
4h 27m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Sat Aug 22 2015 Return: Mon Aug 24 2015 Trip spans 3 days
Delta
Delta
MCO
10:30a
MDW
5:15p
6h 45m
1 stop
MDW
8:31a
MCO
3:26p
6h 55m
1 stop
Depart: Sun Aug 23 2015 Return: Mon Aug 24 2015 Trip spans 2 days
Delta
Delta
MCO
1:20a
MDW
6:12a
4h 52m
1 stop
MDW
1:57p
MCO
6:26p
4h 29m
1 stop
Depart: Mon Aug 24 2015 Return: Tue Aug 25 2015 Trip spans 2 days
Delta
Delta
MCO
3:20a
MDW
10:05a
6h 45m
1 stop
MDW
1:57p
MCO
7:35p
5h 38m
1 stop
Depart: Tue Aug 25 2015 Return: Fri Aug 28 2015 Trip spans 4 days
Delta
Delta
MCO
3:20a
MDW
8:44a
5h 24m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Wed Aug 26 2015 Return: Fri Aug 28 2015 Trip spans 3 days
Delta
Delta
MCO
10:05a
MDW
2:55p
4h 50m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Thu Aug 27 2015 Return: Fri Aug 28 2015 Trip spans 2 days
Delta
Delta
MCO
5:30a
MDW
10:05a
4h 35m
1 stop
MDW
9:40a
MCO
2:35p
4h 55m
1 stop
Depart: Thu Aug 20 2015 Return: Mon Aug 24 2015 Trip spans 5 days
Delta
Delta
MCO
4:20a
MDW
11:53a
7h 33m
1 stop
MDW
12:33p
MCO
5:09p
4h 36m
1 stop
Depart: Fri Aug 21 2015 Return: Mon Aug 24 2015 Trip spans 4 days
Delta
Delta
MCO
3:00a
MDW
9:23a
6h 23m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Fri Aug 28 2015 Return: Sun Aug 30 2015 Trip spans 3 days
Delta
Delta
MCO
1:20a
MDW
6:12a
4h 52m
1 stop
MDW
3:10a
MCO
9:23a
6h 13m
1 stop
Depart: Sat Aug 29 2015 Return: Mon Aug 31 2015 Trip spans 3 days
Delta
Delta
MCO
9:30a
MDW
2:43p
5h 13m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Select an airline:  Southwest
Direct flights MCO to MDW on Southwest
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1709 6:35 am 8:20 am Jul 25 - Aug 8
2135 6:45 am 8:35 am Aug 10 - Sep 4
1531 6:50 am 8:35 am Jul 27 - Aug 7
4594 8:25 am 10:15 am Aug 15 - Aug 29
4321 8:50 am 10:30 am Jul 26 - Aug 7
4321 8:50 am 10:30 am Jul 25 - Aug 8
1025 10:05 am 11:45 am Aug 8 - Aug 8
3914 10:10 am 11:55 am Aug 15 - Aug 29
917 10:45 am 12:25 pm Jul 27 - Aug 7
2650 11:20 am 1:05 pm Jul 25 - Aug 8
4543 11:30 am 1:15 pm Aug 15 - Aug 29
1146 11:45 am 1:30 pm Aug 9 - Sep 25
174 12:10 pm 1:55 pm Jul 27 - Aug 7
718 12:25 pm 2:10 pm Aug 8 - Aug 8
1526 12:35 pm 2:20 pm Aug 15 - Aug 29
50 12:50 pm 2:35 pm Aug 9 - Sep 4
693 1:40 pm 3:30 pm Aug 15 - Aug 29
4229 1:55 pm 3:40 pm Jul 25 - Aug 8
1344 2:10 pm 3:55 pm Jul 27 - Aug 7
4052 2:40 pm 4:30 pm Aug 15 - Aug 29
1660 3:15 pm 5:00 pm Jul 25 - Aug 8
136 3:20 pm 5:10 pm Aug 24 - Aug 24
136 3:20 pm 5:10 pm Aug 17 - Aug 23
136 3:20 pm 5:10 pm Aug 9 - Aug 16
136 3:20 pm 5:10 pm Aug 25 - Sep 4
136 3:20 pm 5:10 pm Aug 10 - Aug 10
316 4:00 pm 5:50 pm Aug 15 - Aug 29
568 4:00 pm 5:45 pm Jul 26 - Aug 7
1167 4:15 pm 6:05 pm Aug 8 - Aug 8
2095 5:10 pm 7:00 pm Aug 9 - Sep 4
1624 5:30 pm 7:20 pm Aug 15 - Aug 29
1506 6:05 pm 7:50 pm Jul 26 - Aug 7
6366 6:45 pm 8:35 pm Aug 8 - Aug 8
566 6:50 pm 8:40 pm Aug 10 - Sep 4
1496 7:00 pm 8:50 pm Aug 9 - Aug 30
895 7:15 pm 9:10 pm Jul 26 - Aug 7
153 7:20 pm 9:10 pm Aug 8 - Aug 8
246 8:50 pm 10:40 pm Aug 9 - Sep 4
1463 10:25 pm 12:05 am Aug 2 - Aug 7
Airports
Origin

Orlando
$186
Destination

Chicago
$186
Airlines