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: Fri Mar 3 2017 Return: Sun Mar 5 2017 Trip spans 3 days
Delta
Delta
MCO
12:15a
MDW
5:53a
5h 38m
1 stop
MDW
1:30p
MCO
6:57p
5h 27m
1 stop
Depart: Sat Mar 4 2017 Return: Sun Mar 5 2017 Trip spans 2 days
Delta
Delta
MCO
9:30a
MDW
4:43p
7h 13m
1 stop
MDW
1:30p
MCO
6:57p
5h 27m
1 stop
Depart: Sun Mar 5 2017 Return: Mon Mar 6 2017 Trip spans 2 days
Delta
Delta
MCO
1:10a
MDW
8:33a
7h 23m
1 stop
MDW
12:29p
MCO
6:41p
6h 12m
1 stop
Depart: Tue Mar 7 2017 Return: Wed Mar 8 2017 Trip spans 2 days
Delta
Delta
MCO
1:30a
MDW
5:53a
4h 23m
1 stop
MDW
7:29a
MCO
3:04p
7h 35m
1 stop
Depart: Wed Mar 8 2017 Return: Mon Mar 13 2017 Trip spans 5 days
Delta
Delta
MCO
1:30a
MDW
5:53a
4h 23m
1 stop
MDW
11:53a
MCO
4:43p
4h 50m
1 stop
Depart: Thu Mar 9 2017 Return: Mon Mar 13 2017 Trip spans 4 days
Delta
Delta
MCO
3:30a
MDW
8:28a
4h 58m
1 stop
MDW
2:00p
MCO
7:02p
5h 02m
1 stop
Depart: Fri Mar 10 2017 Return: Mon Mar 13 2017 Trip spans 3 days
Delta
Delta
MCO
1:20p
MDW
6:10p
4h 50m
1 stop
MDW
12:35p
MCO
6:09p
5h 34m
1 stop
Depart: Sat Mar 11 2017 Return: Mon Mar 13 2017 Trip spans 2 days
Delta
Delta
MCO
1:20a
MDW
5:43a
4h 23m
1 stop
MDW
9:48a
MCO
3:30p
5h 42m
1 stop
Depart: Tue Mar 14 2017 Return: Wed Mar 15 2017 Trip spans 2 days
Delta
Delta
MCO
3:50a
MDW
8:14a
4h 24m
1 stop
MDW
2:00p
MCO
7:02p
5h 02m
1 stop
Depart: Wed Mar 15 2017 Return: Mon Mar 20 2017 Trip spans 6 days
Delta
Delta
MCO
3:20a
MDW
10:07a
6h 47m
1 stop
MDW
2:45p
MCO
7:34p
4h 49m
1 stop
Depart: Thu Mar 16 2017 Return: Mon Mar 20 2017 Trip spans 5 days
Delta
Delta
MCO
2:15a
MDW
9:28a
7h 13m
1 stop
MDW
2:45p
MCO
7:34p
4h 49m
1 stop
Depart: Tue Mar 21 2017 Return: Mon Mar 27 2017 Trip spans 7 days
Delta
Delta
MCO
3:50a
MDW
10:07a
6h 17m
1 stop
MDW
2:00p
MCO
7:58p
5h 58m
1 stop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
Delta
Delta
MCO
8:25a
MDW
2:25p
6h 00m
1 stop
MDW
2:00p
MCO
7:58p
5h 58m
1 stop
Depart: Thu Mar 23 2017 Return: Mon Mar 27 2017 Trip spans 5 days
Delta
Delta
MCO
2:20a
MDW
6:43a
4h 23m
1 stop
MDW
2:00p
MCO
7:02p
5h 02m
1 stop
Depart: Tue Mar 28 2017 Return: Mon Apr 3 2017 Trip spans 7 days
Delta
Delta
MCO
5:24a
MDW
11:42a
6h 18m
1 stop
MDW
1:55p
MCO
7:58p
6h 03m
1 stop
Depart: Wed Mar 29 2017 Return: Mon Apr 3 2017 Trip spans 6 days
Delta
Delta
MCO
4:20a
MDW
10:07a
5h 47m
1 stop
MDW
1:55p
MCO
7:58p
6h 03m
1 stop
Depart: Wed Apr 5 2017 Return: Mon Apr 10 2017 Trip spans 6 days
Delta
Delta
MCO
2:20a
MDW
8:48a
6h 28m
1 stop
MDW
8:59a
MCO
3:18p
6h 19m
1 stop
Depart: Wed Apr 12 2017 Return: Tue Apr 18 2017 Trip spans 7 days
Delta
Delta
MCO
3:50a
MDW
8:48a
4h 58m
1 stop
MDW
10:08a
MCO
3:24p
5h 16m
1 stop
Depart: Thu Apr 13 2017 Return: Mon Apr 17 2017 Trip spans 5 days
Delta
Delta
MCO
3:00a
MDW
8:47a
5h 47m
1 stop
MDW
11:52a
MCO
5:35p
5h 43m
1 stop
Depart: Thu Apr 20 2017 Return: Tue Apr 25 2017 Trip spans 6 days
Delta
Delta
MCO
3:00a
MDW
8:47a
5h 47m
1 stop
MDW
10:08a
MCO
5:35p
7h 27m
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
1129 6:55 am 8:45 am Mar 9 - Mar 9
1129 7:00 am 8:50 am Mar 13 - Apr 24
1129 7:00 am 8:50 am Mar 10 - Mar 10
4289 7:30 am 9:20 am Mar 18 - Apr 22
4289 7:30 am 9:20 am Mar 11 - Mar 11
6559 7:50 am 9:40 am Mar 12 - Apr 23
4693 9:00 am 10:50 am Feb 16 - Mar 8
1783 9:20 am 11:10 am Mar 13 - Apr 24
1783 9:20 am 11:10 am Mar 10 - Mar 10
1783 9:20 am 11:10 am Mar 9 - Mar 9
5566 9:20 am 11:05 am Mar 25 - Apr 1
4480 9:40 am 11:25 am Mar 11 - Mar 11
4480 9:40 am 11:25 am Mar 18 - Mar 18
4918 9:45 am 11:35 am Feb 19 - Mar 5
1108 10:50 am 12:40 pm Feb 16 - Mar 8
4745 10:50 am 12:40 pm Mar 12 - Apr 23
889 10:55 am 12:45 pm Mar 11 - Mar 11
889 10:55 am 12:45 pm Mar 18 - Apr 22
1788 11:10 am 1:00 pm Mar 13 - Apr 21
1788 11:10 am 1:00 pm Mar 10 - Mar 10
1788 11:15 am 1:05 pm Mar 9 - Mar 9
2566 11:25 am 1:15 pm Feb 18 - Mar 4
2242 11:40 am 1:30 pm Mar 18 - Apr 22
2242 11:40 am 1:30 pm Mar 11 - Mar 11
4480 11:40 am 1:35 pm Feb 19 - Mar 5
4015 11:55 am 1:45 pm Mar 12 - Apr 23
4695 12:05 pm 2:00 pm Feb 16 - Mar 8
2781 12:50 pm 2:40 pm Mar 18 - Apr 22
2781 12:50 pm 2:40 pm Mar 11 - Mar 11
5735 1:05 pm 2:55 pm Mar 12 - Apr 23
3980 2:15 pm 4:05 pm Mar 9 - Mar 10
3980 2:15 pm 4:05 pm Mar 13 - Apr 24
5892 2:30 pm 4:25 pm Feb 18 - Mar 4
3158 3:00 pm 4:50 pm Mar 12 - Apr 23
3059 3:05 pm 5:00 pm Feb 19 - Mar 5
1123 3:15 pm 5:05 pm Mar 13 - Apr 24
1123 3:15 pm 5:05 pm Mar 11 - Mar 11
1123 3:15 pm 5:05 pm Mar 18 - Apr 22
1123 3:15 pm 5:05 pm Mar 9 - Mar 10
4425 4:30 pm 6:20 pm Mar 13 - Apr 24
4425 4:30 pm 6:20 pm Mar 9 - Mar 10
1465 4:35 pm 6:30 pm Feb 19 - Mar 5
1465 4:35 pm 6:30 pm Feb 18 - Mar 4
1834 4:40 pm 6:30 pm Feb 16 - Mar 8
5161 4:45 pm 6:35 pm Mar 11 - Mar 11
5161 4:45 pm 6:35 pm Mar 18 - Apr 22
4405 4:55 pm 6:45 pm Mar 12 - Apr 23
690 5:25 pm 7:20 pm Mar 11 - Mar 11
690 5:25 pm 7:20 pm Mar 18 - Apr 22
2509 5:40 pm 7:35 pm Feb 18 - Mar 4
529 5:45 pm 7:35 pm Feb 16 - Mar 8
5874 5:45 pm 7:30 pm Mar 20 - Apr 7
2245 6:10 pm 8:00 pm Mar 11 - Mar 11
2245 6:10 pm 8:00 pm Mar 18 - Apr 22
4649 6:30 pm 8:20 pm Feb 19 - Mar 5
4715 6:45 pm 8:35 pm Mar 11 - Mar 11
4715 6:45 pm 8:35 pm Mar 18 - Apr 22
1102 7:10 pm 9:00 pm Feb 18 - Mar 4
2796 7:30 pm 9:20 pm Mar 18 - Apr 22
2796 7:30 pm 9:20 pm Mar 11 - Mar 11
4316 7:30 pm 9:20 pm Feb 16 - Mar 8
4859 7:40 pm 9:30 pm Mar 13 - Apr 24
4859 7:40 pm 9:30 pm Mar 9 - Mar 10
2458 8:20 pm 10:10 pm Feb 18 - Mar 4
234 8:30 pm 10:20 pm Mar 11 - Mar 11
234 8:30 pm 10:20 pm Mar 18 - Apr 22
4679 8:35 pm 10:25 pm Feb 20 - Mar 8
3229 8:45 pm 10:35 pm Feb 19 - Mar 5
6069 9:00 pm 10:45 pm Mar 12 - Apr 23
2071 9:40 pm 11:25 pm Mar 18 - Apr 22
2071 9:40 pm 11:25 pm Mar 11 - Mar 11
4270 10:00 pm 11:45 pm Mar 12 - Apr 23
1854 10:10 pm 11:55 pm Mar 13 - Apr 24
1854 10:10 pm 11:55 pm Mar 10 - Mar 10
2797 10:15 pm 12:05 am Feb 19 - Mar 5
1854 10:20 pm 12:05 am Mar 9 - Mar 9
6275 10:30 pm 12:15 am Mar 18 - Apr 22
6275 10:30 pm 12:15 am Mar 11 - Mar 11
3483 10:55 pm 12:40 am Mar 12 - Apr 23
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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
$194
Destination

Chicago
$194
Airlines