Find Deals on Flights from Orlando to Chicago Midway (MCO - 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.
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: Wed Mar 2 2016 Return: Mon Mar 14 2016 Trip spans 12 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 3 2016 Return: Sun Mar 6 2016 Trip spans 4 days
Delta
Delta
MCO
1:20a
MDW
5:34a
4h 14m
1 stop
MDW
2:05a
MCO
7:20a
5h 15m
1 stop
Depart: Fri Mar 4 2016 Return: Sun Mar 6 2016 Trip spans 3 days
Delta
Delta
MCO
7:20a
MDW
3:05p
7h 45m
1 stop
MDW
1:20p
MCO
5:40p
4h 20m
1 stop
Depart: Sat Mar 5 2016 Return: Sun Mar 6 2016 Trip spans 2 days
Delta
Delta
MCO
9:20a
MDW
5:30p
8h 10m
1 stop
MDW
11:35a
MCO
4:33p
4h 58m
1 stop
Depart: Sun Mar 6 2016 Return: Mon Mar 14 2016 Trip spans 8 days
Delta
Delta
MCO
3:21a
MDW
8:22a
5h 01m
1 stop
MDW
1:06p
MCO
7:06p
6h 00m
1 stop
Depart: Mon Mar 7 2016 Return: Mon Mar 14 2016 Trip spans 7 days
Delta
Delta
MCO
1:10a
MDW
8:22a
7h 12m
1 stop
MDW
8:15a
MCO
1:26p
5h 11m
1 stop
Depart: Tue Mar 8 2016 Return: Wed Mar 9 2016 Trip spans 2 days
Delta
Delta
MCO
9:25a
MDW
4:28p
7h 03m
1 stop
MDW
9:00a
MCO
3:02p
6h 02m
1 stop
Depart: Wed Mar 9 2016 Return: Mon Mar 14 2016 Trip spans 5 days
Delta
Delta
MCO
11:00a
MDW
4:10p
5h 10m
1 stop
MDW
1:06p
MCO
7:06p
6h 00m
1 stop
Depart: Thu Mar 10 2016 Return: Tue Mar 15 2016 Trip spans 5 days
Delta
Delta
MCO
1:20a
MDW
5:34a
4h 14m
1 stop
MDW
8:15a
MCO
12:23p
4h 08m
1 stop
Depart: Fri Mar 11 2016 Return: Mon Mar 14 2016 Trip spans 3 days
Delta
Delta
MCO
3:20a
MDW
7:39a
4h 19m
1 stop
MDW
6:10a
MCO
1:26p
7h 16m
1 stop
Depart: Sat Mar 12 2016 Return: Tue Mar 15 2016 Trip spans 3 days
Delta
Delta
MCO
1:20a
MDW
5:33a
4h 13m
1 stop
MDW
6:10a
MCO
10:24a
4h 14m
1 stop
Depart: Tue Mar 15 2016 Return: Wed Mar 16 2016 Trip spans 2 days
Delta
Delta
MCO
2:20a
MDW
6:34a
4h 14m
1 stop
MDW
8:15a
MCO
1:26p
5h 11m
1 stop
Depart: Tue Apr 12 2016 Return: Wed Apr 20 2016 Trip spans 9 days
Delta
Delta
MCO
10:25a
MDW
2:44p
4h 19m
1 stop
MDW
11:35a
MCO
3:57p
4h 22m
1 stop
Depart: Thu Feb 18 2016 Return: Thu Mar 3 2016 Trip spans 15 days
Delta
Delta
MCO
12:15a
MDW
5:35a
5h 20m
1 stop
MDW
5:10a
MCO
12:26p
7h 16m
1 stop
Depart: Fri Feb 19 2016 Return: Thu Mar 3 2016 Trip spans 14 days
Delta
Delta
MCO
4:28a
MDW
12:46p
8h 18m
1 stop
MDW
2:05a
MCO
6:24a
4h 19m
1 stop
Depart: Sat Feb 20 2016 Return: Thu Mar 3 2016 Trip spans 13 days
Delta
Delta
MCO
4:28a
MDW
10:40a
6h 12m
1 stop
MDW
4:09a
MCO
11:19a
7h 10m
1 stop
Depart: Sun Feb 21 2016 Return: Thu Mar 3 2016 Trip spans 12 days
Delta
Delta
MCO
6:32a
MDW
12:46p
6h 14m
1 stop
MDW
7:15a
MCO
12:26p
5h 11m
1 stop
Depart: Mon Feb 22 2016 Return: Thu Mar 3 2016 Trip spans 11 days
Delta
Delta
MCO
4:28a
MDW
12:46p
8h 18m
1 stop
MDW
5:10a
MCO
11:23a
6h 13m
1 stop
Depart: Tue Feb 23 2016 Return: Thu Mar 3 2016 Trip spans 10 days
Delta
Delta
MCO
6:32a
MDW
3:06p
8h 34m
1 stop
MDW
1:00a
MCO
6:24a
5h 24m
1 stop
Depart: Wed Feb 24 2016 Return: Thu Mar 3 2016 Trip spans 9 days
Delta
Delta
MCO
5:30a
MDW
9:46a
4h 16m
1 stop
MDW
7:15a
MCO
11:23a
4h 08m
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
2177 6:55 am 8:45 am Mar 14 - Apr 11
2177 6:55 am 8:45 am Mar 10 - Mar 11
2177 6:55 am 8:45 am Mar 13 - Apr 10
4499 7:25 am 9:15 am Mar 19 - Apr 9
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
4179 8:05 am 9:55 am Mar 19 - Apr 9
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
4124 8:45 am 10:35 am Mar 19 - Apr 9
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 13 - Apr 11
1117 10:05 am 11:55 am Mar 10 - Mar 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
4463 11:05 am 12:55 pm Mar 19 - Apr 9
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 19 - Apr 9
424 11:50 am 1:40 pm Mar 12 - Mar 12
1594 12:20 pm 2:10 pm Mar 12 - Mar 12
1594 12:20 pm 2:10 pm Mar 19 - Apr 9
1075 12:30 pm 2:20 pm Feb 27 - Mar 5
1075 12:30 pm 2:20 pm Feb 20 - Feb 20
699 1:05 pm 2:55 pm Mar 13 - Apr 11
699 1:05 pm 2:55 pm Mar 10 - Mar 11
1959 2:20 pm 4:10 pm Jan 30 - Mar 5
2253 2:35 pm 4:25 pm Mar 12 - Mar 12
2253 2:35 pm 4:25 pm Mar 19 - Apr 9
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 19 - Apr 9
2590 3:10 pm 5:00 pm Mar 12 - Mar 12
1723 3:15 pm 5:10 pm Feb 8 - Feb 26
1723 3:15 pm 5:10 pm Feb 28 - Mar 4
1723 3:15 pm 5:10 pm Mar 6 - Mar 8
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
2935 4:40 pm 6:30 pm Mar 19 - Apr 9
4574 5:10 pm 7:00 pm Mar 19 - Apr 9
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 10 - Mar 11
4258 5:50 pm 7:40 pm Mar 13 - Apr 11
806 6:20 pm 8:10 pm Mar 12 - Mar 12
806 6:20 pm 8:10 pm Mar 19 - Apr 9
1331 6:25 pm 8:20 pm Jan 30 - Mar 5
536 7:05 pm 8:55 pm Mar 12 - Mar 12
536 7:05 pm 8:55 pm Mar 19 - Mar 19
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 19 - Apr 9
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.

We aggregate tons of data for you
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 don'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.

More questions or if you have a bad price to report to us
Please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Orlando
$214
Destination

Chicago
$214
Airlines