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.
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Book cheap flights from Orlando to Chicago Midway

(Round-trip)
Depart: Wed May 11 2016 Return: Tue May 17 2016 Trip spans 7 days
Depart: Mon Jun 6 2016 Return: Wed Jun 8 2016 Trip spans 3 days
Depart: Fri May 27 2016 Return: Mon May 30 2016 Trip spans 4 days
Depart: Sat May 14 2016 Return: Wed May 18 2016 Trip spans 5 days
Depart: Tue Nov 15 2016 Return: Mon Nov 21 2016 Trip spans 7 days
Depart: Tue May 17 2016 Return: Tue May 24 2016 Trip spans 8 days
Depart: Wed May 18 2016 Return: Tue May 24 2016 Trip spans 7 days
Depart: Fri Jun 10 2016 Return: Mon Jun 27 2016 Trip spans 18 days
Depart: Thu May 19 2016 Return: Tue May 24 2016 Trip spans 6 days
Depart: Fri Jul 22 2016 Return: Tue Jul 26 2016 Trip spans 5 days
Depart: Sat May 21 2016 Return: Tue May 24 2016 Trip spans 4 days
Depart: Fri Oct 21 2016 Return: Mon Oct 24 2016 Trip spans 4 days
Depart: Mon May 23 2016 Return: Sat May 28 2016 Trip spans 6 days
Depart: Tue May 24 2016 Return: Wed May 25 2016 Trip spans 2 days
Depart: Wed May 25 2016 Return: Sat May 28 2016 Trip spans 4 days
Depart: Wed Jun 1 2016 Return: Mon Jun 6 2016 Trip spans 6 days
Depart: Sat Jun 4 2016 Return: Mon Jun 6 2016 Trip spans 3 days
Depart: Sun Jun 5 2016 Return: Mon Jun 6 2016 Trip spans 2 days
Depart: Tue Jun 7 2016 Return: Wed Jun 8 2016 Trip spans 2 days
Depart: Wed Jun 8 2016 Return: Mon Jun 13 2016 Trip spans 6 days
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
2184 7:05 am 8:50 am May 31 - Jun 3
2184 7:05 am 8:50 am Apr 28 - May 27
3468 7:25 am 9:05 am Jun 6 - Jul 1
5774 7:30 am 9:10 am Jun 11 - Aug 6
6225 7:35 am 9:20 am May 30 - May 30
2730 7:50 am 9:45 am May 29 - May 29
136 8:20 am 10:00 am Jun 5 - Jul 1
2170 8:25 am 10:10 am Apr 30 - Jun 4
525 9:10 am 10:50 am Jun 11 - Jul 30
6556 9:25 am 11:05 am Jun 5 - Jun 26
418 9:45 am 11:30 am Jun 4 - Jun 4
418 9:45 am 11:30 am May 28 - May 28
418 9:45 am 11:30 am Apr 30 - May 21
3599 10:25 am 12:05 pm Jun 5 - Jul 1
3975 11:00 am 12:45 pm May 30 - May 30
413 11:00 am 12:45 pm Apr 28 - May 27
413 11:00 am 12:45 pm May 31 - Jun 3
1249 11:05 am 12:50 pm May 29 - May 29
639 11:05 am 12:45 pm Jun 11 - Jul 30
2659 11:50 am 1:35 pm May 28 - May 28
2808 11:50 am 1:35 pm Jun 4 - Jun 4
2808 11:50 am 1:35 pm Apr 30 - May 21
1356 12:05 pm 1:50 pm Jun 5 - Jul 1
6218 12:15 pm 2:00 pm Jun 11 - Jul 30
1209 12:35 pm 2:20 pm May 29 - May 29
1797 12:35 pm 2:20 pm May 31 - Jun 3
1797 12:35 pm 2:20 pm Apr 28 - May 27
5966 12:35 pm 2:20 pm May 30 - May 30
3791 12:40 pm 2:25 pm Apr 30 - Jun 4
5450 1:30 pm 3:15 pm Jun 11 - Jun 25
1756 2:05 pm 3:50 pm Apr 28 - May 27
1756 2:05 pm 3:50 pm May 31 - Jun 3
6366 2:05 pm 3:50 pm May 29 - May 30
2005 2:10 pm 3:55 pm Jun 5 - Jul 1
3996 3:10 pm 5:00 pm Jun 11 - Jul 30
2451 3:30 pm 5:15 pm Apr 30 - May 21
2451 3:30 pm 5:15 pm Jun 4 - Jun 4
9 3:30 pm 5:15 pm May 28 - May 28
2157 4:00 pm 5:50 pm Jun 11 - Aug 6
1422 4:10 pm 6:00 pm Jun 5 - Jul 1
105 4:20 pm 6:05 pm Jun 4 - Jun 4
37 4:20 pm 6:05 pm Apr 30 - May 28
544 4:40 pm 6:30 pm Jun 11 - Jul 2
5860 5:25 pm 7:10 pm Jun 11 - Aug 6
1167 5:40 pm 7:25 pm Jun 5 - Jul 1
4150 5:50 pm 7:35 pm May 28 - May 28
518 5:50 pm 7:35 pm Jun 4 - Jun 4
518 5:50 pm 7:35 pm Apr 30 - May 21
2356 6:20 pm 8:05 pm May 29 - May 30
3332 6:20 pm 8:05 pm May 31 - Jun 3
3332 6:20 pm 8:05 pm Apr 28 - May 27
5256 6:45 pm 8:30 pm May 1 - May 22
3610 7:05 pm 8:55 pm Apr 30 - Jun 4
1787 7:15 pm 9:00 pm May 29 - May 29
6233 7:15 pm 9:05 pm Jun 11 - Aug 6
1768 7:30 pm 9:15 pm Apr 28 - May 27
1768 7:30 pm 9:15 pm May 31 - Jun 3
5942 7:30 pm 9:15 pm May 30 - May 30
1480 8:40 pm 10:30 pm Jun 5 - Jul 1
2494 9:15 pm 11:00 pm May 28 - May 28
2494 9:55 pm 11:40 pm Apr 30 - May 21
2494 9:55 pm 11:40 pm Jun 4 - Jun 4
556 10:00 pm 11:40 pm May 29 - May 29
556 10:00 pm 11:40 pm May 22 - May 27
556 10:00 pm 11:40 pm May 31 - Jun 3
556 10:00 pm 11:40 pm May 30 - May 30
556 10:00 pm 11:40 pm Apr 28 - May 20
5076 10:25 pm 12:05 am Jun 11 - Aug 6
556 10:30 pm 12:10 am Jun 5 - Jul 1
* 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
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Airports
Origin

Orlando
$214
Destination

Chicago
$214