Cheap Flights from Orlando to Chicago (ORL - 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

Best fares from ORL to MDW

Sun Mon Tue Wed Thu Fri Sat
  1 $496 2 $384 3 $321 4 $321 5 $321 6 $321
7 $376 8 $321 9 $272 10 $272 11 $272 12 $272 13 $277
14 $339 15 $271 16 $434 17 $282 18 $300 19 $302 20 $286
21 $347 22 $282 23 $282 24 $277 25 $277 26 $295 27 $321
28 $328 29 $295 30 $321 31 $315      

Best fares found by others...

KAYAK searches hundreds of sites to find the best rate for your next flight from Orlando to Chicago. Get the best flight deal for your Chicago trip!
Here's how it works. Search KAYAK for a flight ticket from Orlando to Chicago. Sort, filter and compare results on one web page. Then book your plane ticket direct on the airline or travel agent site of your choice!
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
137 7:15 am 9:15 am Jan 5 - Jan 5
244 7:15 am 9:15 am Dec 29 - Jan 4
4134 7:15 am 9:10 am Dec 26 - Dec 26
4134 7:15 am 9:10 am Dec 2 - Dec 23
963 7:15 am 9:15 am Jan 1 - Jan 1
2647 7:20 am 9:10 am Dec 20 - Dec 27
2647 7:20 am 9:10 am Dec 28 - Dec 28
1463 7:25 am 9:20 am Dec 6 - Dec 13
2413 9:05 am 10:55 am Dec 24 - Dec 24
1986 9:20 am 11:10 am Dec 7 - Dec 19
1986 9:20 am 11:10 am Nov 29 - Dec 5
1986 9:20 am 11:10 am Dec 20 - Dec 28
1849 9:25 am 11:15 am Dec 29 - Jan 5
4877 10:25 am 12:25 pm Dec 31 - Dec 31
1490 10:40 am 12:30 pm Dec 25 - Dec 25
4294 11:45 am 1:40 pm Dec 6 - Dec 13
1253 12:05 pm 1:55 pm Jan 4 - Jan 4
1253 12:05 pm 1:55 pm Jan 3 - Jan 3
277 12:05 pm 1:55 pm Jan 1 - Jan 1
277 12:05 pm 1:55 pm Dec 29 - Jan 5
1560 12:30 pm 2:20 pm Dec 28 - Dec 28
1560 12:30 pm 2:20 pm Dec 20 - Dec 27
2165 12:35 pm 2:25 pm Dec 24 - Dec 25
4139 12:35 pm 2:25 pm Dec 26 - Dec 26
4139 12:35 pm 2:25 pm Dec 7 - Dec 23
4139 12:35 pm 2:25 pm Nov 27 - Dec 5
3332 1:45 pm 3:35 pm Dec 31 - Dec 31
1452 1:55 pm 3:45 pm Dec 24 - Dec 24
4136 2:05 pm 3:55 pm Dec 25 - Dec 25
4508 2:05 pm 3:55 pm Dec 2 - Dec 23
4508 2:05 pm 3:55 pm Dec 26 - Dec 26
1502 2:15 pm 4:05 pm Dec 6 - Dec 13
4136 2:20 pm 4:10 pm Dec 28 - Dec 28
4136 2:20 pm 4:10 pm Dec 20 - Dec 27
2593 3:10 pm 5:00 pm Dec 2 - Dec 23
2593 3:10 pm 5:00 pm Dec 25 - Dec 25
2593 3:10 pm 5:00 pm Dec 26 - Dec 26
2593 3:10 pm 5:00 pm Dec 24 - Dec 24
939 3:10 pm 5:00 pm Dec 20 - Dec 27
939 3:10 pm 5:00 pm Dec 28 - Dec 28
4250 3:35 pm 5:30 pm Dec 6 - Dec 13
683 3:35 pm 5:30 pm Jan 5 - Jan 5
683 3:35 pm 5:30 pm Dec 29 - Jan 2
1341 3:40 pm 5:35 pm Jan 1 - Jan 1
2264 3:40 pm 5:35 pm Jan 3 - Jan 3
2264 3:40 pm 5:35 pm Jan 4 - Jan 4
604 4:25 pm 6:15 pm Jan 5 - Jan 5
631 4:25 pm 6:15 pm Dec 24 - Dec 24
671 4:25 pm 6:15 pm Dec 20 - Dec 28
671 4:25 pm 6:15 pm Dec 2 - Dec 19
698 4:25 pm 6:15 pm Dec 25 - Dec 25
1139 4:35 pm 6:25 pm Jan 3 - Jan 3
2024 4:35 pm 6:25 pm Dec 29 - Jan 2
412 4:35 pm 6:25 pm Jan 4 - Jan 4
4460 4:45 pm 6:35 pm Dec 6 - Dec 13
2896 5:55 pm 7:50 pm Dec 31 - Dec 31
1680 6:15 pm 8:05 pm Dec 6 - Dec 13
502 6:25 pm 8:15 pm Dec 24 - Dec 24
127 7:05 pm 8:55 pm Dec 31 - Dec 31
127 7:05 pm 8:55 pm Jan 5 - Jan 5
127 7:05 pm 8:55 pm Dec 29 - Jan 4
4318 7:20 pm 9:10 pm Dec 26 - Dec 26
4318 7:20 pm 9:10 pm Dec 2 - Dec 23
4604 7:20 pm 9:10 pm Dec 6 - Dec 13
1009 7:25 pm 9:15 pm Dec 25 - Dec 25
1827 7:30 pm 9:20 pm Dec 20 - Dec 27
1827 7:30 pm 9:20 pm Dec 28 - Dec 28
1341 8:05 pm 9:55 pm Dec 6 - Dec 13
521 8:05 pm 9:55 pm Jan 1 - Jan 1
521 8:05 pm 9:55 pm Dec 31 - Dec 31
1456 8:55 pm 10:45 pm Dec 24 - Dec 24
2151 9:00 pm 10:50 pm Dec 29 - Jan 4
1401 9:05 pm 10:55 pm Dec 25 - Dec 25
491 9:10 pm 11:00 pm Jan 5 - Jan 5
1186 9:15 pm 11:05 pm Dec 7 - Dec 19
1186 9:15 pm 11:05 pm Nov 28 - Dec 5
1186 9:15 pm 11:05 pm Dec 20 - Dec 28
2655 9:30 pm 11:20 pm Dec 31 - Dec 31
1622 9:50 pm 11:40 pm Jan 1 - Jan 1
470 10:00 pm 11:50 pm Dec 29 - Jan 5