Chicago to Orlando
MDWMCO
Fly from Chicago to Orlando starting at USD 71 with F9.
Best fare available on May 20, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to Orlando cheapest flights this week
13 May
F9
06:00MDW
13:15MCO
1 Stop$76VIEW DEAL
15 May
F9
12:04MDW
20:47MCO
1 Stop$78VIEW DEAL
17 May
WN
20:50MDW
23:25MCO
Direct$134VIEW DEAL
20 May
F9
15:07MDW
23:10MCO
1 Stop$71VIEW DEAL
22 May
F9
15:07MDW
22:21MCO
1 Stop$134VIEW DEAL
2 Jun
F9
12:27MDW
18:32MCO
1 Stop$73VIEW DEAL
8 Jun
F9
06:00MDW
16:18MCO
1 Stop$128VIEW DEAL
17 Jul
F9
12:04MDW
18:40MCO
1 Stop$100VIEW DEAL
Chicago to Orlando monthly flight fare trend
May
from USD 55
Jun
from USD 73
Jul
from USD 100
Aug
No flights
Sep
No flights
Oct
No flights
Airport Details
Origin
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
Destination
Orlando
Orlando International Airport (MCO)
Orlando, MCO
Zone
New York
Elev
96 ft
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