Orlando to Chicago
MCOMDW
Fly from Orlando to Chicago starting at USD 80 with NK.
Best fare available on May 29, 2026.
Limited seats. Better plans. Book before it's gone.
Orlando to Chicago cheapest flights this week
10 May
F9
07:40MCO
15:12MDW
1 Stop$134VIEW DEAL
22 May
G4
11:24MCO
21:33MDW
1 Stop$169VIEW DEAL
24 May
WN
20:55MCO
23:45MDW
Direct$107VIEW DEAL
29 May
NK
22:44MCO
23:02MDW
1 Stop$80VIEW DEAL
4 Jun
WN
07:25MCO
10:15MDW
Direct$98VIEW DEAL
5 Jun
F9
17:10MCO
23:02MDW
1 Stop$110VIEW DEAL
Orlando to Chicago monthly flight fare trend
May
from USD 76
Jun
from USD 98
Jul
No flights
Aug
No flights
Sep
No flights
Oct
No flights
Airport Details
Origin
Orlando
Orlando International Airport (MCO)
Orlando, MCO
Zone
New York
Elev
96 ft
Destination
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
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