Chicago to Orlando

MDWMCO

Fly from Chicago to Orlando starting at USD 123 with Southwest Airlines.Best fare available on Sep 16, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Orlando cheapest flights this week

10 Sept
Frontier Airlines
06:25MDW
16:09MCO
1 StopUSD 125VIEW DEAL
11 Sept
Frontier Airlines
06:25MDW
16:09MCO
1 StopUSD 129VIEW DEAL
13 Sept
Frontier Airlines
06:25MDW
16:09MCO
1 StopUSD 174VIEW DEAL
14 Sept
Frontier Airlines
06:25MDW
16:09MCO
1 StopUSD 134VIEW DEAL
15 Sept
Frontier Airlines
06:25MDW
16:09MCO
1 StopUSD 152VIEW DEAL
16 Sept
Southwest Airlines
18:20MDW
21:05MCO
DirectUSD 123VIEW DEAL
16 Sept
Frontier Airlines
06:25MDW
16:09MCO
1 StopUSD 152VIEW DEAL
17 Sept
Southwest Airlines
09:20MDW
16:50MCO
1 StopUSD 132VIEW DEAL
17 Sept
Frontier Airlines
12:54MDW
00:45MCO
1 StopUSD 156VIEW DEAL
19 Sept
Frontier Airlines
13:06MDW
00:45MCO
1 StopUSD 136VIEW DEAL

Chicago to Orlando monthly flight fare trend

Sep
from USD 123
Oct
from USD 88
Nov
from USD 94
Dec
from USD 94
Jan
from USD 193
Feb
from USD 167

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

Flights from Chicago

Flights from Chicago to AtlantaFlights from Chicago to AustinFlights from Chicago to BostonFlights from Chicago to CharlotteFlights from Chicago to DenverFlights from Chicago to DallasFlights from Chicago to DetroitFlights from Chicago to NewarkFlights from Chicago to Fort LauderdaleFlights from Chicago to Honolulu