Chicago to Orlando

MDWMCO

Fly from Chicago to Orlando starting at USD 102 with Southwest Airlines.Best fare available on Aug 22, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Orlando cheapest flights this week

8 Jul
Frontier Airlines
12:11MDW
17:33MCO
1 StopUSD 195VIEW DEAL
9 Jul
Frontier Airlines
12:11MDW
18:50MCO
1 StopUSD 186VIEW DEAL
10 Jul
Frontier Airlines
06:05MDW
13:23MCO
1 StopUSD 151VIEW DEAL
12 Jul
Frontier Airlines
06:05MDW
13:23MCO
1 StopUSD 182VIEW DEAL
17 Jul
Frontier Airlines
12:11MDW
21:15MCO
1 StopUSD 158VIEW DEAL
18 Jul
Frontier Airlines
12:11MDW
18:50MCO
1 StopUSD 155VIEW DEAL
16 Aug
Frontier Airlines
06:05MDW
18:57MCO
1 StopUSD 130VIEW DEAL
17 Aug
Southwest Airlines
19:50MDW
22:20MCO
DirectUSD 115VIEW DEAL
22 Aug
Southwest Airlines
15:40MDW
18:15MCO
DirectUSD 102VIEW DEAL
24 Aug
Southwest Airlines
14:55MDW
17:30MCO
DirectUSD 115VIEW DEAL

Chicago to Orlando monthly flight fare trend

Jul
from USD 151
Aug
from USD 102
Sep
from USD 104
Oct
from USD 102
Nov
No flights
Dec
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

Flights from Chicago

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