Chicago to Orlando

MDWMCO

Fly from Chicago to Orlando starting at USD 102 with Southwest Airlines.Best fare available on Oct 3, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Orlando cheapest flights this week

1 Oct
Frontier Airlines
12:03MDW
21:10MCO
1 StopUSD 123VIEW DEAL
1 Oct
Southwest Airlines
20:40MDW
23:10MCO
DirectUSD 206VIEW DEAL
3 Oct
Southwest Airlines
17:25MDW
20:00MCO
DirectUSD 102VIEW DEAL
3 Oct
Frontier Airlines
13:06MDW
00:45MCO
1 StopUSD 130VIEW DEAL
3 Oct
Southwest Airlines
19:00MDW
21:35MCO
DirectUSD 187VIEW DEAL
4 Oct
Frontier Airlines
18:46MDW
20:59MCO
1 StopUSD 148VIEW DEAL
4 Oct
Frontier Airlines
06:25MDW
07:09MCO
1 StopUSD 146VIEW DEAL
4 Oct
Southwest Airlines
05:10MDW
07:45MCO
DirectUSD 211VIEW DEAL
7 Oct
Frontier Airlines
06:25MDW
16:09MCO
1 StopUSD 134VIEW DEAL
7 Oct
Southwest Airlines
16:40MDW
19:15MCO
DirectUSD 194VIEW DEAL

Chicago to Orlando monthly flight fare trend

Sep
No flights
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

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