Chicago to Orlando

MDWMCO

Fly from Chicago to Orlando starting at USD 131 with Southwest Airlines.Best fare available on Oct 14, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Orlando cheapest flights this week

9 Oct
Frontier Airlines
06:40MDW
15:40MCO
1 StopUSD 138VIEW DEAL
9 Oct
Southwest Airlines
20:40MDW
23:15MCO
DirectUSD 215VIEW DEAL
9 Oct
Southwest Airlines
18:40MDW
21:15MCO
DirectUSD 179VIEW DEAL
10 Oct
Frontier Airlines
15:30MDW
00:37MCO
1 StopUSD 145VIEW DEAL
11 Oct
Southwest Airlines
19:00MDW
21:40MCO
DirectUSD 205VIEW DEAL
12 Oct
Southwest Airlines
07:45MDW
16:40MCO
1 StopUSD 148VIEW DEAL
12 Oct
Frontier Airlines
06:15MDW
16:21MCO
1 StopUSD 159VIEW DEAL
12 Oct
Southwest Airlines
20:40MDW
23:15MCO
DirectUSD 230VIEW DEAL
12 Oct
Southwest Airlines
18:40MDW
21:15MCO
DirectUSD 237VIEW DEAL
14 Oct
Southwest Airlines
13:35MDW
18:50MCO
1 StopUSD 131VIEW DEAL

Chicago to Orlando monthly flight fare trend

Oct
from USD 70
Nov
from USD 94
Dec
from USD 65
Jan
from USD 193
Feb
from USD 167
Mar
from USD 95

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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