Chicago to Orlando

MDWMCO

Fly from Chicago to Orlando starting at SAR 466 with Southwest Airlines.Best fare available on Oct 8, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Orlando cheapest flights this week

7 Oct
Frontier Airlines
06:25MDW
16:09MCO
1 StopSAR 648VIEW DEAL
7 Oct
Southwest Airlines
16:40MDW
19:15MCO
DirectSAR 718VIEW DEAL
8 Oct
Frontier Airlines
06:21MDW
11:10MCO
1 StopSAR 759VIEW DEAL
8 Oct
Southwest Airlines
18:40MDW
22:45MCO
1 StopSAR 466VIEW DEAL
9 Oct
Frontier Airlines
06:40MDW
15:40MCO
1 StopSAR 511VIEW DEAL
9 Oct
Southwest Airlines
20:40MDW
23:15MCO
DirectSAR 796VIEW DEAL
9 Oct
Southwest Airlines
18:40MDW
21:15MCO
DirectSAR 662VIEW DEAL
11 Oct
Southwest Airlines
19:00MDW
21:40MCO
DirectSAR 759VIEW DEAL
12 Oct
Southwest Airlines
07:45MDW
16:40MCO
1 StopSAR 548VIEW DEAL
12 Oct
Frontier Airlines
06:15MDW
16:21MCO
1 StopSAR 588VIEW DEAL

Chicago to Orlando monthly flight fare trend

Oct
from SAR 255
Nov
from SAR 348
Dec
from SAR 348
Jan
from SAR 714
Feb
from SAR 618
Mar
from SAR 470

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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