Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at SAR 389 with Southwest Airlines.Best fare available on Jul 14, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

26 Jun
Frontier Airlines
15:10MCO
23:11MDW
1 StopSAR 581VIEW DEAL
28 Jun
Frontier Airlines
05:40MCO
16:15MDW
1 StopSAR 611VIEW DEAL
29 Jun
Frontier Airlines
17:10MCO
23:11MDW
1 StopSAR 488VIEW DEAL
14 Jul
Southwest Airlines
18:10MCO
21:10MDW
DirectSAR 389VIEW DEAL
28 Aug
Frontier Airlines
17:10MCO
23:11MDW
1 StopSAR 433VIEW DEAL

Orlando to Chicago monthly flight fare trend

Jun
from SAR 363
Jul
from SAR 389
Aug
from SAR 433
Sep
No flights
Oct
No flights
Nov
No flights

Airport Details

Origin

Orlando

Orlando International Airport (MCO)

Orlando, MCO
Zone

New York

Elev

96 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

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