Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at USD 105 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

20 Jun
Frontier Airlines
17:15MCO
23:11MDW
1 Stop$158VIEW DEAL
26 Jun
Frontier Airlines
15:10MCO
23:11MDW
1 Stop$157VIEW DEAL
28 Jun
Frontier Airlines
05:40MCO
16:15MDW
1 Stop$165VIEW DEAL
29 Jun
Frontier Airlines
17:10MCO
23:11MDW
1 Stop$132VIEW DEAL
14 Jul
Southwest Airlines
18:10MCO
21:10MDW
Direct$105VIEW DEAL
28 Aug
Frontier Airlines
17:10MCO
23:11MDW
1 Stop$117VIEW DEAL

Orlando to Chicago monthly flight fare trend

Jun
from USD 98
Jul
from USD 105
Aug
from USD 117
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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