Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at USD 109 with Frontier Airlines.Best fare available on Sep 9, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

5 Sept
Frontier Airlines
17:23MCO
23:47MDW
1 StopUSD 172VIEW DEAL
6 Sept
Southwest Airlines
07:25MCO
10:10MDW
DirectUSD 157VIEW DEAL
6 Sept
Frontier Airlines
17:23MCO
23:47MDW
1 StopUSD 159VIEW DEAL
6 Sept
Frontier Airlines
08:35MCO
21:31MDW
1 StopUSD 177VIEW DEAL
7 Sept
Frontier Airlines
17:23MCO
23:47MDW
1 StopUSD 204VIEW DEAL
7 Sept
Southwest Airlines
07:10MCO
12:25MDW
DirectUSD 245VIEW DEAL
8 Sept
Frontier Airlines
17:23MCO
18:51MDW
1 StopUSD 141VIEW DEAL
8 Sept
Southwest Airlines
19:15MCO
22:00MDW
DirectUSD 181VIEW DEAL
9 Sept
Frontier Airlines
07:14MCO
18:51MDW
1 StopUSD 119VIEW DEAL
9 Sept
Frontier Airlines
09:30MCO
18:51MDW
1 StopUSD 109VIEW DEAL

Orlando to Chicago monthly flight fare trend

Sep
from USD 99
Oct
from USD 102
Nov
from USD 120
Dec
from USD 99
Jan
No flights
Feb
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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