Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at USD 102 with Frontier Airlines.Best fare available on Aug 25, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

1 Jul
Southwest Airlines
20:50MCO
07:40MDW
1 StopUSD 244VIEW DEAL
3 Jul
Southwest Airlines
06:50MCO
11:00MDW
1 StopUSD 161VIEW DEAL
4 Jul
Southwest Airlines
13:25MCO
16:10MDW
DirectUSD 194VIEW DEAL
6 Jul
Frontier Airlines
05:40MCO
18:22MDW
1 StopUSD 151VIEW DEAL
11 Jul
Frontier Airlines
17:24MCO
23:03MDW
1 StopUSD 182VIEW DEAL
12 Jul
Frontier Airlines
15:18MCO
23:03MDW
1 StopUSD 151VIEW DEAL
14 Jul
Southwest Airlines
18:10MCO
21:10MDW
DirectUSD 105VIEW DEAL
14 Jul
Frontier Airlines
05:20MCO
12:07MDW
1 StopUSD 134VIEW DEAL
24 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectUSD 112VIEW DEAL
25 Aug
Frontier Airlines
17:23MCO
23:47MDW
1 StopUSD 102VIEW DEAL

Orlando to Chicago monthly flight fare trend

Jul
from USD 105
Aug
from USD 102
Sep
No flights
Oct
from USD 102
Nov
No flights
Dec
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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