Orlando to Chicago

MCOMDW

Fly from Orlando to Chicago starting at SAR 366 with Frontier Airlines.Best fare available on Aug 24, 2026.Limited seats. Better plans. Book before it's gone.

Orlando to Chicago cheapest flights this week

5 Aug
Frontier Airlines
13:45MCO
23:03MDW
1 StopSAR 544VIEW DEAL
5 Aug
Southwest Airlines
07:40MCO
10:25MDW
DirectSAR 618VIEW DEAL
6 Aug
Frontier Airlines
15:18MCO
23:03MDW
1 StopSAR 622VIEW DEAL
6 Aug
Frontier Airlines
17:24MCO
23:03MDW
1 StopSAR 703VIEW DEAL
15 Aug
Frontier Airlines
07:45MCO
23:03MDW
1 StopSAR 463VIEW DEAL
19 Aug
Southwest Airlines
19:15MCO
22:00MDW
DirectSAR 477VIEW DEAL
19 Aug
Frontier Airlines
17:23MCO
23:47MDW
1 StopSAR 655VIEW DEAL
20 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectSAR 422VIEW DEAL
24 Aug
Southwest Airlines
06:55MCO
09:45MDW
DirectSAR 414VIEW DEAL
24 Aug
Frontier Airlines
10:03MCO
23:47MDW
1 StopSAR 366VIEW DEAL

Orlando to Chicago monthly flight fare trend

Aug
from SAR 363
Sep
from SAR 422
Oct
from SAR 377
Nov
from SAR 477
Dec
from SAR 426
Jan
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

Flights from Orlando

Flights from Orlando to AtlantaFlights from Orlando to AustinFlights from Orlando to BostonFlights from Orlando to CharlotteFlights from Orlando to DenverFlights from Orlando to DallasFlights from Orlando to DetroitFlights from Orlando to NewarkFlights from Orlando to Fort LauderdaleFlights from Orlando to Honolulu