MDW (Chicago) to MCO (Orlando) in September 2026

Dated one-way fares from MDW (Chicago) to MCO (Orlando) in September 2026. Use the calendar to see which days are cheaper.

Lowest this month $132

Highest this month $168

Sample fare $129

Airports MDW–MCO

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September 2026 price calendar

From $132 · up to $168

Mon

Tue

Wed

Thu

Fri

Sat

Sun

2 $168 3 $150 4 $150 5 $150 6 $150 7 $150 8 $150 9 $150 10 $150 11 $150 12 $150 13 $150 14 $150 15 $150 16 $150 17 $132

Orlando ORL

$129

Oct 31, 6:25am · 4h · 1 stop

MDW → MCO · Southwest Airlines

This page is only September 2026 on the MDW (Chicago) to MCO (Orlando) route. Open the full route if you want the next months side by side.

Prices move as seats sell. Confirm the live itinerary before you book MDW (Chicago) to MCO (Orlando) in September 2026.