MDW (Chicago) to Cleveland in September 2026

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

Lowest this month $61

Highest this month $233

Sample fare $61

Airports MDW–CLE

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September 2026 price calendar

From $61 · up to $233

Mon

Tue

Wed

Thu

Fri

Sat

Sun

2 $132 3 $182 4 $182 5 $182 6 $182 7 $233 8 $147 9 $147 10 $147 11 $147 12 $147 13 $147 14 $147 15 $147 16 $147 17 $147 18 $147 19 $147 20 $147 21 $61 22 $61 23 $61 24 $63 25 $63 26 $64

Cleveland CLE

$61

Sep 21, 4:25pm · 1h 15m · 0 stops

MDW → CLE · Southwest Airlines

Cleveland CLE

$61

Sep 23, 8:35am · 1h 25m · 0 stops

MDW → CLE · Southwest Airlines

This page is only September 2026 on the MDW (Chicago) to Cleveland 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 Cleveland in September 2026.