FFL Helper / Weekends / MDW (Chicago)

Weekend from MDW

Weekend hops from Chicago Midway (MDW)

Explore weekend getaways departing from MDW (Chicago) with flight times under six hours.

St Louis STL

$72

Dec 21, 9:25pm · 1h 20m · 0 stops

MDW → STL · Southwest Airlines

Tickets

Minneapolis MSP

$72

Dec 14, 11:40am · 1h 30m · 0 stops

MDW → MSP · Southwest Airlines

Tickets

Denver DEN

$78

Nov 12, 5:55am · 2h 50m · 0 stops

MDW → DEN · Southwest Airlines

Tickets

Philadelphia PHL

$86

Nov 12, 3:50pm · 1h 55m · 0 stops

MDW → PHL · Southwest Airlines

Tickets

Atlanta ATL

$90

Nov 24, 1:16pm · 2h 8m · 0 stops

MDW → ATL · Frontier Airlines

Tickets

Detroit DTT

$103

Nov 24, 7:45am · 1h 10m · 0 stops

MDW → DTW · Southwest Airlines

Tickets

Ontario ONT

$103

Dec 09, 3:55pm · 4h 20m · 0 stops

MDW → ONT · Southwest Airlines

Tickets

Punta Gorda PGD

$138

Nov 05, 10:12am · 2h 48m · 0 stops

MDW → PGD · Allegiant Air

Tickets

Cleveland CLE

$141

Oct 23, 5:00am · 6h · 1 stop

MDW → CLE · Southwest Airlines

Tickets

Buffalo BUF

$141

Oct 28, 6:16am · 5h 59m · 1 stop

MDW → BUF · Frontier Airlines

Tickets

Seattle SEA

$142

Nov 13, 10:00pm · 4h 45m · 0 stops

MDW → SEA · Southwest Airlines

Tickets

Guadalajara GDL

$145

Dec 25, 6:17pm · 4h 20m · 0 stops

MDW → GDL · Volaris

Tickets

Ad. Ticket links are affiliate ads. We may earn a commission if you book. Advertising disclosure

This page lists cheap one-way fares leaving MDW (Chicago), not arrivals. Scan the table for date, duration, and stops, then open a destination if you want a two-month price calendar.

Fares from MDW (Chicago) change as seats sell. Recheck the route before you buy, and if your metro has more than one airport, compare those boards as well.