FFL Helper / Weekends / MDW (Chicago)

Weekend from MDW

Weekend getaways from MDW (Chicago)

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

Cleveland CLE

$61

Sep 21, 4:25pm · 1h 15m · 0 stops

MDW → CLE · Southwest Airlines

Tickets

Pittsburgh PIT

$72

Oct 12, 7:45pm · 1h 20m · 0 stops

MDW → PIT · Southwest Airlines

Tickets

Atlanta ATL

$81

Sep 06, 6:05am · 2h 17m · 0 stops

MDW → ATL · Frontier Airlines

Tickets

Dallas DFW

$82

Sep 16, 6:25am · 5h 47m · 1 stop

MDW → DFW · Frontier Airlines

Tickets

Toronto YTO

$85

Sep 25, 3:20pm · 1h 40m · 0 stops

MDW → YTZ · Porter Airlines Canada

Tickets

Los Angeles LAX

$100

Oct 02, 3:55pm · 4h 30m · 0 stops

MDW → LAX · Southwest Airlines

Tickets

Houston HOU

$102

Oct 05, 9:30pm · 2h 35m · 0 stops

MDW → HOU · Southwest Airlines

Tickets

Louisville SDF

$112

Nov 11, 6:15pm · 1h 15m · 0 stops

MDW → SDF · Southwest Airlines

Tickets

Boston BOS

$115

Sep 12, 9:05am · 2h 20m · 0 stops

MDW → BOS · Southwest Airlines

Tickets

Morelia MLM

$127

Oct 01, 2:32pm · 3h 59m · 0 stops

MDW → MLM · Volaris

Tickets

Raleigh RDU

$130

Sep 11, 6:46pm · 4h 43m · 1 stop

MDW → RDU · Frontier Airlines

Tickets

Buffalo BUF

$131

Sep 07, 8:05am · 1h 40m · 0 stops

MDW → BUF · Southwest Airlines

Tickets

San Jose SJC

$135

Sep 17, 8:50pm · 4h 35m · 0 stops

MDW → SJC · Southwest Airlines

Tickets

Oakland OAK

$135

Oct 20, 8:35pm · 4h 40m · 0 stops

MDW → OAK · Southwest Airlines

Tickets

Kansas City MKC

$136

Sep 28, 6:20am · 1h 25m · 0 stops

MDW → MCI · Southwest Airlines

Tickets

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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.