Find low fares on Southwest Airlines® flights from or within the Northeast
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Flying from the Northeast.
There are new adventures awaiting you outside of New England—and not just in other states in the Northeast. Travel further south down the Eastern Seaboard or trade the East Coast for the lapping waves of the Pacific Ocean. Consider having a Gulf State adventure or exploring the small towns and megalopolises of the Great Lakes. There’s plenty to choose from when you hop a Southwest flight winging away from Northeast origin cities. See where Southwest flies and start checking places off your bucket list.
Low Fares from the Northeast
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Boston (BOS)to
Chicago (Midway) (MDW)Depart: 02/11/2026
From
$42
One-way
Basic
Pittsburgh (PIT)to
Chicago (Midway) (MDW)Depart: 01/29/2026
From
$46
One-way
Basic
Hartford/Springfield (BDL)to
Chicago (Midway) (MDW)Depart: 02/10/2026
From
$47
One-way
Basic
Rochester (ROC)to
Orlando (MCO)Depart: 01/20/2026
From
$49
One-way
Basic
New York (LaGuardia) (LGA)to
Nashville (BNA)Depart: 02/18/2026
From
$50
One-way
Basic
New York (LaGuardia) (LGA)to
Orlando (MCO)Depart: 02/18/2026
From
$51
One-way
Basic
Rochester (ROC)to
Miami (MIA)Depart: 01/20/2026
From
$51
One-way
Basic
Rochester (ROC)to
Tampa (TPA)Depart: 01/27/2026
From
$51
One-way
Basic
New York (LaGuardia) (LGA)to
Chicago (Midway) (MDW)Depart: 02/24/2026
From
$52
One-way
Basic
Boston (BOS)to
Nashville (BNA)Depart: 01/28/2026
From
$52
One-way
Basic
Philadelphia (PHL)to
Chicago (Midway) (MDW)Depart: 01/08/2026
From
$53
One-way
Basic
Rochester (ROC)to
West Palm Beach (PBI)Depart: 01/13/2026
From
$53
One-way
Basic
*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.
Plan your trip from the Northeast
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Free inflight WiFi thanks to T-Mobile®.2
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12022–2023 Freddie Awards. 2Where available. Available only on WiFi-enabled designated aircraft. Free WiFi is only for Rapid Rewards® Members.