17 Best Weekend Getaways from Long Island, New York (within a 4-hour flight)
- Jordan Hinsch
- 3 days ago
- 8 min read
Long Island, New York, is a densely populated island in the southeastern part of the state, extending east of New York City. Known for its beautiful beaches, charming towns, and vibrant cultural scene, it spans four counties: Nassau, Suffolk, Queens, and Brooklyn. Popular attractions include the Hamptons, Montauk Point, and wineries along the North Fork. Long Island is also home to historical landmarks, scenic parks, and a thriving suburban community with close ties to NYC.
If you're a local and looking to escape for a weekend, keep reading. With a vast array of short domestic destinations, there are also some international destinations within reach. Here are some weekend getaway ideas for locals in the Long Island, New York, area within a non-stop 4-hour flight. More importantly, these trips are all possible without having to request PTO (for you M-F 9-5'ers), it just depends on what you want to do at your destination.
Boston, Massachusetts (BOS) - 54 Minute Flight
Why go?
History and cool summertime temps!
What to do?
Click here to view The BEST Things to Do in Boston
When to go?
Summer for the best weather, but peak rates for solid hotels.
Who can fly you there?
Delta from JFK - See flight deals
JetBlue from LGA - See flight deals
American from JFK - See flight deals
How much will it cost to get there?
Airfare: $182+
Where can you stay?
Who will pick you up?
Miami, Florida (MIA, FLL) - 3 Hour 15 Minute Flight
Why go?
Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.
What to do?
Click here to view The BEST Things to Do in Miami
When to go?
Any time of the year, but best is October - February for perfect weather. Avoid the spring break crowd in late Feb/early March the best you can.
Who can fly you there?
Frontier from LGA - See flight deals
Spirit from LGA - See flight deals
Frontier from ISP - See flight deals
How much will it cost to get there?
Airfare: $57+
Where can you stay?
Who will pick you up?
Pro Tip:
Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.
Chicago, Illinois (ORD, MDW) - 2 Hour 35 Minute Flight
Why go?
Food, bars, sports, rivers!
What to do?
Click here to view The BEST Things to Do in Chicago
When to go?
Summer
Who can fly you there?
Spirit from LGA - See flight deals
Southwest from LGA - See flight deals
United from LGA - See flight deals
How much will it cost to get there?
Airfare: $85+
Where can you stay?
Who will pick you up?
Pro Tip:
For bourbon enthusiasts, visit Untitled Supper Club on W Kinzie for an incredible speakeasy experience.
Orlando, Florida (MCO) - 3 Hour 1 Minute Flight
Why go?
Theme parks. Disney & Universal. Bring bug spray and an umbrella if you go during the summer. It's not my favorite city, but there's a reason why it's the #1 tourism city year after year in the US.
What to do?
Click here to view The BEST Things to Do in Orlando
When to go?
Year-Round
Who can fly you there?
Spirit LGA - See flight deals
Frontier from ISP - See flight deals
How much will it cost to get there?
Airfare: $47+
Where can you stay?
Who will pick you up?York
Atlanta, Georgia (ATL) - 2 Hour 41 Minute Flight
Why go?
Brew pubs, art, nightlife, Mexican food.
What to do?
Click here to view The BEST Things to Do in Atlanta
When to go?
Year-round
Who can fly you there?
Frontier from JFK - See flight deals
Frontier from LGA - See flight deals
Spirit from LGA - See flight deals
How much will it cost to get there?
Airfare: $43+
Where can you stay?
Who will pick you up?
Pro Tip:
Walk some of the BeltLine and stop at stores, bars, and restaurants.
New Orleans, Louisiana (MSY) - 3 Hour 29 Minute Flight
Why go?
Jazz music, other music, culture, architecture, partying, passionate football fans.
What to do?
Click here to view The BEST Things to Do in New Orleans
When to go?
Spring, Summer, Fall
Who can fly you there?
Spirit from LGA - See flight deals
American from LGA - See flight deals
Southwest from LGA - See flight deals
How much will it cost to get there?
Airfare: $86+
Where can you stay?
Who will pick you up?
Pro Tip:
Check out Bourbon Street for a little bit, but don't get sucked in. It's absolutely disgusting. Chartres Street is better for those looking to maintain their cleanliness.
Washington, DC (IAD, DCA, BWI) - 1 Hour 20 Minute Flight
Why go?
Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.
What to do?
Click here to view The BEST Things to Do in Washington DC
When to go?
Year-round (spring season for cherry blossoms)
Who can fly you there?
Southwest from ISP - See flight deals
American from LGA - See flight deals
United from LGA - See flight deals
How much will it cost to get there?
Airfare: $113+
Where can you stay?
Who will pick you up?
Pro Tip:
For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.
Toronto, Ontario (YYZ, YTZ) - 1 Hour 40 Minute Flight
Why go?
Food, people, cleanliness, Hockey Hall of Fame.
What to do?
Click here to view The BEST Things to Do in Toronto
When to go?
Summer
Who can fly you there?
Air Canada from LGA - See flight deals
American from LGA - See flight deals
Flair Airlines from JFK - See flight deals
How much will it cost to get there?
Airfare: $172+
Where can you stay?
Who will pick you up?
Nashville, Tennessee (BNA) - 2 Hour 38 Minute Flight
Why go?
Music (not just country), endless bars, brewpubs, hot chicken.
What to do?
Click here to view The BEST Things to Do in Nashville
When to go?
Spring, Summer and Fall
Who can fly you there?
JetBlue from JFK - See flight deals
American from LGA - See flight deals
Southwest from LGA - See flight deals
How much will it cost to get there?
Airfare: $125+
Where can you stay?
Who will pick you up?
Pro Tip:
Stay in the Gulch or near printer's alley.
Philadelphia, Pennsylvania (PHL) - 1 Hour 4 Minute Flight
Why go?
History, sports, cheesesteaks
What to do?
Click here to view The BEST Things to Do in Philadelphia
When to go?
Summer and Fall
Who can fly you there?
American from LGA - See flight deals
How much will it cost to get there?
Airfare: $303+
Where can you stay?
Who will pick you up?
Montreal, Quebec (YUL) - 1 Hour 24 Minute Flight
Why go?
More restaurants per capita than any other North American city.
What to do?
Click here to view The BEST Things to Do in Montreal
When to go?
Summer
Who can fly you there?
Air Canada from LGA - See flight deals
American from LGA - See flight deals
How much will it cost to get there?
Airfare: $250+
Where can you stay?
Who will pick you up?
Charleston, South Carolina (CHS) - 2 Hour 7 Minute Flight
Why go?
History, culture, family-friendly attractions, and water sports.
What to do?
Click here to view The BEST Things to Do in Charleston
When to go?
Spring, Summer and Fall
Who can fly you there?
Breeze from ISP - See flight deals
Spirit from LGA - See flight deals
Delta from LGA - See flight deals
How much will it cost to get there?
Airfare: $92+
Where can you stay?
Who will pick you up?
Asheville, North Carolina (AVL) - 2 Hour 6 Minute Flight
Why go?
Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!
What to do?
Click here to view The BEST Things to Do in Asheville
When to go?
Spring, Summer and Fall
Who can fly you there?
Delta from LGA - See flight deals
American from LGA - See flight deals
How much will it cost to get there?
Airfare: $192+
Where can you stay?
Who will pick you up?
Bermuda (BDA) - 2 Hour 5 Minute Flight
Why go?
Pink sand beaches and diving.
What to do?
Click here to view The BEST Things to Do in Bermuda
When to go?
Year-round (might want to avoid hurricane season)
Who can fly you there?
American from JFK - See flight deals
Delta from JFK - See flight deals
How much will it cost to get there?
Airfare: $361+
Where can you stay?
Who will pick you up?
Charlotte, North Carolina (CLT) – 2 Hour 4 Minute Flight
Why go?
Diverse Cultural Attractions, Thriving Food Scene, Outdoor Activities, Sports Hub, Historical Significance, Shopping, Festivals and Events.
What to do?
Click here to view The BEST Things to Do in Charlotte
When to go?
The best times to visit Charlotte are March–May and September–November.
Who can fly you there?
Frontier from LGA - See flight deals
Spirit from LGA - See flight deals
How much will it cost to get there?
Airfare: $33+
Where can you stay?
Who will pick you up?
Kansas City, Missouri (MCI) - 3 Hour 21 Minute Flight
Why go?
BBQ! BBQ! BBQ!
What to do?
Click here to view The BEST Things to Do in Kansas City
When to go?
Year-round
Who can fly you there?
Delta from JFK - See flight deals
Delta from LGA - See flight deals
How much will it cost to get there?
Airfare: $289+
Where can you stay?
Who will pick you up?
Pro Tip:
Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.
Portland, Oregon (PDX) - 1 Hour 26 Minute Flight
Why go?
Surfing. Oregon coast is only 1 hour away. Mt. Hood is nearby as well.
What to do?
Click here to view The BEST Things to Do in Portland
When to go?
Year-Round
Who can fly you there?
JetBlue from JFK - See flight deals
Delta from JFK - See flight deals
How much will it cost to get there?
Airfare: $124+
Where can you stay?
Who will pick you up?
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