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  • Writer's pictureJordan Hinsch

20 Best Weekend Getaways from Orlando (within a 4-hour flight)

Updated: Feb 6



Orlando is the largest travel and tourism destination in the country. Theme parks are the primary driver of tourism along with the space coast and the 2nd largest largest convention center in the US. If you've ever traveled TO Orlando, you may notice the airfare is quite inexpensive (to attract tourists). Well, if you live in Orlando, you're in the right spot to take advantage of very low airfare. If you are a local and looking for a change of pace, read on!


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 Orlando 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.






Miami, Florida (MIA, FLL) - 1 Hour Flight


Why go?

  • Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.

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?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?

Pro Tip:

  • Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.






New York, New York (JFK, LGA, EWR, ISP, HPN) - Just Under a 3 Hour Flight


Why go?

  • It might not be the same city it was before, but it'll always make for a great weekend getaway.

When to go?

  • Summer for the best weather, but you’ll pay peak rates for solid hotels.

  • Winter for Christmas festivities!

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?





Toronto, Ontario (YYZ, YTZ) - 3 Hour Flight


Why go?

  • Food, people, cleanliness, Hockey Hall of Fame.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $300+

Where can you stay?





Philadelphia, Pennsylvania (PHL) - 2.5 Hour Flight


Why go?

  • History, sports, cheesesteaks

When to go?

  • Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?





Washington, DC (IAD, DCA, BWI) - Just Over a 2 Hour Flight


Why go?

  • Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.

When to go?

  • Year-round (spring season for cherry blossoms)

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?

Pro Tip:

  • For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.




Chicago, Illinois (ORD, MDW) - 3 Hour Flight


Why go?

  • Food, bars, sports, rivers!

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?

Pro Tip:

  • For bourbon enthusiasts, visit Untitled Supper Club on W Kinzie for an incredible speakeasy experience.




Kansas City, Missouri (MCI) - 3 Hour Flight


Why go?

  • BBQ! BBQ! BBQ!

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $250+

Where can you stay?

Pro Tip:

  • Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.






Nashville, Tennessee (BNA) - 2 Hour Flight


Why go?

  • Music (not just country), endless bars, brewpubs, hot chicken.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?

Pro Tip:

  • Stay in the Gulch or near printer's alley.




New Orleans, Louisiana (MSY) - Just Under a 2 Hour Flight


Why go?

  • Jazz music, other music, culture, architecture, partying, passionate football fans.

When to go?

  • Spring, Summer, Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $75+

Where can you stay?

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.





Atlanta, Georgia (ATL) - 1.5 Hour Flight


Why go?

  • Brew pubs, art, nightlife, Mexican food.

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?

Pro Tip:

  • Walk some of the BeltLine and stop at stores, bars, and restaurants.





Raleigh, North Carolina (RDU) - 2 Hour Flight


Why go?

  • Outdoors activities, restaurants, college sports, booming tech sector.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?






Austin, Texas (AUS) - Just Under a 3 Hour Flight


Why go?

  • Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?






Cancun, Mexico (CUN) - Just Over a 2 Hour Flight


Why go?

  • Your money goes a long way: all-inclusive hotels, nightlife, and activities.

When to go?

  • December to April for the best weather.

  • Avoid March Spring Break travel if you want to be at peace.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $150+

Where can you stay?






Boston, Massachusetts (BOS) - 3 Hour Flight



Why go?

  • History and cool summertime temps!

When to go?

  • Summer for the best weather, but peak rates for solid hotels.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $75+

Where can you stay?





Denver, Colorado (DEN) - Just Over a 4 Hour Flight


Why go?

  • Mountains, beer, National Parks, hiking, clean city, nice people.

When to go?

  • Year-round. Ski in the winter. Hike in the summer.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?





Nassau, Bahamas (NAS) - 1.5 Hour Flight


Why go?

  • Turquoise waters, friendly people, and close proximity to Florida make the Bahamas a popular destination.

When to go?

  • December - July to avoid hurricanes and tropical storms.

  • May - August to avoid crowds and surcharges.

  • November - February to avoid the summer heat.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $400+

Where can you stay?

Pro Tip:

  • Rent a car! Be prepared to drive on the left side of the road.






San Juan, Puerto Rico (SJU) - Just Under a 3 Hour Flight


Why go?

  • Surfing, culture, and hiking. Oh and you don't need a passport to travel.

When to go?

  • December - July to avoid hurricanes and tropical storms.

  • April - June to avoid the busy winter and the upcoming rainy season.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $150+

Where can you stay?




Charleston, South Carolina (CHS) - 1.5 Hour Flight


Why go?

  • History, culture, family-friendly attractions, and water sports.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?




Asheville, North Carolina (AVL) - 1.5 Hour Flight


Why go?

  • Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?





Montreal, Quebec (YUL) - 3 Hour Flight


Why go?

  • More restaurants per capita than any other North American city.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $350+

Where can you stay?





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Hey! I'm Jordan, a native New Yorker who is addicted to adventure travel, photography, content creation, investing, and fitness. Read on, enjoy, and Never Run Out of First Times!

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