Chesapeake, Virginia, is a charming city that blends natural beauty with rich history and a thriving community. Located in the Hampton Roads region, it is known for its scenic landscapes, including the expansive Great Dismal Swamp National Wildlife Refuge and miles of peaceful waterways perfect for boating and fishing. The city boasts a mix of rural tranquility and suburban convenience, with historic sites, outdoor recreation, and family-friendly attractions. Whether exploring its lush parks, enjoying local festivals, or learning about its role in early American history, Chesapeake offers a welcoming atmosphere for residents and visitors alike.
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 Chesapeake, Virginia 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.
Atlanta, Georgia (ATL) - 1 Hour 50 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?
Delta from ORF - See flight deals
Frontier from ORF - See flight deals
How much will it cost to get there?
Airfare: $200+
Where can you stay?
Who will pick you up?
Pro Tip:
Walk some of the BeltLine and stop at stores, bars, and restaurants.
Boston, Massachusetts (BOS) - 1 Hour 45 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 ORF - See flight deals
JetBlue from ORF - See flight deals
Southwest from ORF - See flight deals
How much will it cost to get there?
Airfare: $300+
Where can you stay?
Who will pick you up?
New York, New York (JFK, LGA, EWR, ISP, HPN) - 1 Hour 25 Minute Flight
Why go?
It might not be the same city it was before, but it'll always make for a great weekend getaway.
What to do?
Click here to view The BEST Things to Do in New York
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?
AA from ORF - See flight deals
Delta from ORF - See flight deals
United from ORF - See flight deals
How much will it cost to get there?
Airfare: $300+
Where can you stay?
Who will pick you up?
Miami, Florida (MIA, FLL) - 2 Hour 25 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?
AA from ORF - See flight deals
Spirit Airways from ORF - See flight deals
Southwest from ORF - See flight deals
How much will it cost to get there?
Airfare: $100+
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 10 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?
AA from ORF - See flight deals
Southwest from ORF - See flight deals
United from ORF - See flight deals
How much will it cost to get there?
Airfare: $250+
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.
Washington, DC (IAD, DCA, BWI) - 1 Hour 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 ORF - See flight deals
AA from ORF - See flight deals
Allegiant from ORF - See flight deals
United from ORF - See flight deals
How much will it cost to get there?
Airfare: $200+
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.
Orlando, Florida (MCO) - 2 Hour 10 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?
Allegiant from ORF - See flight deals
Spirit Airways from ORF - See flight deals
Frontier from ORF - See flight deals
Southwest from ORF - See flight deals
How much will it cost to get there?
Airfare: $120+
Where can you stay?
Who will pick you up?
Philadelphia, Pennsylvania (PHL) - 1 Hour 8 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?
AA from ORF - See flight deals
Spirit Airlines from ORF - See flight deals
Southwest from ORF - See flight deals
Frontier Airlines from ORF - See flight deals
How much will it cost to get there?
Airfare: $350+
Where can you stay?
Who will pick you up?
Nashville, Tennessee (BNA) - 2 Hour 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?
United from ORF - See flight deals
Southwest from ORF - See flight deals
Frontier from ORF - See flight deals
How much will it cost to get there?
Airfare: $300+
Where can you stay?
Who will pick you up?
Pro Tip:
Stay in the Gulch or near printer's alley.
Comments