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Chesapeake

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Chesapeake Flights as Low as $268

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Fri, Aug 22 - Mon, Aug 25
PNS
Pensacola Intl.
HTS
Tri-State
$268 Roundtrip, found 3 days ago
$268
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug 22 from Pensacola Intl. to Tri-State, returning Mon, Aug 25, priced at $268 found 3 days ago
American Airlines
Fri, Aug 22 - Mon, Aug 25
PNS
Pensacola Intl.
HTS
Tri-State
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 22 from Pensacola Intl. to Tri-State, returning Mon, Aug 25, priced at $273 found 1 day ago
American Airlines
Fri, Aug 15 - Mon, Aug 18
PNS
Pensacola Intl.
HTS
Tri-State
$297 Roundtrip, found 3 days ago
$297
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug 15 from Pensacola Intl. to Tri-State, returning Mon, Aug 18, priced at $297 found 3 days ago
American Airlines
Wed, Aug 20 - Tue, Aug 26
PNS
Pensacola Intl.
HTS
Tri-State
$333 Roundtrip, found 3 days ago
$333
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Aug 20 from Pensacola Intl. to Tri-State, returning Tue, Aug 26, priced at $333 found 3 days ago
American Airlines
Tue, Aug 12 - Sat, Aug 16
PNS
Pensacola Intl.
HTS
Tri-State
$338 Roundtrip, found 2 hours ago
$338
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Aug 12 from Pensacola Intl. to Tri-State, returning Sat, Aug 16, priced at $338 found 2 hours ago
American Airlines
Fri, Aug 22 - Mon, Aug 25
PNS
Pensacola Intl.
HTS
Tri-State
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 22 from Pensacola Intl. to Tri-State, returning Mon, Aug 25, priced at $344 found 1 day ago
American Airlines
Fri, Aug 8 - Sun, Aug 10
PNS
Pensacola Intl.
HTS
Tri-State
$352 Roundtrip, found 2 days ago
$352
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Aug 8 from Pensacola Intl. to Tri-State, returning Sun, Aug 10, priced at $352 found 2 days ago
American Airlines
Tue, Aug 12 - Sat, Aug 16
PNS
Pensacola Intl.
HTS
Tri-State
$374 Roundtrip, found 2 hours ago
$374
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Aug 12 from Pensacola Intl. to Tri-State, returning Sat, Aug 16, priced at $374 found 2 hours ago
American Airlines
Thu, Aug 14 - Sun, Aug 17
PNS
Pensacola Intl.
HTS
Tri-State
$388 Roundtrip, found 2 hours ago
$388
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Aug 14 from Pensacola Intl. to Tri-State, returning Sun, Aug 17, priced at $388 found 2 hours ago
American Airlines
Fri, Aug 15 - Sun, Aug 17
PNS
Pensacola Intl.
HTS
Tri-State
$396 Roundtrip, found 2 hours ago
$396
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Aug 15 from Pensacola Intl. to Tri-State, returning Sun, Aug 17, priced at $396 found 2 hours ago
American Airlines
Mon, Aug 11 - Sun, Aug 17
PNS
Pensacola Intl.
HTS
Tri-State
$409 Roundtrip, found 2 hours ago
$409
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, Aug 11 from Pensacola Intl. to Tri-State, returning Sun, Aug 17, priced at $409 found 2 hours ago
American Airlines
Wed, Aug 20 - Sun, Aug 24
PNS
Pensacola Intl.
HTS
Tri-State
$419 Roundtrip, found 3 days ago
$419
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Aug 20 from Pensacola Intl. to Tri-State, returning Sun, Aug 24, priced at $419 found 3 days ago
American Airlines
Sat, Aug 9 - Wed, Aug 13
PNS
Pensacola Intl.
HTS
Tri-State
$424 Roundtrip, found 2 hours ago
$424
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Aug 9 from Pensacola Intl. to Tri-State, returning Wed, Aug 13, priced at $424 found 2 hours ago
American Airlines
Tue, Aug 19 - Sun, Aug 24
PNS
Pensacola Intl.
HTS
Tri-State
$426 Roundtrip, found 3 days ago
$426
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 19 from Pensacola Intl. to Tri-State, returning Sun, Aug 24, priced at $426 found 3 days ago
American Airlines
Fri, Aug 22 - Mon, Aug 25
PNS
Pensacola Intl.
HTS
Tri-State
$441 Roundtrip, found 3 days ago
$441
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug 22 from Pensacola Intl. to Tri-State, returning Mon, Aug 25, priced at $441 found 3 days ago
American Airlines
Tue, Aug 12 - Sat, Aug 16
PNS
Pensacola Intl.
HTS
Tri-State
$445 Roundtrip, found 2 hours ago
$445
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Aug 12 from Pensacola Intl. to Tri-State, returning Sat, Aug 16, priced at $445 found 2 hours ago

Cheap Flights to Chesapeake

Fall in love at first flight with your vacation to Chesapeake by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chesapeake on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chesapeake, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chesapeake

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chesapeake with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the HTS airport.

What is the cheapest month to fly to Chesapeake?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chesapeake are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chesapeake?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chesapeake.

What airport is best to fly into Chesapeake?

When you’re planning your trip to Chesapeake, convenience is the name of the game. Luckily, Chesapeake Tri-State Airport is nearby so you can deplane and get going on checking off everything on your Chesapeake must-do list.

How much are flights to Chesapeake?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chesapeake on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $268, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chesapeake?

The trick to saving a stack of cash on your flight to Chesapeake? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $268 right now, why wait?

Chesapeake Flight Information
Destination airport
Tri-State
Destination airport IATA code
HTS
Roundtrip price
$267

Last Minute Hotel Deals in Chesapeake

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

4 out of 5
1001 3rd Avenue, Huntington, WV
Stay at this 4-star business-friendly hotel in Huntington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,011 reviews)
"Convenience"

Reviewed on Aug 4, 2025

Get rates
DoubleTree by Hilton Huntington
Red Roof Inn Huntington

Red Roof Inn Huntington

2 out of 5
458 Braley Road, Huntington, WV
Stay at this hotel in Huntington. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (1,000 reviews)
"the room was accessible and to get in and out of"

Reviewed on Aug 4, 2025

Get rates
Red Roof Inn Huntington
Rodeway Inn

Rodeway Inn

2.5 out of 5
3441 US Route 60 E, Barboursville, WV
Book a stay at this business-friendly hotel in Barboursville. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
7.2/10 Good! (1,003 reviews)
"I LOVE this hotel and the STAFF IS SO AMAZING!! Kindest people you’ll ever meet."

Reviewed on Aug 6, 2025

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Rodeway Inn
Fairfield Inn & Suites by Marriott Huntington

Fairfield Inn & Suites by Marriott Huntington

2.5 out of 5
536 Kinetic Drive, Huntington, WV
Book a stay at this business-friendly hotel in Huntington. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,002 reviews)
"Very reliable hotel"

Reviewed on Aug 6, 2025

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Fairfield Inn & Suites by Marriott Huntington
Delta Hotels by Marriott Huntington Downtown

Delta Hotels by Marriott Huntington Downtown

3 out of 5
800 3rd Ave, Huntington, WV
Stay at this 3-star business-friendly hotel in Huntington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,003 reviews)
Our hotel
"This is our top choice hotel when we visit our son. The facility is great and the location makes it even more appealing. Normally, the staff is pleasant and easy to deal with. Something was off during this trip in the way they dealt with customers. It may have been a bad day because it was really ..."

Reviewed on Aug 1, 2025

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Delta Hotels by Marriott Huntington Downtown
Knights Inn Ashland

Knights Inn Ashland

1.5 out of 5
7216 Sr 60, Ashland, KY
Book a stay at this golf motel in Ashland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.8/10 (578 reviews)
"Nice"

Reviewed on Aug 3, 2025

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Knights Inn Ashland
Delta Hotels by Marriott Huntington Mall

Delta Hotels by Marriott Huntington Mall

3 out of 5
3551 US Route 60 East, Barboursville, WV
Stay at this 3-star business-friendly hotel in Barboursville. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful ...
8.8/10 Excellent! (1,000 reviews)
"The rms were clean, beds comfortable, the rm was cool. The staff was friendly and helpful."

Reviewed on Jul 28, 2025

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Delta Hotels by Marriott Huntington Mall
Ramada by Wyndham Catlettsburg/Ashland

Ramada by Wyndham Catlettsburg/Ashland

2.5 out of 5
6003 Centerline Drive, Catlettsburg, KY
Book a stay at this business-friendly hotel in Catlettsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (484 reviews)
"It was clean and the staff was friendly. The breakfast was lacking in options."

Reviewed on Jul 12, 2025

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Ramada by Wyndham Catlettsburg/Ashland
See all 158 properties in Chesapeake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.