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Chesapeake

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Chesapeake Flights as Low as $56

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

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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 PHF 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 June, 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 15 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 Norfolk Intl. 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 $56, 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 $56 right now, why wait?

Chesapeake Flight Information
Destination airport
Norfolk Intl.
Destination airport IATA code
ORF
Roundtrip price
$56

Last Minute Hotel Deals in Chesapeake

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,009 reviews)
It's ok for a night's rest. Quiet neighbor. TV remote did not work. Bath tub is old and has mold. It's acceptable for the price.

Reviewed on Apr 24, 2026

Wingate by Wyndham Chesapeake
STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy Chesapeake VA
Stay at this hotel in Chesapeake. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (781 reviews)
Good services rooms are clean staff are nice and welcoming. Best stay good prices

Reviewed on Apr 25, 2026

STUDIOS & SUITES 4 LESS CHESAPEAKE
Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive Chesapeake VA
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,001 reviews)
The property has not been well maintained. My room had water damage on the ceiling and a wall and the blinds didn’t work. The second room wreaked of cigarette smoke. Hated it. Not at all like 21st street property.

Reviewed on Apr 23, 2026

Holiday Inn Express Chesapeake - Norfolk by IHG
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Chesapeake Square ...
9.4/10 Exceptional! (46 reviews)
Everything was great!

Reviewed on Apr 24, 2026

YourSpace Hotels Chesapeake
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff ...
7.8/10 Good! (1,794 reviews)
Beautiful ocean view and staff were very accommodating.

Reviewed on Apr 25, 2026

Wyndham Virginia Beach Oceanfront
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (2,232 reviews)
Great breakfast

Reviewed on Apr 25, 2026

Hyatt Place Virginia Beach / Oceanfront
Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

4 out of 5
3001 Atlantic Ave Virginia Beach VA
Book a stay at this beach resort in Virginia Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,156 reviews)
Pool was closed for repairs. Not that big of a deal. Front counter was a bunch of getto ass blacks stealing hotel blind. Valet was nice though.

Reviewed on Apr 22, 2026

Hilton Virginia Beach Oceanfront
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,278 reviews)
Our trip was for a week. Probably would do something different for a longer stay in the future. But if you plan a quick weekend trip it’s okay. Pool was closed. And the hotel does not offer much of anything extra. You have to park a couple blocks away. And if there is an event you can’t pull your ...

Reviewed on Apr 25, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
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.

Top Hotels With Free Airport Shuttle

Hilton Garden Inn Chesapeake/Greenbrier

Hilton Garden Inn Chesapeake/Greenbrier

3 out of 5
1565 Crossways Blvd Chesapeake VA
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (661 reviews)
The only thing that was wrong was when I checked in the lady that checked us in was not very pleasant and our room wasn’t ready when we got there check in was at 3 and we got there at 340 and the room was not ready according to the lady at the desk. We drive 12 hours and I was very tired and just ...

Reviewed on Mar 24, 2026

Hilton Garden Inn Chesapeake/Greenbrier
Hyatt Place Chesapeake

Hyatt Place Chesapeake

3 out of 5
709 Eden Way N Chesapeake VA
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
A great hotel to stay at

Reviewed on Apr 21, 2026

Hyatt Place 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.