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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 , 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  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 , 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  right now, why wait?

Chesapeake Flight Information
Destination airport
Chesapeake
Destination airport IATA code
PHF

Last Minute Hotel Deals in Chesapeake

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,027 reviews)
"The customer service was outstanding; the parking was fantastic and I felt very safe."

Reviewed on Oct 17, 2025

Comfort Suites Chesapeake - Norfolk
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
Stay at this hotel in Chesapeake. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.8/10 (1,005 reviews)
"Clean rooms"

Reviewed on Oct 10, 2025

Red Roof Inn Chesapeake Conference Center
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 a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.6/10 (609 reviews)
"Good"

Reviewed on Oct 16, 2025

STUDIOS & SUITES 4 LESS 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! (1,011 reviews)
"Stayed overnight because my flight was canceled, and I must say this hotel was one of the best in terms of room space and comfort. I would highly recommend this hotel!"

Reviewed on Oct 10, 2025

Wingate by Wyndham Chesapeake
Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
2800 Shore Drive, Virginia Beach, VA
Stay at this 4-star business-friendly hotel in Virginia Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the restaurant and the ...
8.4/10 Very Good! (1,416 reviews)
"One of the best hotels I’ve stayed at, really good service, and beautiful views, pool area is a great spot to spend time throughout the day in the summer time."

Reviewed on Oct 15, 2025

Delta Hotels by Marriott Virginia Beach Waterfront Suites
Schooner Inn

Schooner Inn

2 out of 5
215 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 convenient ...
8.6/10 Excellent! (3,602 reviews)
"Clean, quiet, relaxing all of the above!"

Reviewed on Oct 16, 2025

Schooner Inn
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
Stay at this 3-star beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,174 reviews)
"The hotel was spacious and clean. Erin and Matt were amazing and truly exemplified excellent customer service. Would definitely stay here again."

Reviewed on Oct 16, 2025

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
Oceans 2700

Oceans 2700

2.5 out of 5
2700 Pacific Avenue, Virginia Beach, VA
Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,500 reviews)
"Centrally located!"

Reviewed on Oct 15, 2025

Oceans 2700
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
Stay at this 3-star 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! (646 reviews)
"Quick trip on our way to the beach. Very friendly staff. Would stay here again."

Reviewed on Aug 24, 2025

Hilton Garden Inn Chesapeake/Greenbrier
Hyatt Place Chesapeake

Hyatt Place Chesapeake

3 out of 5
709 Eden Way N, Chesapeake, VA
Stay at this 3-star 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! (1,009 reviews)
"Breakfast was great and staff was very kind"

Reviewed on Oct 18, 2025

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.