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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

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 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! (1,043 reviews)
"Shower was broken. Water pressure was only available when at l"

Reviewed on May 18, 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! (806 reviews)
"Parking lot well lite, felt safe ,friendly staff, very clean rooms with refrigerator, microwave, tv w/remote ,the cleaning lady was so friendly and awsome getting us fresh towels everyday . Great pricing ,place is close to everything we needed ."

Reviewed on May 18, 2026

STUDIOS & SUITES 4 LESS CHESAPEAKE
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 ...
9.6/10 Exceptional! (79 reviews)
"Super clean room! Loved the addition of the washer and dryer in each room."

Reviewed on May 18, 2026

YourSpace Hotels Chesapeake
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
1570 CROSSWAYS BLVD Chesapeake VA
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (462 reviews)
"Property was clean. Staff was nice. Centrally located. Lots of stores nearby. Plenty of places to eat nearby. Breakfast in the morning was good. Reasonably priced"

Reviewed on May 17, 2026

TRU by Hilton Chesapeake, VA
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! (1,002 reviews)
"Breakfast was good and filling. Parking was great, we felt safe and love the location."

Reviewed on May 17, 2026

Holiday Inn Express Chesapeake - Norfolk by IHG
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! (1,832 reviews)
"Enjoyed dancing at the Surf Club room. The only problem I h ad with the room was that it took so very long for the water in the bathroom to get hot."

Reviewed on May 18, 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! (2,302 reviews)
"Loved staying at this hotel! Beautiful beach-front views from our room - even watched the sunrise a couple days! Great little patio with two chairs and a table with sliding glass door off the room got used a lot. Wonderful free breakfast (the potatoes were so good!) had pretty much anything you could ..."

Reviewed on May 18, 2026

Hyatt Place Virginia Beach / Oceanfront
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

3 out of 5
1801 Atlantic Ave Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (2,574 reviews)
"The room was fine, had a nice ocean view. The parking garage is horrible to navigate and our door to our room had a giant gap in the frame that wasn’t addressed."

Reviewed on May 18, 2026

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
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! (664 reviews)
"Check in and out process was easy, room was spacious and smelled great. Would definitely recommend this place to anyone coming to Virgina Beach"

Reviewed on May 3, 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! (1,004 reviews)
"Room was clean and spacious. Beds are very soft, but not super comfortable."

Reviewed on May 16, 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.