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Chesapeake

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Chesapeake Flights as Low as $184

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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 April, 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 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 $184, 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 $184 right now, why wait?

Chesapeake Flight Information
Destination airport
Norfolk Intl.
Destination airport IATA code
ORF
Roundtrip price
$183

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! (1,005 reviews)
The room seemed to be clean, but the towels had hair on them and the water pressure in the shower was very poor.

Reviewed on Mar 14, 2026

Wingate by Wyndham 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 ...
8.8/10 Excellent! (1,006 reviews)
Very polite , the room was clean , awesome job

Reviewed on Mar 14, 2026

Comfort Suites Chesapeake - Norfolk
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 ...
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! (1,001 reviews)
Don't miss out on the tasty complimentary breakfast to start your day!

Reviewed on Mar 8, 2026

Holiday Inn Express Chesapeake - Norfolk by IHG
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! (2,510 reviews)
Beds-comfortable. Room’s clean except the patio which had water dripping from above and soil from the lawn. This could be prevented by edging the cement edge. The breakfast was great. Typical hotel fare but the staff was amazingly friendly and on top of service. Rainy was super nice. The garage parking ...

Reviewed on Mar 14, 2026

Country Inn & Suites by Radisson, 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! (1,214 reviews)
We had a room on the 7th floor right on the boardwalk with a perfect view of the ocean. The ice and vending machines were directly across from our room and they have a nice club/restaurant on the ground floor that leads right out to the boardwalk. The only downside is the parking is around the block ...

Reviewed on Mar 13, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

3.5 out of 5
3401 Atlantic Ave Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, 2 indoor pools, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,255 reviews)
Our stay was amazing! Staff was extremely friendly and courteous. Our room was clean . We had a city view but that was perfectly fine as we were right on the beach. Lastly our only complaint was the size of the bed. We booked for a queen and the bed was definitely a full size bed. Other than that ...

Reviewed on Mar 13, 2026

Hilton Vacation Club Ocean Beach Club Virginia Beach
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 ...
8.8/10 Excellent! (3,753 reviews)
Great place loved the nostalgia

Reviewed on Mar 14, 2026

Schooner Inn
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! (658 reviews)
A/C was great

Reviewed on Mar 8, 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! (1,002 reviews)
Hotel was fine. They are currently under some remodeling and light construction I think, so there is some wear and tear showing in the elevators and the hallways, but the room was fine. The gym was nice and the pool appeared pleasant although we did not use it. The breakfast was good and selections ...

Reviewed on Mar 14, 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.