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Chesapeake

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Chesapeake Flights as Low as $63

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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 February, 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 $63, 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 $63 right now, why wait?

Chesapeake Flight Information
Destination airport
Norfolk Intl.
Destination airport IATA code
ORF
Roundtrip price
$129

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 ...
7.8/10 Good! (1,003 reviews)
Room was clean lobby was cllean ample parking

Reviewed on Jan 21, 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 ...
8.6/10 Excellent! (1,016 reviews)
Staff was amazing

Reviewed on Jan 20, 2026

Comfort Suites Chesapeake - Norfolk
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)
Clean rooms, nice stuff

Reviewed on Jan 15, 2026

Holiday Inn Express Chesapeake - Norfolk by IHG
Fairfield Inn and Suites By Marriott Chesapeake

Fairfield Inn and Suites By Marriott Chesapeake

2.5 out of 5
1560 Crossways Blvd Chesapeake VA
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,002 reviews)
Check in was easy, room is perfect for our needs and staff has been exceptionally pleasant and helpful.

Reviewed on Jan 14, 2026

Fairfield Inn and Suites By Marriott Chesapeake
WoodSpring Suites Chesapeake - Norfolk South

WoodSpring Suites Chesapeake - Norfolk South

2.5 out of 5
137 Kempsville Rd Chesapeake VA
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our ...
5.8/10 (658 reviews)
Staff was really welcoming and nice.. I plan on returning.

Reviewed on Dec 8, 2025

WoodSpring Suites Chesapeake - Norfolk South
Extended Stay America Suites Chesapeake Crossways Blvd

Extended Stay America Suites Chesapeake Crossways Blvd

2.5 out of 5
1540 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 in our reviews. ...
6.4/10 (1,002 reviews)
Flawless room

Reviewed on Jan 13, 2026

Extended Stay America Suites Chesapeake Crossways Blvd
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 ...
9.2/10 Wonderful! (2,200 reviews)
Everything was so perfect, clean and nice views!

Reviewed on Jan 22, 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 ...
8.2/10 Very Good! (2,495 reviews)
Our room was clean!

Reviewed on Jan 19, 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! (653 reviews)
Room was spotless and staff was excellent!

Reviewed on Jan 15, 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)
Clean and very neat

Reviewed on Jan 11, 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.