Search Cheap Flights to
Chesapeake

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chesapeake Flights as Low as $135

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

Frontier Airlines
Wed, Oct 28 - Sat, Nov 7
MCO
Orlando Intl.
ORF
Norfolk Intl.
$135 Roundtrip, just found
$135
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Oct 28 from Orlando Intl. to Norfolk Intl., returning Sat, Nov 7, priced at $135 just found
Breeze Airways
Tue, Nov 10 - Mon, Nov 16
MCO
Orlando Intl.
ORF
Norfolk Intl.
$179 Roundtrip, found 19 hours ago
$179
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Tue, Nov 10 from Orlando Intl. to Norfolk Intl., returning Mon, Nov 16, priced at $179 found 19 hours ago
Frontier Airlines
Sat, Oct 24 - Tue, Oct 27
DTW
Detroit Metropolitan Wayne County
ORF
Norfolk Intl.
$224 Roundtrip, just found
$224
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 24 from Detroit Metropolitan Wayne County to Norfolk Intl., returning Tue, Oct 27, priced at $224 just found
Southwest Airlines
Wed, Oct 28 - Sat, Nov 7
MCO
Orlando Intl.
ORF
Norfolk Intl.
$301 Roundtrip, just found
$301
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Oct 28 from Orlando Intl. to Norfolk Intl., returning Sat, Nov 7, priced at $301 just found
Delta
Wed, Oct 28 - Sat, Nov 7
MCO
Orlando Intl.
ORF
Norfolk Intl.
$311 Roundtrip, just found
$311
Roundtrip
just found
Select Delta flight, departing Wed, Oct 28 from Orlando Intl. to Norfolk Intl., returning Sat, Nov 7, priced at $311 just found
American Airlines
Wed, Oct 28 - Sat, Nov 7
MCO
Orlando Intl.
ORF
Norfolk Intl.
$311 Roundtrip, just found
$311
Roundtrip
just found
Select American Airlines flight, departing Wed, Oct 28 from Orlando Intl. to Norfolk Intl., returning Sat, Nov 7, priced at $311 just found
United
Wed, Oct 28 - Sat, Nov 7
MCO
Orlando Intl.
ORF
Norfolk Intl.
$311 Roundtrip, just found
$311
Roundtrip
just found
Select United flight, departing Wed, Oct 28 from Orlando Intl. to Norfolk Intl., returning Sat, Nov 7, priced at $311 just found
Bargain Flight
Tue, Oct 20 - Tue, Oct 27
LAX
Los Angeles Intl.
ORF
Norfolk Intl.
$331 Roundtrip, just found
$331
Roundtrip
just found
Select Bargain Flight flight, departing Tue, Oct 20 from Los Angeles Intl. to Norfolk Intl., returning Tue, Oct 27, priced at $331 just found
Bargain Flight
Tue, Oct 20 - Tue, Oct 27
SAN
San Diego Intl.
ORF
Norfolk Intl.
$335 Roundtrip, just found
$335
Roundtrip
just found
Select Bargain Flight flight, departing Tue, Oct 20 from San Diego Intl. to Norfolk Intl., returning Tue, Oct 27, priced at $335 just found
American Airlines
Tue, Oct 20 - Mon, Oct 26
MCO
Orlando Intl.
PHF
Newport News - Williamsburg Intl.
$437 Roundtrip, just found
$437
Roundtrip
just found
Select American Airlines flight, departing Tue, Oct 20 from Orlando Intl. to Newport News - Williamsburg Intl., returning Mon, Oct 26, priced at $437 just found
American Airlines
Wed, Nov 11 - Sat, Nov 14
LAX
Los Angeles Intl.
PHF
Newport News - Williamsburg Intl.
$441 Roundtrip, just found
$441
Roundtrip
just found
Select American Airlines flight, departing Wed, Nov 11 from Los Angeles Intl. to Newport News - Williamsburg Intl., returning Sat, Nov 14, priced at $441 just found
American Airlines
Thu, Nov 19 - Wed, Dec 9
SAN
San Diego Intl.
PHF
Newport News - Williamsburg Intl.
$497 Roundtrip, just found
$497
Roundtrip
just found
Select American Airlines flight, departing Thu, Nov 19 from San Diego Intl. to Newport News - Williamsburg Intl., returning Wed, Dec 9, priced at $497 just found
American Airlines
Thu, Oct 22 - Mon, Oct 26
DTW
Detroit Metropolitan Wayne County
PHF
Newport News - Williamsburg Intl.
$565 Roundtrip, just found
$565
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct 22 from Detroit Metropolitan Wayne County to Newport News - Williamsburg Intl., returning Mon, Oct 26, priced at $565 just found
American Airlines
Wed, Oct 21 - Sun, Oct 25
CLD
McClellan-Palomar
ORF
Norfolk Intl.
$568 Roundtrip, just found
$568
Roundtrip
just found
Select American Airlines flight, departing Wed, Oct 21 from McClellan-Palomar to Norfolk Intl., returning Sun, Oct 25, priced at $568 just found
American Airlines
Thu, Nov 19 - Wed, Dec 9
CLD
McClellan-Palomar
PHF
Newport News - Williamsburg Intl.
$585 Roundtrip, just found
$585
Roundtrip
just found
Select American Airlines flight, departing Thu, Nov 19 from McClellan-Palomar to Newport News - Williamsburg Intl., returning Wed, Dec 9, priced at $585 just found
American Airlines
Tue, Nov 10 - Wed, Nov 11
ONT
Ontario Intl. Airport
PHF
Newport News - Williamsburg Intl.
$1,010 Roundtrip, just found
$1,010
Roundtrip
just found
Select American Airlines flight, departing Tue, Nov 10 from Ontario Intl. Airport to Newport News - Williamsburg Intl., returning Wed, Nov 11, priced at $1,010 just found

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 October, 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 14 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 $135, 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 $135 right now, why wait?

Chesapeake Flight Information
Destination airport
Norfolk Intl.
Destination airport IATA code
ORF
Roundtrip price
$135

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 ...
8.8/10 Excellent! (1,068 reviews)
"The place was clean and smelled amazing. It was quiet and staff was friendly and helpful."

Reviewed on Aug 28, 2026

Get rates
Comfort Suites Chesapeake - Norfolk
Ocean Resort

Ocean Resort

2.5 out of 5
Atlantic Avenue,2417 Virginia Beach VA
Stay at this hotel in Virginia Beach. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
7.8/10 Good! (1,724 reviews)
"There was a leak in the bedroom area and it didn’t get fixed at all even though we asked staff about it. Doorknob in the bathroom was broken and the sound curtain didn’t have the plastic so water got all over the bathroom."

Reviewed on Aug 29, 2026

Get rates
Ocean Resort
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
4453 Bonney Rd Virginia Beach VA
Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
8.4/10 Very Good! (532 reviews)
"Best hotel i have stayed in a very very long time. Amazing place"

Reviewed on Aug 29, 2026

Get rates
Crowne Plaza Virginia Beach Town Center by IHG
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Stay at this hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. ...
Get rates
Wyndham Virginia Beach Oceanfront
Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
3900 Atlantic Avenue Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (1,505 reviews)
"Kids pool is very nice."

Reviewed on Aug 27, 2026

Get rates
Holiday Inn & Suites Virginia Beach North Beach by IHG
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
Book a stay at this 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! (1,502 reviews)
"The hotel was excellent. Customer service was great"

Reviewed on Aug 28, 2026

Get rates
Delta Hotels by Marriott Virginia Beach Waterfront Suites
Holiday Inn Va Beach-Oceanside (21st St) by IHG

Holiday Inn Va Beach-Oceanside (21st St) by IHG

3 out of 5
2101 Atlantic Avenue Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
9/10 Wonderful! (1,092 reviews)
"We booked two rooms, and unfortunately, the overall experience was quite disappointing. The toilet in one of the rooms stopped working. Maintenance came and fixed it once, but unfortunately, it broke again. In the room where my mom stayed, the central air conditioning was also not functioning properly, ..."

Reviewed on Aug 28, 2026

Get rates
Holiday Inn Va Beach-Oceanside (21st St) by IHG
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 ...
Get rates
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
See all 3,494 properties in 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.

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 ...
Get rates
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! (1,001 reviews)
"The room had bugs. The room number was literally a cardboard cutout with sharpie on it. The carpet was stained. Charge us $30 extra for a 4th floor room that had a view of dumpsters in the parking lot. Put $150 hold for incidentals that that hold for 5 days without any charges. No creamer for in ..."

Reviewed on Aug 26, 2026

Get rates
Hyatt Place Chesapeake
See all 3,494 properties in 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.