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 $107

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

Breeze Airways
Thu, May 29 - Mon, Jun 2
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$107 Roundtrip, found 6 days ago
$107
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 29 from Jacksonville Intl. to Norfolk Intl., returning Mon, Jun 2, priced at $107 found 6 days ago
Breeze Airways
Thu, May 29 - Mon, Jun 2
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$112 Roundtrip, found 6 days ago
$112
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 29 from Jacksonville Intl. to Norfolk Intl., returning Mon, Jun 2, priced at $112 found 6 days ago
Breeze Airways
Thu, May 29 - Mon, Jun 2
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 29 from Jacksonville Intl. to Norfolk Intl., returning Mon, Jun 2, priced at $117 found 6 days ago
Breeze Airways
Thu, Jul 3 - Tue, Jul 8
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$147 Roundtrip, found 18 hours ago
$147
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Jul 3 from Jacksonville Intl. to Norfolk Intl., returning Tue, Jul 8, priced at $147 found 18 hours ago
Spirit Airlines
Sun, May 25 - Thu, May 29
FLL
Fort Lauderdale - Hollywood Intl.
ORF
Norfolk Intl.
$150 Roundtrip, found 3 days ago
$150
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, May 25 from Fort Lauderdale - Hollywood Intl. to Norfolk Intl., returning Thu, May 29, priced at $150 found 3 days ago
Breeze Airways
Thu, Jul 3 - Tue, Jul 8
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$152 Roundtrip, found 18 hours ago
$152
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Jul 3 from Jacksonville Intl. to Norfolk Intl., returning Tue, Jul 8, priced at $152 found 18 hours ago
Breeze Airways
Thu, Jul 3 - Tue, Jul 8
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$157 Roundtrip, found 18 hours ago
$157
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Jul 3 from Jacksonville Intl. to Norfolk Intl., returning Tue, Jul 8, priced at $157 found 18 hours ago
Frontier Airlines
Sun, May 25 - Thu, May 29
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$171 Roundtrip, found 1 hour ago
$171
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, May 25 from Dallas-Fort Worth Intl. to Norfolk Intl., returning Thu, May 29, priced at $171 found 1 hour ago
Delta
Tue, May 20 - Wed, May 28
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, May 20 from Jacksonville Intl. to Norfolk Intl., returning Wed, May 28, priced at $230 found 2 days ago
American Airlines
Sat, May 17 - Tue, May 20
SYR
Hancock Intl.
PHF
Newport News - Williamsburg Intl.
$233 Roundtrip, found 22 hours ago
$233
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, May 17 from Hancock Intl. to Newport News - Williamsburg Intl., returning Tue, May 20, priced at $233 found 22 hours ago
United
Wed, Jul 2 - Mon, Jul 7
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$272 Roundtrip, found 18 hours ago
$272
Roundtrip
found 18 hours ago
Select United flight, departing Wed, Jul 2 from Jacksonville Intl. to Norfolk Intl., returning Mon, Jul 7, priced at $272 found 18 hours ago
Delta
Tue, May 27 - Thu, May 29
DAL
Love Field
ORF
Norfolk Intl.
$311 Roundtrip, found 1 hour ago
$311
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, May 27 from Love Field to Norfolk Intl., returning Thu, May 29, priced at $311 found 1 hour ago
American Airlines
Fri, Jun 13 - Mon, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
PHF
Newport News - Williamsburg Intl.
$332 Roundtrip, found 1 day ago
$332
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jun 13 from Fort Lauderdale - Hollywood Intl. to Newport News - Williamsburg Intl., returning Mon, Jun 16, priced at $332 found 1 day ago
American Airlines
Wed, Jul 2 - Mon, Jul 7
JAX
Jacksonville Intl.
PHF
Newport News - Williamsburg Intl.
$347 Roundtrip, found 18 hours ago
$347
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Wed, Jul 2 from Jacksonville Intl. to Newport News - Williamsburg Intl., returning Mon, Jul 7, priced at $347 found 18 hours ago
American Airlines
Sat, May 10 - Tue, May 13
DFW
Dallas-Fort Worth Intl.
PHF
Newport News - Williamsburg Intl.
$604 Roundtrip, found 1 day ago
$604
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, May 10 from Dallas-Fort Worth Intl. to Newport News - Williamsburg Intl., returning Tue, May 13, priced at $604 found 1 day ago
JetBlue Airways
Fri, May 2 - Mon, May 5
FLL
Fort Lauderdale - Hollywood Intl.
ORF
Norfolk Intl.
$671 Roundtrip, found 2 days ago
$671
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, May 2 from Fort Lauderdale - Hollywood Intl. to Norfolk Intl., returning Mon, May 5, priced at $671 found 2 days ago

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 May, 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 $107, 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 $107 right now, why wait?

Chesapeake Flight Information
Destination airport
Norfolk Intl.
Destination airport IATA code
ORF
Roundtrip price
$106

Last Minute Hotel Deals in Chesapeake

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
The price is $110 per night from May 11 to May 12
$110
includes taxes & fees
May 11 - May 12
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)
"We liked everything"

Reviewed on Apr 21, 2025

Holiday Inn Express Chesapeake - Norfolk by IHG
TRU by Hilton Chesapeake, VA
TRU by Hilton Chesapeake, VA
2.5 out of 5
1570 CROSSWAYS BLVD, Chesapeake, VA
The price is $122 per night from Apr 27 to Apr 28
$122
includes taxes & fees
Apr 27 - Apr 28
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 ...
8.8/10 Excellent! (174 reviews)
"Nice hotel"

Reviewed on Apr 23, 2025

TRU by Hilton Chesapeake, VA
Wingate by Wyndham Chesapeake
Wingate by Wyndham Chesapeake
2.5 out of 5
817 Greenbrier Circle, Chesapeake, VA
The price is $109 per night from Apr 29 to Apr 30
$109
includes taxes & fees
Apr 29 - Apr 30
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! (1,001 reviews)
Don’t skip this hotel!!
"We loved our stay. The breakfast is where this hotel shines. My daughter who is only a morning herbal tea drinker was impressed there was something other than black tea. This is now our new monthly hotel when we go for hockey games!"

Reviewed on Apr 21, 2025

Wingate by Wyndham Chesapeake
Hyatt Place Virginia Beach / Oceanfront
Hyatt Place Virginia Beach / Oceanfront
3 out of 5
3601 ATLANTIC AVENUE, 36TH AND ATLANTIC, Virginia Beach, VA
The price is $186 per night from Apr 30 to May 1
$186
includes taxes & fees
Apr 30 - May 1
Stay at this 3-star 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! (1,793 reviews)
"We had a great stay and really enjoyed the view and location!"

Reviewed on Apr 24, 2025

Hyatt Place Virginia Beach / Oceanfront
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
3 out of 5
1801 Atlantic Ave, Virginia Beach, VA
The price is $129 per night from Apr 27 to Apr 28
$129
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
8/10 Very Good! (2,086 reviews)
"Comfortable stay. Odd set up of pull out (by door, very loud)"

Reviewed on Apr 22, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Wyndham Virginia Beach Oceanfront
Wyndham Virginia Beach Oceanfront
3 out of 5
5700 Atlantic Ave, Virginia Beach, VA
The price is $112 per night from May 4 to May 5
$112
includes taxes & fees
May 4 - May 5
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 ...
7.4/10 Good! (1,462 reviews)
"."

Reviewed on Apr 22, 2025

Wyndham Virginia Beach Oceanfront
Hilton Virginia Beach Oceanfront
Hilton Virginia Beach Oceanfront
4 out of 5
3001 Atlantic Ave, Virginia Beach, VA
The price is $191 per night from Apr 27 to Apr 28
$191
includes taxes & fees
Apr 27 - Apr 28
Stay at this 4-star beach resort in Virginia Beach. Enjoy an outdoor pool, a beach locale, and 3 bars/lounges. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,002 reviews)
"The outdoor pool was nice but the indoor was a little smelly. Overall stay was good."

Reviewed on Apr 22, 2025

Hilton Virginia Beach Oceanfront
Schooner Inn
Schooner Inn
2 out of 5
215 Atlantic Ave, Virginia Beach, VA
The price is $71 per night from Apr 27 to Apr 28
$71
includes taxes & fees
Apr 27 - Apr 28
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! (3,012 reviews)
"Love the tub😍😍😍"

Reviewed on Apr 22, 2025

Schooner Inn
See all 3,453 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
The price is $130 per night from Apr 27 to Apr 28
$130
includes taxes & fees
Apr 27 - Apr 28
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! (605 reviews)
"The room was very spacious."

Reviewed on Apr 7, 2025

Hilton Garden Inn Chesapeake/Greenbrier
Hyatt Place Chesapeake
Hyatt Place Chesapeake
3 out of 5
709 Eden Way N, Chesapeake, VA
The price is $138 per night from Apr 27 to Apr 28
$138
includes taxes & fees
Apr 27 - Apr 28
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 ...
8.2/10 Very Good! (1,006 reviews)
"Clean rooms and professional personal!"

Reviewed on Apr 20, 2025

Hyatt Place Chesapeake
See all 3,453 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.