$46 Cheap flight deals from Boston (BOS) to Chesapeake (PHF)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Boston to Chesapeake

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Nov 21 - Fri, Nov 21
PVD
T.F. Green
ORF
Norfolk Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Nov 21 from T.F. Green to Norfolk Intl., returning Fri, Nov 21, priced at $193 found 1 day ago
Sun, Nov 23 - Fri, Nov 28
BOS
Logan Intl.
ORF
Norfolk Intl.
$328 Roundtrip, found 4 days ago
$328
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Nov 23 from Logan Intl. to Norfolk Intl., returning Fri, Nov 28, priced at $328 found 4 days ago
Sat, Nov 22 - Fri, Nov 28
MHT
Manchester-Boston Regional
ORF
Norfolk Intl.
$347 Roundtrip, found 4 days ago
$347
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 22 from Manchester-Boston Regional to Norfolk Intl., returning Fri, Nov 28, priced at $347 found 4 days ago

Airfares from $46 One Way, $92 Round Trip from Boston to Chesapeake

Prices starting at $92 for return flights and $46 for one-way flights to Chesapeake were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Jan 22 - Sun, Jan 25
PVD
Providence
ORF
Norfolk
$92 Roundtrip, found 5 hours ago
$92
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Jan 22 from Providence to Norfolk, returning Sun, Jan 25, priced at $92 found 5 hours ago
Fri, Jan 23 - Fri, Jan 30
BOS
Boston
ORF
Norfolk
$129 Roundtrip, found 5 hours ago
$129
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Fri, Jan 23 from Boston to Norfolk, returning Fri, Jan 30, priced at $129 found 5 hours ago
Thu, Mar 26 - Wed, Apr 1
BOS
Boston
ORF
Norfolk
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Boston to Norfolk, returning Wed, Apr 1, priced at $157 found 3 hours ago
Wed, Dec 3 - Wed, Dec 10
BOS
Boston
ORF
Norfolk
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Dec 3 from Boston to Norfolk, returning Wed, Dec 10, priced at $177 just found
Wed, Dec 3 - Wed, Dec 10
BOS
Boston
ORF
Norfolk
$177 Roundtrip, just found
$177
Roundtrip
just found
Select American Airlines flight, departing Wed, Dec 3 from Boston to Norfolk, returning Wed, Dec 10, priced at $177 just found

Chesapeake economy flight packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas
3.0-star property

Boardwalk Resort and Villas

17.2/10 Exceptional! (1,003 reviews)

Jan 2 - Jan 5

3 night stay

Boston (BOS) to Norfolk (ORF)

United • Non-stop roundtrip • Coach
Price was $389, price is now $311 per person
$311
per person
found 1 day ago
The room was very nice and updated.The room was a lot smaller in person versus the pictures before booking but still nice. The hot tub was out of order when I was there so we weren't able to use it. The staff was very friendly and always greeted you throughout the stay. Also I can't comment on a beach view because we had the city view which was still nice but I would have preferred having a room with a balcony. If I would have known the city view didn't have a balcony I would have paid a couple bucks more to get it. Nice stay considering the not so good weather.

Reviewed on Oct 18, 2025

The Colony at Virginia Beach
2.5-star property

The Colony at Virginia Beach

16/10 Exceptional! (6 reviews)

Dec 29 - Jan 3

5 night stay

Boston (BOS) to Norfolk (ORF)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $740, price is now $559 per person
$559
per person
found 21 hours ago
Delta Hotels by Marriott Virginia Beach Waterfront Suites
4.0-star property

Delta Hotels by Marriott Virginia Beach Waterfront Suites

16.8/10 Exceptional! (1,434 reviews)

Jan 2 - Jan 5

3 night stay

Boston (BOS) to Norfolk (ORF)

United • Non-stop roundtrip • Coach
Price was $439, price is now $338 per person
$338
per person
found 1 day ago
BEAUTIFUL beach. Best beach spot in Virginia Beach. However, the quality of service in this hotel seriously declined. I’ve been coming here for years, and this year was significantly worse than ever before. The cleanliness in the rooms is substandard, the lines at the front desk are excessive. It took 2 to 3 hours to get bedding sent to the room each time I’ve requested (3 times over 2 trips this month). I visited twice this month because the beach is so beautiful, but I’m not sure I’ll be going back next year because the service quality has diminished so much. Time to look around.

Reviewed on Aug 31, 2025

Don't see what you're looking for?
See all available trips from Boston to Chesapeake
View all trips

More About Flying To Chesapeake from Boston

Route Information for Flights from Boston to Chesapeake

Origin Airport IATA Code
BOS
Destination Airport IATA Code
PHF
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Boston to Chesapeake

If you have been putting off a well-deserved vacation due to a tight budget, now is the time to visit Orbitz.com. We offer you huge savings on Boston to Chesapeake flights, great hotel rooms, and stellar vacation packages. Let Orbitz show you how to cheaply plan the perfect trip.

Guaranteed low prices on flights from Boston to Chesapeake

Low fares, discounted rates, great deals, and special promotions—all of these can be found through Orbitz. Get cheap fares on Boston to Chesapeake flights and amazing deals on luxury hotels. You can even accumulate loyalty or frequent flyer miles or points on qualifying flights from Boston to Chesapeake so you can earn flight rewards on your favorite airlines.

Mobile planning for flights from Boston to Chesapeake

Worried about unexpected flight delays or other travel disruptions on your Boston to Chesapeake flights? You can opt to receive free alerts sent to you and six of your contacts via email, voicemail, or text. The Orbitz mobile app also lets you access up-to-date flight information from your iPhone, iPad, and mobile Android devices. Our mobile technology let you check baggage claim and gate details, view your itinerary for your flights from Boston to Chesapeake, and book exclusive hotel deals—even on the same day.

Take advantage of low fares on Boston to Chesapeake flights and vacation packages

Orbitz has the best prices available on flights from Boston to Chesapeake. Take advantage of our low fare sales and discounts and begin to plan your next trip. We also give you great savings on hotels, car rentals, and vacation packages.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.