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Chesapeake

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Chesapeake Flights as Low as $140

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

Delta
Tue, Oct 21 - Sat, Oct 25
BOS
Logan Intl.
ORF
Norfolk Intl.
$140 Roundtrip, found 14 hours ago
$140
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Oct 21 from Logan Intl. to Norfolk Intl., returning Sat, Oct 25, priced at $140 found 14 hours ago
JetBlue Airways
Tue, Oct 21 - Sat, Oct 25
BOS
Logan Intl.
ORF
Norfolk Intl.
$140 Roundtrip, found 14 hours ago
$140
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Logan Intl. to Norfolk Intl., returning Sat, Oct 25, priced at $140 found 14 hours ago
JetBlue Airways
Sun, Sep 21 - Wed, Sep 24
BOS
Logan Intl.
ORF
Norfolk Intl.
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Sep 21 from Logan Intl. to Norfolk Intl., returning Wed, Sep 24, priced at $145 found 5 days ago
JetBlue Airways
Sun, Sep 21 - Tue, Sep 23
BOS
Logan Intl.
ORF
Norfolk Intl.
$150 Roundtrip, found 5 days ago
$150
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Sep 21 from Logan Intl. to Norfolk Intl., returning Tue, Sep 23, priced at $150 found 5 days ago
United
Wed, Sep 17 - Tue, Sep 23
BOS
Logan Intl.
ORF
Norfolk Intl.
$159 Roundtrip, found 17 hours ago
$159
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Sep 17 from Logan Intl. to Norfolk Intl., returning Tue, Sep 23, priced at $159 found 17 hours ago
JetBlue Airways
Tue, Oct 21 - Sat, Oct 25
BOS
Logan Intl.
ORF
Norfolk Intl.
$160 Roundtrip, found 14 hours ago
$160
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Logan Intl. to Norfolk Intl., returning Sat, Oct 25, priced at $160 found 14 hours ago
American Airlines
Tue, Oct 21 - Sat, Oct 25
BOS
Logan Intl.
ORF
Norfolk Intl.
$161 Roundtrip, found 14 hours ago
$161
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Oct 21 from Logan Intl. to Norfolk Intl., returning Sat, Oct 25, priced at $161 found 14 hours ago
JetBlue Airways
Sun, Oct 19 - Sat, Oct 25
BOS
Logan Intl.
ORF
Norfolk Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Oct 19 from Logan Intl. to Norfolk Intl., returning Sat, Oct 25, priced at $167 found 4 days ago
American Airlines
Wed, Sep 17 - Tue, Sep 23
BOS
Logan Intl.
ORF
Norfolk Intl.
$169 Roundtrip, found 17 hours ago
$169
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Sep 17 from Logan Intl. to Norfolk Intl., returning Tue, Sep 23, priced at $169 found 17 hours ago
JetBlue Airways
Sun, Sep 14 - Sat, Sep 20
BOS
Logan Intl.
ORF
Norfolk Intl.
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Sep 14 from Logan Intl. to Norfolk Intl., returning Sat, Sep 20, priced at $170 found 1 day ago
Delta
Fri, Oct 24 - Sat, Oct 25
BOS
Logan Intl.
ORF
Norfolk Intl.
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Oct 24 from Logan Intl. to Norfolk Intl., returning Sat, Oct 25, priced at $177 found 4 days ago
United
Thu, Sep 18 - Tue, Sep 23
BOS
Logan Intl.
ORF
Norfolk Intl.
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Select United flight, departing Thu, Sep 18 from Logan Intl. to Norfolk Intl., returning Tue, Sep 23, priced at $178 found 6 days ago
United
Wed, Sep 17 - Tue, Sep 23
BOS
Logan Intl.
ORF
Norfolk Intl.
$179 Roundtrip, found 17 hours ago
$179
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Sep 17 from Logan Intl. to Norfolk Intl., returning Tue, Sep 23, priced at $179 found 17 hours ago
Spirit Airlines
Wed, Oct 22 - Mon, Oct 27
BWI
Baltimore Washington Intl. Thurgood Marshall
ORF
Norfolk Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Oct 22 from Baltimore Washington Intl. Thurgood Marshall to Norfolk Intl., returning Mon, Oct 27, priced at $217 found 1 hour ago
American Airlines
Fri, Aug 29 - Sun, Aug 31
BOS
Logan Intl.
PHF
Newport News - Williamsburg Intl.
$402 Roundtrip, found 1 day ago
$402
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 29 from Logan Intl. to Newport News - Williamsburg Intl., returning Sun, Aug 31, priced at $402 found 1 day ago
American Airlines
Tue, Sep 9 - Tue, Sep 16
BWI
Baltimore Washington Intl. Thurgood Marshall
PHF
Newport News - Williamsburg Intl.
$598 Roundtrip, found 9 hours ago
$598
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 9 from Baltimore Washington Intl. Thurgood Marshall to Newport News - Williamsburg Intl., returning Tue, Sep 16, priced at $598 found 9 hours 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 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 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 $140, 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 $140 right now, why wait?

Chesapeake Flight Information
Destination airport
Norfolk Intl.
Destination airport IATA code
ORF
Roundtrip price
$139

Last Minute Hotel Deals in Chesapeake

STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy, Chesapeake, VA
Stay at this hotel in Chesapeake. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.6/10 (527 reviews)
Great place at a great price
"I had a great stay at Studios & Suites for Less. The staff is really nice and helpful. The room was super nice: clean, spacious, with a fridge and microwave. It was exactly what I needed for a week-long business trip, and the price was super affordable."

Reviewed on Aug 25, 2025

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STUDIOS & SUITES 4 LESS CHESAPEAKE
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
Stay at this 3-star 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! (2,267 reviews)
"Amazing stay. We have a special needs child and staff was very understanding and kind."

Reviewed on Aug 25, 2025

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Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Stay at this 3-star beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,095 reviews)
Budget Friendly
"Stay was fine for a short weekend getaway. Hotel is older and run down but all rooms have ocean facing balconies. There is a small pool but no where near there size needed for an hotel this size. Easy access to the beach and boardwalk. Our toilet didn’t work and ran all weekend and parking is down ..."

Reviewed on Aug 25, 2025

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Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 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 restaurant and the helpful staff ...
7.6/10 Good! (1,642 reviews)
"Ok"

Reviewed on Aug 23, 2025

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Wyndham Virginia Beach Oceanfront
DoubleTree by Hilton Virginia Beach

DoubleTree by Hilton Virginia Beach

4 out of 5
1900 Pavilion Dr, Virginia Beach, VA
Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,006 reviews)
"The hole site good customer service"

Reviewed on Aug 23, 2025

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DoubleTree by Hilton Virginia Beach
Hyatt Place Virginia Beach Town Center

Hyatt Place Virginia Beach Town Center

3 out of 5
335 Independence Blvd, Virginia Beach, VA
Stay at this 3-star business-friendly hotel in Virginia Beach. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and ...
9/10 Wonderful! (1,002 reviews)
It made for a trip that was fine
"The facility was fine. It was a convenient location for us as we visited family who live at the beach. We didn't need anything ocean front, so it was a little less expensive than being right on the beach. The bed was very uncomfortable and didn't provide a great opportunity for rest. There is not ..."

Reviewed on Aug 21, 2025

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Hyatt Place Virginia Beach Town Center
Oceans 2700

Oceans 2700

2.5 out of 5
2700 Pacific Avenue, Virginia Beach, VA
Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
8/10 Very Good! (1,389 reviews)
"The staff is wonderful! Very accommodating and pleasant!"

Reviewed on Aug 22, 2025

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Oceans 2700
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
Stay at this 3-star 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 ...
7.8/10 Good! (1,036 reviews)
"Staff was amazing. Very clean. I will definitely be staying there again."

Reviewed on Aug 23, 2025

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Holiday Inn & Suites Virginia Beach North Beach by IHG
See all 3,420 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
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 ...
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Hilton Garden Inn Chesapeake/Greenbrier
Hyatt Place Chesapeake

Hyatt Place Chesapeake

3 out of 5
709 Eden Way N, Chesapeake, VA
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 ...
8.4/10 Very Good! (1,002 reviews)
"It was nice"

Reviewed on Aug 23, 2025

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Hyatt Place Chesapeake
See all 3,420 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.