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Chesapeake

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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 , 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  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 , 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  right now, why wait?

Chesapeake Flight Information
Destination airport
Norfolk Intl.
Destination airport IATA code
ORF
Roundtrip price
$337

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 ...
8.4/10 Very Good! (1,009 reviews)
Clean rooms and good staff.

Reviewed on Nov 9, 2025

Comfort Suites Chesapeake - Norfolk
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 ...
8/10 Very Good! (1,001 reviews)
The room was pretty clean. Good breakfast.

Reviewed on Nov 1, 2025

Wingate by Wyndham Chesapeake
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, 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 ...
6.8/10 (1,000 reviews)
Amazing staff. Clean rooms. But other guest were smoking weed and you could smell it in our room all night.

Reviewed on Oct 26, 2025

Red Roof Inn Chesapeake Conference Center
Aloft Chesapeake

Aloft Chesapeake

3 out of 5
1454 Crossways Boulevard, Chesapeake, VA
Stay at this 3-star business-friendly hotel in Chesapeake. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,002 reviews)
Great rooms very clean

Reviewed on Nov 5, 2025

Aloft 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
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! (1,000 reviews)
Spotless room, quality linens, very friendly staff!!

Reviewed on Nov 1, 2025

Holiday Inn Express Chesapeake - Norfolk by IHG
Schooner Inn

Schooner Inn

2 out of 5
215 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 convenient ...
8.6/10 Excellent! (3,631 reviews)
I love saying

Reviewed on Nov 9, 2025

Schooner Inn
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
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! (2,406 reviews)
Everything about the room and the hotel was perfect.

Reviewed on Nov 7, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
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! (1,000 reviews)
Hotel was nice and clean. Located in a great location. Close to everything I needed. Room was nice. There was a small area in the ceiling that needed repairs. Loved the bathroom. Breakfast was tasty. It was worth $11.

Reviewed on Nov 4, 2025

Hyatt Place Virginia Beach Town Center
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 ...
7.8/10 Good! (649 reviews)
Yes

Reviewed on Oct 20, 2025

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! (1,001 reviews)
Rooms was very comfortable

Reviewed on Nov 6, 2025

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.