Cheap Flight Deals to Chesapeake VA from CA $71
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How to find cheap flights to Chesapeake?
The cheapest prices found with in the last 7 days for return flights were CA $143 and CA $71 for one-way flights to Chesapeake for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| JAX | Norfolk | September 23 to September 28 | CA $143 |
| MCO | Norfolk | September 10 to September 13 | CA $185 |
| TPA | Norfolk | September 11 to September 15 | CA $200 |
| ATL | Norfolk | September 1 to September 8 | CA $239 |
| SAN | Norfolk | November 7 to November 14 | CA $311 |
| BOS | Norfolk | September 16 to September 22 | CA $362 |
| DFW | Norfolk | October 23 to October 25 | CA $433 |
| SEA | Norfolk | September 28 to October 5 | CA $436 |
| LAX | Norfolk | September 18 to September 21 | CA $454 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| TPA | Norfolk | August 21 to August 23 | CA $469 |
| MCO | Norfolk | August 23 to August 30 | CA $505 |
| BOS | Norfolk | August 22 to August 24 | CA $515 |
| DFW | Norfolk | August 22 to August 26 | CA $588 |
| JAX | Norfolk | August 23 to August 25 | CA $639 |
| ATL | Norfolk | August 21 to August 24 | CA $799 |
| SEA | Norfolk | August 22 to August 29 | CA $839 |
Your guide to flights to Chesapeake, VA
Breeze Airways, WestJet fly to Chesapeake, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chesapeake VA currently costs between CA $143 and CA $839. Prices vary, but for the best fares, travel in September when prices are at their lowest.
Top tips for finding cheap flights to Chesapeake
The cheapest flight for a round trip to Chesapeake is currently CA $143. When you search for flights to Chesapeake, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chesapeake for nearby days. The cheapest month to travel to Chesapeake is September from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
How to cancel flights to Chesapeake
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
Why you should book your flight to Chesapeake with Travelocity
We have top deals on plane tickets even for last minute flights to Chesapeake, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Chesapeake for less.
Find The Perfect Hotel For After Your Flight
Amazing Place to Stay After Flight to Chesapeake
Comfort Suites Chesapeake - Norfolk
"Very clean, quiet and peaceful. Very welcoming"
Reviewed on Aug 19, 2026
WoodSpring Suites Chesapeake - Norfolk South
Comfort Inn & Suites Chesapeake - Portsmouth
"We stayed in the room for a total of 10 minutes. There was mold in the ceiling in the bathroom. There was body excrement on the wall behind the toilet. There was food splashed on the wall by a garbage can. The pull out bed had stains on the mattress and zero sheets. The lamp shades are all stained. ..."
Reviewed on Aug 17, 2026
Red Roof Inn Chesapeake Conference Center
"When looking somewhere to stay y’all should said in the booking site if it is a hotel or motel because if I know it was a motel I wouldn’t book the room and rooms need to be updated. Need iron in the rooms and more towels."
Reviewed on Aug 16, 2026
Our Top Chesapeake hotel with Airport Shuttles
Hilton Garden Inn Chesapeake/Greenbrier
Hyatt Place Chesapeake
"Love this Hotel clean, well located, the girl was helping with the breakfast was very helpful, clean area nice staff. The room very spacious. Indoor pool recommend it. I love Hyatt very different hotel, also the area is safe a lot of places to eat. free parking."
Reviewed on Aug 17, 2026
Luxury Hotels in Chesapeake
Aloft by Marriott Chesapeake
"We had a problem that they rectified within normal parameters at 12:30am in the morning."
Reviewed on Aug 17, 2026
Red Roof Inn Chesapeake Conference Center
"When looking somewhere to stay y’all should said in the booking site if it is a hotel or motel because if I know it was a motel I wouldn’t book the room and rooms need to be updated. Need iron in the rooms and more towels."
Reviewed on Aug 16, 2026
Hyatt Place Chesapeake
"Love this Hotel clean, well located, the girl was helping with the breakfast was very helpful, clean area nice staff. The room very spacious. Indoor pool recommend it. I love Hyatt very different hotel, also the area is safe a lot of places to eat. free parking."
Reviewed on Aug 17, 2026
Comfort Suites Chesapeake - Norfolk
"Very clean, quiet and peaceful. Very welcoming"
Reviewed on Aug 19, 2026
Family Friendly Hotels in Chesapeake
Hyatt Place Chesapeake
"Love this Hotel clean, well located, the girl was helping with the breakfast was very helpful, clean area nice staff. The room very spacious. Indoor pool recommend it. I love Hyatt very different hotel, also the area is safe a lot of places to eat. free parking."
Reviewed on Aug 17, 2026
Comfort Suites Chesapeake - Norfolk
"Very clean, quiet and peaceful. Very welcoming"
Reviewed on Aug 19, 2026
SpringHill Suites by Marriott Chesapeake Greenbrier
"This hotel was in such a convenient location, and the staff truly made our stay even better! The ladies at the front desk were absolutely amazing. Ms. Tiana and Ms. Crystal were always so helpful, polite, and welcoming. They greeted us with a smile and made sure we had everything we needed throughout ..."
Reviewed on Aug 19, 2026
Aloft by Marriott Chesapeake
"We had a problem that they rectified within normal parameters at 12:30am in the morning."
Reviewed on Aug 17, 2026
Need a car after flight to Chesapeake?
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Flights To Chesapeake
If a peaceful getaway is what you're seeking, you'll find it in historic Chesapeake, Virginia. Flights to Chesapeake land at the nearby Norfolk International Airport (ORF), in the heart of Virginia's coastal area, putting you in the perfect setting for laid-back family vacations or romantic getaway packages in Chesapeake. From beach lovers to history lovers to food lovers, this low-key locale has something for everyone to enjoy.
Transportation from ORF
The Coastal Virginia region is served by Norfolk International Airport, located 16 miles northeast of Chesapeake. By using one of several ground transportation options at ORF, you can easily reach your hotel and area attractions. Book reservations before traveling for airport shuttle service between Norfolk International and Chesapeake, or arrange for a rental car with one of the on-site car rental agencies, located near baggage claim below the terminal lobby. Taxi service is available outside the baggage claim lobby. If you're staying near ORF, check the reservation kiosks in the arrivals terminal for information regarding shuttle service from area hotels.
Enter Virginia's Gateway to Fun
Let Chesapeake be your home base for your Virginia vacation. Centrally located in the Coastal Virginia area, you'll have easy access to Chesapeake Bay and the Atlantic Ocean. Spend a day at the lush Great Dismal Swamp Wildlife Refuge hiking, biking, and watching wildlife, or fishing and boating on Lake Drummond. Learn more about the Commonwealth of Virginia when you visit historic American landmarks and attractions such as Colonial Williamsburg and Nauticus battleship tours. Wrap up a busy day of sightseeing and museum hopping with a sunset sail on Elizabeth River and a soul food feast at one of Chesapeake's favorite locally owned diners.
Ready to stay and play? Travelocity will help you find great deals on hotels in Chesapeake. Get mobile exclusive deals on the Travelocity app and save instantly on Chesapeake flights and hotels. Book your Chesapeake tickets now and you'll soon find out why they say Virginia is for lovers.
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