Cheap Flight Deals to Chesapeake VA from CA $130

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Chesapeake?

The cheapest prices found with in the last 7 days for return flights were CA $231 and CA $130 for one-way flights to Chesapeake for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSNorfolkJune 10 to June 19CA $231
ATLNorfolkJune 16 to July 3CA $282
LAXNorfolkJuly 12 to July 19CA $411
SEANorfolkJuly 18 to August 3CA $912
*Prices include taxes and fees

Your guide to flights to Chesapeake, VA

JetBlue Airways, Delta 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 $231 and CA $912. Prices vary, but for the best fares, travel in August 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 $231. 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 June 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

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
The price is CA $128 per night from Jun 4 to Jun 5
CA $128
CA $149 total
includes taxes & fees
Jun 4 - Jun 5
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 ...
8.2/10 Very Good! (1,007 reviews)
"Nice comfortable stay"

Reviewed on May 26, 2025

Comfort Suites Chesapeake - Norfolk
WoodSpring Suites Chesapeake - Norfolk South

WoodSpring Suites Chesapeake - Norfolk South

2.5 out of 5
137 Kempsville Rd, Chesapeake, VA
The price is CA $123 per night from Jun 1 to Jun 2
CA $123
CA $143 total
includes taxes & fees
Jun 1 - Jun 2
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our ...
5.8/10 (595 reviews)
"I've had a nice experience here overall. Shay at the front desk is wonderful and very helpful. I would definitely stay here again during my travels."

Reviewed on May 21, 2025

WoodSpring Suites Chesapeake - Norfolk South
Comfort Inn & Suites Chesapeake - Portsmouth

Comfort Inn & Suites Chesapeake - Portsmouth

2.5 out of 5
3355 S Military Hwy, Chesapeake, VA
The price is CA $108 per night from Jun 1 to Jun 2
CA $108
CA $142 total
includes taxes & fees
Jun 1 - Jun 2
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 ...
6.2/10 (873 reviews)
"Nice manager!"

Reviewed on May 19, 2025

Comfort Inn & Suites Chesapeake - Portsmouth
Save an average of 15% on thousands of hotels when you're signed in
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 ...
7/10 Good! (1,001 reviews)
"."

Reviewed on May 8, 2025

Red Roof Inn Chesapeake Conference 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.

Our Top Chesapeake hotel with Airport Shuttles

Hilton Garden Inn Chesapeake/Greenbrier

Hilton Garden Inn Chesapeake/Greenbrier

3 out of 5
1565 Crossways Blvd, Chesapeake, VA
The price is CA $193 per night from Jun 1 to Jun 2
CA $193
CA $224 total
includes taxes & fees
Jun 1 - Jun 2
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! (615 reviews)
"GOOD"

Reviewed on May 27, 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 CA $187 per night from Jun 15 to Jun 16
CA $187
CA $216 total
includes taxes & fees
Jun 15 - Jun 16
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! (1,002 reviews)
"Nice place clean, well taken care of."

Reviewed on May 26, 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.

Luxury Hotels in Chesapeake

Aloft Chesapeake

Aloft Chesapeake

3 out of 5
1454 Crossways Boulevard, Chesapeake, VA
The price is CA $172 per night from Jun 1 to Jun 2
CA $172
CA $199 total
includes taxes & fees
Jun 1 - Jun 2
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! (1,001 reviews)
"Very clean hotel with friendly staff. The pool could definitely use an update. But there was a cute little lounge area outside. Very convenient to shops."

Reviewed on May 26, 2025

Aloft 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 ...
7/10 Good! (1,001 reviews)
"."

Reviewed on May 8, 2025

Red Roof Inn Chesapeake Conference Center
Hyatt Place Chesapeake

Hyatt Place Chesapeake

3 out of 5
709 Eden Way N, Chesapeake, VA
The price is CA $187 per night from Jun 15 to Jun 16
CA $187
CA $216 total
includes taxes & fees
Jun 15 - Jun 16
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! (1,002 reviews)
"Nice place clean, well taken care of."

Reviewed on May 26, 2025

Hyatt Place Chesapeake
Save an average of 15% on thousands of hotels when you're signed in
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
The price is CA $128 per night from Jun 4 to Jun 5
CA $128
CA $149 total
includes taxes & fees
Jun 4 - Jun 5
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 ...
8.2/10 Very Good! (1,007 reviews)
"Nice comfortable stay"

Reviewed on May 26, 2025

Comfort Suites Chesapeake - Norfolk
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.

Family Friendly Hotels in Chesapeake

Hyatt Place Chesapeake

Hyatt Place Chesapeake

3 out of 5
709 Eden Way N, Chesapeake, VA
The price is CA $187 per night from Jun 15 to Jun 16
CA $187
CA $216 total
includes taxes & fees
Jun 15 - Jun 16
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! (1,002 reviews)
"Nice place clean, well taken care of."

Reviewed on May 26, 2025

Hyatt Place Chesapeake
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
The price is CA $128 per night from Jun 4 to Jun 5
CA $128
CA $149 total
includes taxes & fees
Jun 4 - Jun 5
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 ...
8.2/10 Very Good! (1,007 reviews)
"Nice comfortable stay"

Reviewed on May 26, 2025

Comfort Suites Chesapeake - Norfolk
SpringHill Suites by Marriott Chesapeake Greenbrier

SpringHill Suites by Marriott Chesapeake Greenbrier

3 out of 5
1446 Crossways Blvd, Chesapeake, VA
The price is CA $171 per night from Jun 22 to Jun 23
CA $171
CA $198 total
includes taxes & fees
Jun 22 - Jun 23
Stay at this 3-star business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the ...
8/10 Very Good! (1,000 reviews)
"Fantastic property, great rooms!"

Reviewed on May 26, 2025

SpringHill Suites by Marriott Chesapeake Greenbrier
Save an average of 15% on thousands of hotels when you're signed in
Aloft Chesapeake

Aloft Chesapeake

3 out of 5
1454 Crossways Boulevard, Chesapeake, VA
The price is CA $172 per night from Jun 1 to Jun 2
CA $172
CA $199 total
includes taxes & fees
Jun 1 - Jun 2
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! (1,001 reviews)
"Very clean hotel with friendly staff. The pool could definitely use an update. But there was a cute little lounge area outside. Very convenient to shops."

Reviewed on May 26, 2025

Aloft 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.

Best Chesapeake Flight and Hotel Packages

Chesapeake flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Sea Ranch Resort
John Yancey Oceanfront Inn
The Sanderling
Don't see what you're looking for?
See all available trips from Toronto to Chesapeake
View all trips

Need a car after flight to Chesapeake?

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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.