Cheap Flight Deals to Chesapeake VA from CA $157

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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 $132 and CA $157 for one-way flights to Chesapeake for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSNorfolkJuly 13 to July 21CA $263
*Prices include taxes and fees

Your guide to flights to Chesapeake, VA

Spirit Airlines, 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 $132 and CA $414. Prices vary, but for the best fares, travel in June 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 $132. 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 $111 per night from Apr. 27 to Apr. 28
CA $111
CA $129 total
includes taxes & fees
Apr 27 - Apr 28
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! (1,002 reviews)
"Good place. Clean and convenient. Excellent breakfast."

Reviewed on Apr. 14, 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 $100 per night from Apr. 17 to Apr. 18
CA $100
CA $117 total
includes taxes & fees
Apr 17 - Apr 18
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 ...
6/10 (582 reviews)
Pay for what you get.
"The elevator was being serviced… that was the only issue."

Reviewed on Apr. 14, 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 $95 per night from Apr. 20 to Apr. 21
CA $95
CA $119 total
includes taxes & fees
Apr 20 - Apr 21
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 (856 reviews)
"Our stay was comfortable and pleasant. The area was safe. It is a good choice for a reasonable hotel to stay in the area we needed."

Reviewed on Mar. 27, 2025

Comfort Inn & Suites Chesapeake - Portsmouth
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Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
The price is CA $104 per night from Apr. 24 to Apr. 25
CA $104
CA $121 total
includes taxes & fees
Apr 24 - Apr 25
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! (1,002 reviews)
"The staff here is very knowledgeable and nice."

Reviewed on Mar. 31, 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 $156 per night from Apr. 19 to Apr. 20
CA $156
CA $181 total
includes taxes & fees
Apr 19 - Apr 20
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! (603 reviews)
"The room was very spacious."

Reviewed on Apr. 7, 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 $133 per night from Apr. 27 to Apr. 28
CA $133
CA $154 total
includes taxes & fees
Apr 27 - Apr 28
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! (1,003 reviews)
"Clean and comfortable!"

Reviewed on Apr. 8, 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 $137 per night from Apr. 20 to Apr. 21
CA $137
CA $159 total
includes taxes & fees
Apr 20 - Apr 21
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)
"Great staff, comfy bed, amazing shower"

Reviewed on Apr. 5, 2025

Aloft Chesapeake
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
The price is CA $104 per night from Apr. 24 to Apr. 25
CA $104
CA $121 total
includes taxes & fees
Apr 24 - Apr 25
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! (1,002 reviews)
"The staff here is very knowledgeable and nice."

Reviewed on Mar. 31, 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 $133 per night from Apr. 27 to Apr. 28
CA $133
CA $154 total
includes taxes & fees
Apr 27 - Apr 28
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! (1,003 reviews)
"Clean and comfortable!"

Reviewed on Apr. 8, 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 $111 per night from Apr. 27 to Apr. 28
CA $111
CA $129 total
includes taxes & fees
Apr 27 - Apr 28
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! (1,002 reviews)
"Good place. Clean and convenient. Excellent breakfast."

Reviewed on Apr. 14, 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 $133 per night from Apr. 27 to Apr. 28
CA $133
CA $154 total
includes taxes & fees
Apr 27 - Apr 28
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! (1,003 reviews)
"Clean and comfortable!"

Reviewed on Apr. 8, 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 $111 per night from Apr. 27 to Apr. 28
CA $111
CA $129 total
includes taxes & fees
Apr 27 - Apr 28
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! (1,002 reviews)
"Good place. Clean and convenient. Excellent breakfast."

Reviewed on Apr. 14, 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 $137 per night from Apr. 20 to Apr. 21
CA $137
CA $159 total
includes taxes & fees
Apr 20 - Apr 21
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! (1,003 reviews)
"The staff were very friendly and helpful. The room was clean as well as the bathroom. I have stayed here before and will stay again when in the area."

Reviewed on Apr. 11, 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 $137 per night from Apr. 20 to Apr. 21
CA $137
CA $159 total
includes taxes & fees
Apr 20 - Apr 21
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)
"Great staff, comfy bed, amazing shower"

Reviewed on Apr. 5, 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.
Best Western Plus Newport News Inn & Suites
Hampton Inn & Suites Newport News (Oyster Point)
Comfort Inn & Suites Hampton near Coliseum
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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.