Cheap Flight Deals to Chesapeake VA from CA $42

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 $83 and CA $42 for one-way flights to Chesapeake for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSNorfolkJune 14 to June 17CA $83
MCONorfolkJuly 5 to July 8CA $178
ATLNorfolkJune 17 to June 24CA $296
DENNorfolkJune 9 to June 11CA $299
DALNorfolkAugust 14 to August 21CA $436
LAXNorfolkJune 10 to June 13CA $462
SANNorfolkJune 15 to June 20CA $763
SEANorfolkJune 13 to June 17CA $766
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
DENNorfolkJune 9 to June 11CA $299
BOSNorfolkJune 9 to June 18CA $427
DALNorfolkJune 8 to June 18CA $545
LAXNorfolkJune 9 to June 10CA $551
SEANorfolkJune 8 to June 16CA $819
*Prices include taxes and fees

Your guide to flights to Chesapeake, VA

Spirit Airlines, Delta, American Airlines 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 $83 and CA $819. 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 $83. 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 $162 per night from Jun. 2 to Jun. 3
CA $162
per night
Jun. 2 - Jun. 3
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 ...
8.2/10 Very Good! (1,002 reviews)
"Great"

Reviewed on 28 May 2024

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 $109 per night from Jun. 2 to Jun. 3
CA $109
per night
Jun. 2 - Jun. 3
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 (507 reviews)
"Difficult to find. Need marker on main road."

Reviewed on 5 May 2024

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 $104 per night from Jun. 9 to Jun. 10
CA $104
per night
Jun. 9 - Jun. 10
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 (740 reviews)
"Convenient location and staff was very helpful"

Reviewed on 27 May 2024

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
The price is CA $121 per night from Jun. 2 to Jun. 3
CA $121
per night
Jun. 2 - Jun. 3
Stay at this hotel in Chesapeake. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Greenbrier Mall and Waterside District are located ...
6.8/10 (1,000 reviews)
"I appreciated that they let me have my dog. The room smelled a bit strange before I came in though"

Reviewed on 12 May 2024

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 $215 per night from Jun. 17 to Jun. 18
CA $215
per night
Jun. 17 - Jun. 18
Stay at this 3-star business-friendly hotel in Chesapeake. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Greenbrier Mall and ...
7.8/10 Good! (569 reviews)
"I wish there were more restaurant options on this exit."

Reviewed on 31 May 2024

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 $195 per night from Jun. 9 to Jun. 10
CA $195
per night
Jun. 9 - Jun. 10
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! (1,001 reviews)
"Comfortable, clean, staff was excellent, location good for shopping and dining, would recommend to anyone."

Reviewed on 28 May 2024

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 $166 per night from Jun. 9 to Jun. 10
CA $166
per night
Jun. 9 - Jun. 10
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 ...
8/10 Very Good! (1,002 reviews)
"This is my first time staying with Aloft. Love the modernity, comfy room and bed, spacious bathroom, and very kind staff."

Reviewed on 28 May 2024

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 $121 per night from Jun. 2 to Jun. 3
CA $121
per night
Jun. 2 - Jun. 3
Stay at this hotel in Chesapeake. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Greenbrier Mall and Waterside District are located ...
6.8/10 (1,000 reviews)
"I appreciated that they let me have my dog. The room smelled a bit strange before I came in though"

Reviewed on 12 May 2024

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 $195 per night from Jun. 9 to Jun. 10
CA $195
per night
Jun. 9 - Jun. 10
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! (1,001 reviews)
"Comfortable, clean, staff was excellent, location good for shopping and dining, would recommend to anyone."

Reviewed on 28 May 2024

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 $162 per night from Jun. 2 to Jun. 3
CA $162
per night
Jun. 2 - Jun. 3
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 ...
8.2/10 Very Good! (1,002 reviews)
"Great"

Reviewed on 28 May 2024

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 $195 per night from Jun. 9 to Jun. 10
CA $195
per night
Jun. 9 - Jun. 10
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! (1,001 reviews)
"Comfortable, clean, staff was excellent, location good for shopping and dining, would recommend to anyone."

Reviewed on 28 May 2024

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 $162 per night from Jun. 2 to Jun. 3
CA $162
per night
Jun. 2 - Jun. 3
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 ...
8.2/10 Very Good! (1,002 reviews)
"Great"

Reviewed on 28 May 2024

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 $179 per night from Jun. 9 to Jun. 10
CA $179
per night
Jun. 9 - Jun. 10
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 ...
8.2/10 Very Good! (1,004 reviews)
"This is an older property but is a good value. The rooms are good-sized and comfortable. The staff was excellent, both friendly and professional. The complementary breakfast was also very well done. It is well worth the price if you can look past a few dents, dings, and stains."

Reviewed on 31 May 2024

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 $166 per night from Jun. 9 to Jun. 10
CA $166
per night
Jun. 9 - Jun. 10
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 ...
8/10 Very Good! (1,002 reviews)
"This is my first time staying with Aloft. Love the modernity, comfy room and bed, spacious bathroom, and very kind staff."

Reviewed on 28 May 2024

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
Sanderling Resort Residences
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?

Frequently asked questions

Which airlines fly to Chesapeake?
Chosen the datesfor your getaway toChesapeake?With 7airline companies servicing this city,you’re bound to find a flightthat fits perfectly with your travel plans.Here are a few ofthe leading companies:

  • American Airlines
  • Delta Air Lines
  • United Airlines

What airport is best to fly into Chesapeake?
With two airports, you’ve got options when flying into Chesapeake. Think about where you’ll be basing yourself and spending a lot of your time, as this may help you decide on which flights you select. Norfolk Intl. Airport is 16 kilometers from all the action downtown, while Newport News - Williamsburg Intl. Airport is roughly 48 kilometers away.
Where to stay in Chesapeake
Every unforgettable journey starts with a single step — as well as a comfortable place to lay your head! Book your Chesapeake accommodations through Travelocity and you’ll have 188 options to choose from.Craving a taste of the good life on your trip? Book a luxurious room with all the fancy extras at the The Founders Inn and Spa, Tapestry Collection by Hilton. If you’d rather be more economical with your accommodations, choose a budget option like the Econo Lodge Chesapeake Route 13 and I-464.
Places to visit in Chesapeake
Want some sightseeing hints? Don’t leave this bustling city until you’ve visited Children’s Museum of Virginia, and Nauticus National Maritime Center.0 Seeking some more ideas? 0 But there’s more. 0
How to get through airport security fast when traveling to Chesapeake
These practical tips and hints about airport security procedures will save you lots of time and energy on your journey to Chesapeake:

  • Make sure your boarding pass and travel ID are not difficult to reach. You’ll be required to produce them straightaway.
  • Wallets, USB sticks and keys should be put in a bin for X-raying. If you pass through the body scanner with these items, you’ll be asked to turn back and remove them.
  • Make sure your laptop and electronic devices are within reach. These items need to be sent through the X-ray machine in separate tubs.
  • Toothpaste, lip balm and other toiletry items in liquid, gel or cream form need to be stored in containers smaller than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock plastic bag.
  • The airport security will likely ask you to remove your shoes prior to entering the body scanner. Wear a pair that come off easily. There’s nothing more tiresome than having to do up your laces over and over again.
  • Stash any multi-tools or other dangerous items inside your checked luggage. Security won’t permit these in carry-on baggage.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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.