Cheap Flight Deals to Chesapeake Bay  from CA $162

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How to find cheap flights to Chesapeake Bay?

The cheapest prices found with in the last 7 days for return flights were CA $88 and CA $162 for one-way flights to Chesapeake Bay for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSBaltimoreSeptember 4 to September 10CA $88
ATLBaltimoreSeptember 6 to September 13CA $98
MCOBaltimoreJuly 1 to July 5CA $131
MCOWashingtonSeptember 4 to September 10CA $157
MIABaltimoreJune 25 to June 29CA $181
LAXBaltimoreJuly 10 to July 14CA $207
ATLChantillyAugust 4 to August 6CA $219
ATLRichmondJune 26 to June 30CA $226
ATLWashingtonAugust 4 to August 7CA $228
BOSNorfolkJune 25 to June 30CA $239
DENWashingtonAugust 21 to August 27CA $324
LAXRichmondSeptember 5 to September 7CA $332
LAXChantillyJuly 18 to July 21CA $401
DENChantillyJuly 1 to July 5CA $569
BOSChantillyJune 22 to June 24CA $858
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
BOSBaltimoreJune 20 to June 22CA $290
DFWWashingtonJune 21 to June 24CA $372
BOSNorfolkJune 20 to June 30CA $394
MIABaltimoreJune 20 to June 23CA $405
DFWChantillyJune 21 to June 24CA $407
BOSChantillyJune 20 to June 24CA $468
BOSWashingtonJune 22 to June 27CA $655
FCOChantillyJune 22 to July 7CA $802
SFOChantillyJune 20 to June 23CA $917
*Prices include taxes and fees

Your guide to flights to Chesapeake Bay,

Porter Airlines, WestJet, Air Canada fly to Chesapeake Bay, 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 Bay currently costs between CA $88 and CA $917. Prices vary, but for the best fares, travel in July when prices are at their lowest.  

Top tips for finding cheap flights to Chesapeake Bay  

The cheapest flight for a round trip to Chesapeake Bay is currently CA $88. When you search for flights to Chesapeake Bay, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chesapeake Bay for nearby days.  The cheapest month to travel to Chesapeake Bay is July 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 Bay 

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 Bay with Travelocity 

We have top deals on plane tickets even for last minute flights to Chesapeake Bay, 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 Bay for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Chesapeake Bay

Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport

Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport

2.5 out of 5
827 Elkridge Landing Road, Linthicum Heights, MD
Book a stay at this business-friendly hotel in Linthicum Heights. Enjoy free WiFi, free parking, and a free airport shuttle. Our guests praise the helpful staff ...
7.2/10 Good! (1,114 reviews)
"Easy. Shuttle was perfect"

Reviewed on Jun. 9, 2025

Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport
Motto by Hilton Washington DC City Center

Motto by Hilton Washington DC City Center

3.5 out of 5
627 H Street NW, Washington, DC
Stay at this 3.5-star hotel in Washington. Enjoy free WiFi, 3 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our ...
8.8/10 Excellent! (1,628 reviews)
"Everything was perfect."

Reviewed on Jun. 12, 2025

Motto by Hilton Washington DC City Center
The Baron Hotel

The Baron Hotel

3 out of 5
1523 22nd Street NW, Washington, DC
Stay at this 3-star hotel in Washington. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms ...
6.8/10 (1,002 reviews)
"Staff was helpful. They were having a show downstairs....everyone was very nice and mature towards my wife and kids even though there was a planned comedy show going on in the process of us checking in(because we checked in later at night)...We enjoyed our stay..."

Reviewed on Jun. 13, 2025

The Baron Hotel
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Inns Of Virginia - Arlington

Inns Of Virginia - Arlington

2 out of 5
3335 Langston Blvd, Arlington, VA
Book a stay at this business-friendly hotel in Arlington. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
6.6/10 (1,002 reviews)
"the neighborhood of this hotel is great and free parking lot is a plus. the inside of hotel is outdated but the room and bathroom are very clean which is not a problem."

Reviewed on Jun. 12, 2025

Inns Of Virginia - Arlington
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 Bay hotel with Airport Shuttles

The Westin Crystal City Reagan National Airport

The Westin Crystal City Reagan National Airport

4 out of 5
1800 Richmond Highway, Arlington, VA
Book a stay at this business-friendly hotel in Arlington. Enjoy a free airport shuttle, a 24-hour health club, and WiFi (surcharge). Our guests praise the helpful ...
8.6/10 Excellent! (1,002 reviews)
"Parking was expensive. Only down side"

Reviewed on Jun. 10, 2025

The Westin Crystal City Reagan National Airport
DoubleTree by Hilton Washington DC - Crystal City

DoubleTree by Hilton Washington DC - Crystal City

4 out of 5
300 Army Navy Dr, Arlington, VA
Stay at this 4-star business-friendly hotel in Arlington. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (1,094 reviews)
"Hotel was fantastic. Room was good however the shower/bathtub in room 1107 sounded like a bad foghorn but when you turned on the shower it went away. Overall great experience there!"

Reviewed on Jun. 12, 2025

DoubleTree by Hilton Washington DC - Crystal City
Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport

Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport

2.5 out of 5
827 Elkridge Landing Road, Linthicum Heights, MD
Book a stay at this business-friendly hotel in Linthicum Heights. Enjoy free WiFi, free parking, and a free airport shuttle. Our guests praise the helpful staff ...
7.2/10 Good! (1,114 reviews)
"Easy. Shuttle was perfect"

Reviewed on Jun. 9, 2025

Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport
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Hilton Arlington National Landing

Hilton Arlington National Landing

4 out of 5
2399 Richmond Hwy, Arlington, VA
Stay at this 4-star hotel in Arlington. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (497 reviews)
"It was a very good restful one-night stay."

Reviewed on Jun. 12, 2025

Hilton Arlington National Landing
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 Bay

The Fairfax at Embassy Row, Washington, D.C.

The Fairfax at Embassy Row, Washington, D.C.

3.5 out of 5
2100 Massachusetts Avenue NW, Washington, DC
Stay at this 3.5-star luxury hotel in Washington. Enjoy free parking, breakfast (surcharge), and a health club. Popular attractions White House and National ...
"It was pretty nice. Me and my husband went around 4 hours early and we couldn’t checkin but they took our luggage so we could walk around. It was close to restaurants so that makes everything easy for us. Good location. I would definitely come back."

Reviewed on May 24, 2020

The Fairfax at Embassy Row, Washington, D.C.
The Watergate Hotel

The Watergate Hotel

5 out of 5
2650 Virginia Ave NW, Washington, DC
Stay at this 5-star luxury hotel in Washington. Enjoy free WiFi, a full-service spa, and 3 bars/lounges. Our guests praise the bar and the helpful staff in our ...
8.6/10 Excellent! (1,005 reviews)
"The hotel lobby, restaurant, bar, and fitness were all excellent. The staff was friendly and helpful. The bathrooms with the marble everywhere and large double sink vanities were beautiful. Room was modern and clean. Bed was extremely comfortable."

Reviewed on Jun. 12, 2025

The Watergate Hotel
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
806 15th Street NW, Washington, DC
Stay at this 5-star luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,001 reviews)
"Perfect location Parking was easy Highly recommend"

Reviewed on Jun. 13, 2025

Sofitel Washington DC Lafayette Square
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The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
1200 16th St NW, Washington, DC
Stay at this 5-star luxury hotel in Washington. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
9.6/10 Exceptional! (943 reviews)
"Great service."

Reviewed on Jun. 11, 2025

The Jefferson, Washington, DC
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 Bay

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
Stay at this 3.5-star golf resort in Williamsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in ...
8.8/10 Excellent! (2,768 reviews)
"Updates of daily activities , lots of things to do, beautiful grounds."

Reviewed on Jun. 14, 2025

Hilton Vacation Club The Historic Powhatan Williamsburg
Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
900 10th St NW, Washington, DC
Stay at this 3.5-star business-friendly hotel in Washington. Enjoy free breakfast, a 24-hour fitness center, and WiFi (surcharge). Our guests praise the breakfast ...
9/10 Wonderful! (1,843 reviews)
"The room was very spacious and clean."

Reviewed on Jun. 13, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center
Hilton Vacation Club Greensprings Williamsburg

Hilton Vacation Club Greensprings Williamsburg

3 out of 5
3500 Ludwell Pkwy, Williamsburg, VA
Stay at this 3-star golf hotel in Williamsburg. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,003 reviews)
"Spacious! Amazing price! All the comforts of home. A great find! Quiet and private."

Reviewed on Jun. 12, 2025

Hilton Vacation Club Greensprings Williamsburg
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Holiday Inn Washington Capitol - Natl Mall by IHG

Holiday Inn Washington Capitol - Natl Mall by IHG

3 out of 5
550 C St SW, Washington, DC
Stay at this 3-star business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the breakfast and the pool ...
8.4/10 Very Good! (2,767 reviews)
Very close to Air and space museum
"It was very close to the air and space museum. It was warmer on our trip so what doesn’t seem like a long walk turned out to be a long walk. When we checked in we some friendly and fun people. When I went to the desk the next day I didn’t get the same fun people. She was doing her job and I respect ..."

Reviewed on Jun. 11, 2025

Holiday Inn Washington Capitol - Natl Mall by IHG
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 Bay Flight and Hotel Packages

Chesapeake Bay flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Patriots Inn
The Colonies at Williamsburg
Williamsburg Inn, an official Colonial Williamsburg Hotel
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Plane Tickets To Chesapeake Bay

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chesapeake Bay. Browse through our inventory to explore a wide range of cheap flights to Chesapeake Bay to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chesapeake Bay as you anxiously await to exit the plane and explore what Chesapeake Bay has to offer. Considering all the amazing local food and culture in Chesapeake Bay, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chesapeake Bay to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chesapeake Bay without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chesapeake Bay with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chesapeake Bay today!

*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.