Cheap Flight Deals to Chesapeake Bay  from CA $185

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

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 Bay?

The cheapest prices found with in the last 7 days for return flights were CA $99 and CA $185 for one-way flights to Chesapeake Bay for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Aug. 29 - Wed, Sep. 3
YTZ
Billy Bishop Toronto City
DCA
Ronald Reagan Washington National
CA $309 Roundtrip, found 5 days ago
CA $309
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Aug. 29 from Billy Bishop Toronto City to Ronald Reagan Washington National, returning Wed, Sep. 3, priced at CA $309 found 5 days ago
OriginDestinationTravel datesFlights from*
ATLBaltimoreAugust 16 to August 18CA $99
LAXBaltimoreAugust 16 to August 23CA $111
MCOBaltimoreSeptember 5 to September 7CA $174
MCOWashingtonSeptember 24 to September 28CA $181
BOSRichmondOctober 27 to November 13CA $202
BOSWashingtonSeptember 4 to September 10CA $206
TPAWashingtonSeptember 10 to September 14CA $242
ATLNorfolkJuly 31 to August 17CA $289
SFOWashingtonAugust 30 to September 6CA $354
DFWChantillyAugust 3 to August 16CA $371
BOSChantillyJuly 30 to August 4CA $400
SFOBaltimoreAugust 14 to August 19CA $499
ATLWashingtonAugust 7 to August 10CA $994
FCOWashingtonSeptember 14 to September 19CA $1,270
MIAWashingtonAugust 20 to November 3CA $7,655
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLBaltimoreJuly 26 to July 27CA $263
BOSBaltimoreJuly 27 to August 3CA $306
MIABaltimoreJuly 25 to July 27CA $311
LAXBaltimoreJuly 26 to July 28CA $653
LAXWashingtonJuly 26 to July 28CA $1,016
SFOChantillyJuly 25 to August 5CA $1,100
LAXChantillyJuly 26 to July 28CA $1,130
DENBaltimoreJuly 25 to July 27CA $1,715
*Prices include taxes and fees

Your guide to flights to Chesapeake Bay,

Air Canada fly to Chesapeake Bay, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chesapeake Bay currently costs between CA $99 and CA $7,655. Prices vary, but for the best fares, travel in August 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 $99. 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 August 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! (1,156 reviews)
"Appreciate the sea staying up so late arrival 1230am and departure 509am"

Reviewed on Jul. 20, 2025

Get rates
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
The price is CA $126 per night from Aug 1 to Aug 2
CA $126
CA $146 total
Aug 1 - Aug 2
includes taxes & fees
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! (1,651 reviews)
"Well designed room layout with thoughtful consideration to the practical needs of its guests. Good location within walking distances of major attractions. Would like to come back to stay next time in DC."

Reviewed on Jul. 21, 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 (1,001 reviews)
"Unique hotel style and good location."

Reviewed on Jul. 14, 2025

Get rates
The Baron Hotel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Inns Of Virginia - Arlington

Inns Of Virginia - Arlington

2 out of 5
3335 Langston Blvd, Arlington, VA
The price is CA $109 per night from Jul 24 to Jul 25
CA $109
CA $124 total
Jul 24 - Jul 25
includes taxes & fees
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 ...
6.8/10 (1,007 reviews)
"Everything"

Reviewed on Jul. 20, 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
The price is CA $154 per night from Jul 25 to Jul 26
CA $154
CA $176 total
Jul 25 - Jul 26
includes taxes & fees
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! (1,007 reviews)
"DCA has great options for layovets and easy access to 5he metro / trains from the airport."

Reviewed on Jul. 21, 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
The price is CA $149 per night from Aug 1 to Aug 2
CA $149
CA $170 total
Aug 1 - Aug 2
includes taxes & fees
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 ...
8.2/10 Very Good! (1,144 reviews)
"The staff was very friendly and accommodating"

Reviewed on Jul. 20, 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! (1,156 reviews)
"Appreciate the sea staying up so late arrival 1230am and departure 509am"

Reviewed on Jul. 20, 2025

Get rates
Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Hilton Arlington National Landing

Hilton Arlington National Landing

4 out of 5
2399 Richmond Hwy, Arlington, VA
The price is CA $161 per night from Aug 1 to Aug 2
CA $161
CA $184 total
Aug 1 - Aug 2
includes taxes & fees
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 ...
8.8/10 Excellent! (551 reviews)
"I was very impressed with how genuinely nice the staff were- from the front desk staff engaging in conversation, to the hotel maintenance staff being courteous as we got on the elevator. They were all very customer service oriented and while it was just a little thing, it went a long way with initial ..."

Reviewed on Jul. 20, 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

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

The Watergate Hotel

5 out of 5
2650 Virginia Ave NW, Washington, DC
The price is CA $339 per night from Aug 1 to Aug 2
CA $339
CA $451 total
Aug 1 - Aug 2
includes taxes & fees
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 ...
8.8/10 Excellent! (1,011 reviews)
"Great stay!"

Reviewed on Jul. 18, 2025

The Watergate Hotel
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
806 15th Street NW, Washington, DC
The price is CA $280 per night from Jul 26 to Jul 27
CA $280
CA $372 total
Jul 26 - Jul 27
includes taxes & fees
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! (1,008 reviews)
"Great location...central to shopping, dining, culture! Room was VERY spacious and clean. The valet was not as attentive for the daily charge. Waited for car service over 30 minutes each time."

Reviewed on Jul. 22, 2025

Sofitel Washington DC Lafayette Square
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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! (956 reviews)
"A lovely quiet hotel in the middle of the city. Wonderful staff and hospitality…"

Reviewed on Jul. 6, 2025

Get rates
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
The price is CA $114 per night from Aug 12 to Aug 13
CA $114
CA $168 total
Aug 12 - Aug 13
includes taxes & fees
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 ...
9/10 Wonderful! (2,841 reviews)
"Very convenient to local attractions"

Reviewed on Jul. 19, 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
The price is CA $172 per night from Aug 13 to Aug 14
CA $172
CA $200 total
Aug 13 - Aug 14
includes taxes & fees
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! (1,898 reviews)
"The staff were very amazing and caring. The experience of our stay at the hotel was fantastic."

Reviewed on Jul. 22, 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
The price is CA $138 per night from Aug 4 to Aug 5
CA $138
CA $195 total
Aug 4 - Aug 5
includes taxes & fees
Stay at this 3-star golf resort in Williamsburg. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,003 reviews)
"Nice updates. Every thing was very nice. Only complaint was the ratchet people who came two days before we left making noise til 5:00 am."

Reviewed on Jul. 21, 2025

Hilton Vacation Club Greensprings Williamsburg
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
The price is CA $189 per night from Jul 27 to Jul 28
CA $189
CA $219 total
Jul 27 - Jul 28
includes taxes & fees
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! (2,842 reviews)
"This was a great location. Walking distance to most major tourist sites."

Reviewed on Jul. 21, 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.
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Warner Hall

Warner Hall

3 out of 5
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Don't see what you're looking for?
See all available trips from Toronto to Chesapeake Bay
View all trips

Need a car after flight to Chesapeake Bay?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

How much is the cheapest flight to Chesapeake Bay?
Based on prices found over the last seven days, a roundtrip flight to Chesapeake Bay was as low as CA $99. If you're flexible with your dates, it's easier to snap up a great bargain. This price was available on Travelocity for flights to Chesapeake Bay departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Chesapeake Bay?
Make sure you leave August free in your calendar, because it's the most affordable month to jet to Chesapeake Bay. That's according to Travelocity's direct flight demand between January and December last year. With the cash you save, you can upgrade your hotel booking, go to a fancy restaurant or whatever makes you happy.
How can I check my flight status to Chesapeake Bay?
Get updates about flight delays, gate number changes and more with Trips. Travelocity's handy portal is located at the top right of our homepage and is the place to view and manage your bookings. Create an account easily and quickly and you're ready to go. The Travelocity app also lets you see the details of your flight to Chesapeake Bay while you're out and about — and even while you're offline. The app has your booking needs sorted. Whether you want to arrange transportation from your airport or share itineraries with any members of your family flying with you, you can do it through the app.
How do I find the best deals on flights to Chesapeake Bay?
Nab an incredible deal with Travelocity — our "Flexible dates" feature makes it so much easier. Enter your desired dates, then tap or click on the flexible dates box above your results to compare prices with the surrounding days. CA $99 was the cheapest price for a return flight to Chesapeake Bay in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Chesapeake Bay with Travelocity?
From cheap flights to Chesapeake Bay to activities, rental cars and more, Travelocity has got you covered for amazing adventures. With everything you need in one convenient place, you can enjoy more time thinking about the wonderful things you'll be discovering in Chesapeake Bay and less time on the nitty-gritty of travel planning. Plus with our Price Match Guarantee and online chat support, we do our best to make your next break a hassle-free one.
How much is a flight to Chesapeake Bay on average?
Based on prices found over the last seven days, roundtrip flights to Chesapeake Bay cost between CA $99 and CA $7,655. When you're ready to take off, Travelocity will help you find a fare that'll work with your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

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.