Chesapeake Vacations

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Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Greenbrier Mall

Greenbrier East

1 out of top 10 points of interest in this area
4/5(438 area reviews)

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.

Find hotels in Greenbrier East

Find the Best Chesapeake Vacation Packages

Chesapeake Hotel Deals

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AED 265 per night from Nov 13 to Nov 14
AED 265
AED 313 total
13 Nov - 14 Nov
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Extremely helpful at check-in. Thank you!

Reviewed on 9 November 2025

Comfort Suites Chesapeake - Norfolk
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AED 291 per night from Nov 23 to Nov 24
AED 291
AED 342 total
23 Nov - 24 Nov
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Great

Reviewed on 6 November 2025

Wingate by Wyndham Chesapeake
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AED 276 per night from Nov 16 to Nov 17
AED 276
AED 324 total
16 Nov - 17 Nov
includes taxes & fees
6.8/10 (1,000 reviews)
Amazing staff. Clean rooms. But other guest were smoking weed and you could smell it in our room all night.

Reviewed on 26 October 2025

Red Roof Inn Chesapeake Conference Center
See all 3,385 properties in 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.

Discover the most popular places to visit in Chesapeake

Greenbrier Mall

Greenbrier Mall

You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.

Greenbrier Mall
Chesapeake Square Mall

Chesapeake Square Mall

You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Chesapeake Square Mall
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theater scene.

Chesapeake Conference Center

Frequently asked questions

How do I find cheap flights to Chesapeake that have flexible change policies?
We know that travel schedules can change from one minute to the next, so reserving a flexible ticket with Expedia is always a smart move. Simply mark the "No change fee" box directly under the "Flexible change policies" filter. Your affordable, flexible flight to Chesapeake is just a few clicks away.
Which airlines fly to Chesapeake?
Whether you'd like to sit in first class or save in economy, these top carriers will fly you comfortably to or near Chesapeake:

  • American Airlines - 836 flights to or near Chesapeake each month, including 715 flights to Norfolk Intl. Airport (ORF) per month.
  • United Airlines - 355 flights to or near Chesapeake each month, including 355 flights to Norfolk Intl. Airport (ORF) per month.

How can I find cheap tickets to Chesapeake?
An useful strategy for nabbing cheap tickets is to be flexible with your travel dates. Start by searching for your flight to Chesapeake, then click on the "flexible dates" link to see prices for nearby days. Another tip? Book well ahead. To give you an idea of fares, was the lowest price for a flight to Chesapeake in the last seven days.
How much is a flight to Chesapeake?
In the last seven days, round-trip tickets to Chesapeake sold for as little as and peaked at . For one-way trips leaving (), the lowest amount paid during this same period was just .
What are the most popular airports to fly into in Chesapeake?
Depending on which carrier you travel with and departure city, one of these main airports will be your entry point to Chesapeake:

  • Norfolk Intl. Airport (ORF) - 1,824 flights per month.
  • Newport News - Williamsburg Intl. Airport (PHF) - 121 flights per month.

When is the cheapest time to fly to Chesapeake?
If you're not set on what date you jet off to Chesapeake, try to leave early on in the week. The most economical day to take off is generally Tuesday, followed closely by Monday. Saturday is typically the priciest day, with many vacationers preferring to take off on the weekend.
How much is a plane ticket to Chesapeake?
Plane fares ranged anywhere from to in the last seven days. When you're ready to book, we'll help you grab a great deal to Chesapeake.
What months are the cheapest to book a flight to Chesapeake?
Book your ticket in February for amazing flight deals to Chesapeake. The month of December is known as the most expensive time to buy a seat.
How long is a flight to Chesapeake?
That depends on where you fly from. These leading domestic routes and their average flight times will give you a better idea of how long it'll take to get to Chesapeake:

  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Norfolk Intl. Airport (ORF) - 1 hour and 17 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Norfolk Intl. Airport (ORF) - 1 hour and 31 minutes
  • Washington, DC (IAD-Washington Dulles Intl.) to Norfolk Intl. Airport (ORF) - 1 hour and 4 minutes