Chesapeake Vacations

Book a Hotel + Flight together to unlock savings

Photo by Kaylee Spinhirn

  • Plan, book, travel with confidence

  • Better together

    Save up to AED 148 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Chesapeake

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

Greenbrier West

3 out of top 10 points of interest in this area
3.5/5(49 area reviews)

If you're spending some time in Greenbrier West, Bowlero Chesapeake and Chesapeake Arboretum are top sights worth seeing.

Find hotels in Greenbrier West

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 247 per night from Dec 30 to Dec 31
AED 247
AED 291 total
30 Dec - 31 Dec
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Staff was very helpful and friendly throughout our stay. The floor and area of my room was peaceful and quiet. The room was very clean and comfortable.

Reviewed on 27 December 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 Jan 1 to Jan 2
AED 291
AED 342 total
1 Jan - 2 January 2026
includes taxes & fees
7.8/10 Good! (1,008 reviews)
I wasn’t as impressed with this stay. Could not fill the tub in 1st room. 2nd room had a much smaller tv. Both rooms only had 2 usb chargers. I can only give a good rating. Don’t think I would stay again

Reviewed on 19 December 2025

Wingate by Wyndham Chesapeake
Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive Chesapeake VA
Fully refundable
The price is AED 290 per night from Jan 1 to Jan 2
AED 290
AED 341 total
1 Jan - 2 January 2026
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Great thanks

Reviewed on 27 December 2025

Holiday Inn Express Chesapeake - Norfolk by IHG
See all 3,395 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 acclaimed theater scene and great live music.

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