Chesterfield Trips (flight + hotel)

Photo by Michelle E

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination on Expedia. But how much your vacation to Chesterfield costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chesterfield?
December, January and February are great times to search for cheap Chesterfield vacation packages. Traveling in less busy periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Chesterfield?
With about 2 days, you'll have plenty of time to enjoy popular neighborhoods such as Clarkson Valley and Winchester during your Chesterfield vacation. Be sure to also add Myseum and The Factory to your sightseeing itinerary. In the mood for more adventures? Consider exploring outside of Chesterfield on day trips and tours.
Is it worth booking a vacation package to Chesterfield?
Chesterfield has all the ingredients you need for an amazing break --- golfing, nature and shopping are just the start. Whether you'd like to check out sights like The Factory and Chesterfield Sports Fusion, or venture off the beaten track, you'll have plenty to do on your Chesterfield vacation.
How to find the best Chesterfield package deals?
Begin your search for a Chesterfield package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesterfield package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesterfield adventure underway.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a customized Chesterfield vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Chesterfield?
If you've got your Chesterfield travel dates finalized, book as early as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Chesterfield?

  1. Choose your dates: What you plan to do in Chesterfield and your favorite season can help you decide when to get away.
  2. Set a budget: Consider expenses like transportation, flights and meals when calculating how much to set aside for your trip to Chesterfield. Then, choose a hotel that works with your budget, whether that's an affordable option or a high-end retreat.
  3. Decide your trip length: Think about how long you'd like to spend exploring Chesterfield. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the right Chesterfield vacation package for you.

Popular places to visit

St. Louis Zoo featuring a park, a bridge and a lake or waterhole

St. Louis Zoo

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo
Gateway Arch featuring central business district, modern architecture and skyline

Gateway Arch

Visit the Museum of Westward Expansion, then ascend to the top of the tallest man-made monument in the US for breathtaking views of St. Louis.

Gateway Arch

America's Center Convention Complex

Learn about the events happening at America's Center Convention Complex during your trip to St. Louis. Experience the area's acclaimed theater scene and great live music.

America's Center Convention Complex

What to do in Chesterfield

St. Louis Arch Walking Tour and Entrance Ticket

St. Louis Arch Walking Tour and Entrance Ticket

P2,808
per adult
St. Louis Arch Walking Tour and Entrance Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis: Gateway Ghouls and Hauntings Walking Tour

P1,348
per adult
St. Louis: Gateway Ghouls and Hauntings Walking Tour
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

P1,517
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Chesterfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.