Chesterfield Vacation Packages 2026 from $495

Chesterfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Larkspur Landing Extended Stay Suites St. Louis Riverport - Airport West

Riverport

$495

per person

Nov 13 - Nov 18

found 11 hours ago

Roundtrip flight included

Los Angeles (LAX) to St. Louis (STL)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Residence Inn by Marriott St Louis Downtown

Midtown

$588

per person

Nov 13 - Nov 18

found 11 hours ago

Roundtrip flight included

Los Angeles (LAX) to St. Louis (STL)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a grocery/convenience store are also offered.

Ameristar Casino Resort and Spa

$846

per person

Nov 13 - Nov 18

found 11 hours ago

Roundtrip flight included

Los Angeles (LAX) to St. Louis (STL)

This luxury hotel features a casino, a full-service spa, and 6 restaurants. Enjoy the 2 hot tubs and outdoor pool, and unwind with a drink at the poolside bar.

Crowne Plaza St. Louis Airport by IHG

$577

per person

Nov 13 - Nov 18

found 11 hours ago

Roundtrip flight included

Los Angeles (LAX) to St. Louis (STL)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like a free area shuttle.

Hollywood Casino & Hotel St. Louis

Riverport

$596

per person

Nov 13 - Nov 18

found 11 hours ago

Roundtrip flight included

Los Angeles (LAX) to St. Louis (STL)

A casino, 7 restaurants, and a 24-hour gym are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, express check-out, and free airport shuttle. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Top Chesterfield hotels deals

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$132 total

Sep 29 - Sep 30

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a garden, and express check-out are also on offer.

Pool

Breakfast included

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$151 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

11 Arnage Boulevard Chesterfield MO

Free Cancellation

$114 nightly

$133 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Clayton Plaza Hotel & Extended Stay

7750 Carondelet Avenue St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$108 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the sauna and free full breakfast each morning.

Pool

Breakfast included

Hyatt Regency St. Louis at The Arch

315 Chestnut St St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$158 total

Oct 2 - Oct 3

Total with taxes and fees

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

Pet friendly

Free WiFi

Pear Tree Inn St. Louis Airport

10810 Pear Tree Ln St. Ann MO

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$106 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

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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.

Stay near popular Chesterfield attractions

The Factory

8.8/10 (47 reviews)

You can make plans for a show at The Factory on your trip to Chesterfield. Check out the shops and top-notch restaurants in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Chesterfield?

Travelocity has flight and hotel vacation packages from an incredible $495. With such great deals, you'll be exploring all of Chesterfield before you know it.

How long should my Chesterfield vacation be?

There are no rules when it comes to how long you should spend in Chesterfield, but most people opt to stay for around 2 nights. Got some flexibility with your departure date? Consider treating yourself to a couple of extra nights. That way, you'll have loads of time to check out the surrounding areas as well.

Where can I get the best vacation package deals for Chesterfield?

There's no need to look any further than Travelocity. With no less than 400 airlines and 1,000,000 properties around the world, it's a breeze to put together a Chesterfield package deal that suits your travel style.

Why should I book my Chesterfield vacation package with Travelocity?

You'll not only enjoy huge savings, but you'll also have access to our round-the-clock support, quality service and a Price Match Guarantee. Wander across the world, uncover hidden gems and make unforgettable memories — we'll take care of the important details.

Will I save money on my Chesterfield car rental if I combine it with my hotel or flight?

Bundling your bookings into a Chesterfield vacation package will save you some serious money. Book a car and flight; a hotel, flight and car; or a hotel and car. There's no better way to explore the greater Chesterfield area than with your own rental car. You can also add experiences and tours to your Travelocity package.

Which airport is best for Chesterfield?

That would be Lambert-St. Louis Intl. Airport (STL), located 12 mi northeast of central Chesterfield.

What is there to do in Chesterfield?

While hopping off the tourist trail is no doubt rewarding, you shouldn't ignore the well-known sights that make a place famous. St. Louis Premium Outlets and Chesterfield Sports Fusion are just two of them in Chesterfield.

Where should I stay when visiting Chesterfield?

Many people spend their nights at the Drury Plaza Hotel St. Louis Chesterfield. It's sure to be a good base for your Chesterfield vacation.