Chesterfield Vacation Packages 2025/2026 from $274

Chesterfield flight + hotel vacation packages

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

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

$274

per person

Nov 13 - Nov 16

found 8 hours ago

Roundtrip flight included

Dallas (DFW) to St. Louis (STL)

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.

The Wildwood Hotel

Save 100% on your flight

$546

per person

Nov 6 - Nov 9

found 17 hours ago

Roundtrip flight included

Boston (BOS) to St. Louis (STL)

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. Enjoy the hot tub and free perks like continental breakfast and free self parking.

The Principal Hotel

$350

per person

Nov 7 - Nov 10

found 9 hours ago

Roundtrip flight included

Dallas (DFW) to St. Louis (STL)

A restaurant and a gym are featured at this hotel. Free self parking, a coffee shop, and dry cleaning are also offered.

Courtyard by Marriott St. Louis Downtown/Convention Center

Downtown St. Louis

Save 100% on your flight

$387

per person

Nov 13 - Nov 16

found 8 hours ago

Roundtrip flight included

Dallas (DFW) to St. Louis (STL)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a business center, and a coffee shop are also offered.

Hilton Garden Inn Chesterfield

$583

per person

Nov 6 - Nov 9

found 17 hours ago

Roundtrip flight included

Boston (BOS) to St. Louis (STL)

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

$87 nightly

$101 total

Oct 1 - Oct 2

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

Sep 29 - Sep 30

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

Hyatt Place St. Louis/Chesterfield

333 Chesterfield Center East, Chesterfield, MO

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$147 total

Oct 5 - Oct 6

Total with taxes and fees

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

Pool

Breakfast included

Drury Plaza Hotel St. Louis at the Arch

2 South 4th Street, St. Louis, MO

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$140 total

Sep 29 - Sep 30

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free buffet breakfast each morning.

Pool

Hot Tub

Clayton Plaza Hotel & Extended Stay

7750 Carondelet Avenue, St. Louis, MO

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$115 total

Oct 5 - Oct 6

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

$125 nightly

$147 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

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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.

Popular places to visit

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's acclaimed art scene or attend a baseball game.

St. Louis Union Station

You can learn about the local history of St. Louis when you make a stop at a well-known site like St. Louis Union Station. Experience the area's acclaimed theater scene or attend a baseball game.

Gateway Arch

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Frequently asked questions

How much are vacation packages to Chesterfield?

Travelocity has flight and hotel vacation packages from an incredible $274. 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.