Deals on vacations and trips to Chesterfield

Save when you book Chesterfield package deals

Choose two or more items and save on your trip:

Chesterfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
Price was $755, price is now $604 per person
$604
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to St. Louis (STL)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a grocery/convenience store, and a lobby fireplace are also offered.
Hotel Saint Louis, Autograph Collection

Hotel Saint Louis, Autograph Collection

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $938, price is now $676 per person
$676
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
The Westin St. Louis

The Westin St. Louis

4.5 out of 5
Downtown St. Louis
Price was $907, price is now $715 per person
$715
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. Self parking, express check-out, and a computer station are also offered.
Hotel Indigo St. Louis - Downtown by IHG

Hotel Indigo St. Louis - Downtown by IHG

3.5 out of 5
Downtown St. Louis
Price was $779, price is now $621 per person
$621
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a snack bar/deli, and express check-in are also offered.
Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Price was $748, price is now $628 per person
$628
per person
May 8 - May 10
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, laundry facilities, and a virtual front desk are also on offer.

Top Chesterfield hotels deals

Super 8 by Wyndham Staunton

Super 8 by Wyndham Staunton

2 out of 5
1527 Herman Rd Staunton IL
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $79 total per night
$79 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A fireplace in the lobby and laundry facilities are also provided.
Breakfast included
Pet friendly
Memorable Family experiences at The Castle of Palmyra.

Memorable Family experiences at The Castle of Palmyra.

Palmyra IL
Get rates
This castle features a hot tub and a sauna. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden and laundry facilities are also provided.
Hot Tub
Free WiFi
Super 8 by Wyndham Jerseyville

Super 8 by Wyndham Jerseyville

2 out of 5
1303 State Highway 109 Jerseyville IL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $94 total per night
$94 total
Apr 5 - Apr 6
Total with taxes and fees
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.
Breakfast included
Pet friendly
Hampton Inn by Hilton Litchfield

Hampton Inn by Hilton Litchfield

2.5 out of 5
11 Thunderbird Circle Litchfield IL
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $124 total per night
$124 total
Mar 22 - Mar 23
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. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Carlin Villa Motel

Carlin Villa Motel

2.5 out of 5
18891 Rt 4 Old Rt 66 Carlinville IL
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $81 total per night
$81 total
Mar 12 - Mar 13
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and luggage storage are also on offer.
Parking included
Free WiFi
The Carlinville Cottage

The Carlinville Cottage

Carlinville IL
$471 nightly
The price is $484 total per night
$484 total
Mar 13 - Mar 14
Total with taxes and fees
This vacation home features laundry facilities.
Kitchen
Dryer
Don't see what you're looking for?
See all available properties in Chesterfield
View all properties
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.

Frequently asked questions

How much are vacation packages to Chesterfield?
Travelocity offers flight and hotel packages starting from just $604. With these kinds of savings, you'll be exploring all of Chesterfield before long.
Where can I get the best vacation package deals for Chesterfield?
No matter how you travel, Travelocity can help you find an unbeatable Chesterfield package deal. All you need to do is pick and choose between our 400 air carriers and 1,000,000 properties across the globe.
Why should I book my Chesterfield vacation package with Travelocity?
We've got experiences to suit every kind of globetrotter, excellent service and 24/7 customer support. To top that off, we'll match any lower price you're able to find with our Price Match Guarantee.
Will I save money on my Chesterfield car rental if I bundle it with hotels and flights?
Combining your flight, hotel and car into a Chesterfield vacation package is a great way to score better prices. Plus, having your own car rental gives you the freedom to make your way to all those big-name sights you're eager to check out. Situated 45 mi from Chesterfield, Busch Stadium is one place that should have a place on your itinerary. Top up the tank and make a day trip of it.
Which airport is best for Chesterfield?
Lambert-St. Louis Intl. Airport (STL), 40 mi southwest of the city center, is where many travelers begin their adventures in Chesterfield. But Abraham Lincoln Capital Airport (SPI) (45 mi away from central Chesterfield) could be more convenient for you.
Where should I stay when visiting Chesterfield?
If you're searching for a place to base yourself, check out the Mid-century Farmhouse- 35 acres- clean & quiet. It's the top choice for many travelers.

Photos of local treasures

Browse Chesterfield vacation photos for more inspiration