Chester Vacations from $337

Book a Hotel + Flight or Car together to unlock savings

Your Chester Vacation

With one of our vacation packages to Chester, you'll find countless opportunities for relaxation and adventure. There's loads to experience, including its rich history and cultural experiences. Make your trip to Chester even more fun by including some sightseeing. Swarthmore College, Harrahs Casino and Racetrack and Widener University are among the big attractions you'll want to explore. Whatever your travel plans or budget, putting together a tailored Chester vacation is a cinch with Expedia.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Philadelphia/ King of Prussia

Hyatt Place Philadelphia/ King of Prussia

3 out of 5
Save 100% on your flight
Price was $533, price is now $337 per person
$337
per person
Nov 22 - Nov 28
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8/10 Very Good! (1,069 reviews)
Everything is what I expected from a Hyatt Place except the shower head was awful for water volume and the bath sink was slightly clogged.

Reviewed on Oct 17, 2025

Moselem Springs Golf Club

Moselem Springs Golf Club

2 out of 5
Save 100% on your flight
Price was $893, price is now $510 per person
$510
per person
Dec 26 - Dec 28
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
No reviews
Tudor Place

Tudor Place

4 out of 5
Save 100% on your flight
Price was $732, price is now $477 per person
$477
per person
Nov 18 - Nov 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No reviews
Canopy by Hilton Philadelphia Center City

Canopy by Hilton Philadelphia Center City

4 out of 5
Center City
Price was $700, price is now $504 per person
$504
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
9.2/10 Wonderful! (1,868 reviews)
Beautifully decorated with a super friendly and helpful staff! Walkable to many fun areas - Reading Terminal Market only a few blocks away, and Washington Square and Rittenhouse Square not to far. The train station & airports (both Philly & Newark) are easy to get to on public transport as well. But again, the customer service and the way they checked in on us and were available even after check-out through their text chat for me was above and beyond. Special shout out to Felicia for helping me get back some left property!

Reviewed on Oct 16, 2025

One Sky Loft

One Sky Loft

2 out of 5
Center City
Save 100% on your flight
Price was $766, price is now $562 per person
$562
per person
Dec 3 - Dec 7
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
9.4/10 Exceptional! (46 reviews)
This is an awesome spot! We needed walking distance to Pennsylvania Hospital and this was it ! Spacious, all supplies provided, showers had great pressure .. only negative i can say is wood floors needed better cleaning, socks and bare feet were dirty .. overall, very nice place and would stay again!!

Reviewed on Oct 13, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chester
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Discover the most popular places to visit in Chester

Rittenhouse Square which includes street scenes and a park

Rittenhouse Square

Relax on grassy lawns, browse interesting sculptures and attend vibrant festivals at this historic square and popular city gathering point.

Rittenhouse Square
Pennsylvania Convention Center

Pennsylvania Convention Center

During your trip, find out what's happening at Pennsylvania Convention Center, a top convention center in Philadelphia. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

Pennsylvania Convention Center
If you can, get club box seats at the Flyers game for a great view and intimate bar and private restrooms, away from the crowds.

Wells Fargo Center

Catch an event at Wells Fargo Center during your trip to Philadelphia. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Wells Fargo Center

What to do in Chester

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

$25
per adult
82% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
Philadelphia: Museum of Illusions Timed Entrance Ticket

Philadelphia: Museum of Illusions Timed Entrance Ticket

$31
per adult
98% of travellers recommend
Philadelphia: Museum of Illusions Timed Entrance Ticket
Sphinx Gallery

Penn Museum Admission Ticket

$18
per adult
100% of travellers recommend
Penn Museum Admission Ticket
See all activities in Chester

Chester Hotel Deals

Comfort Inn Philadelphia International Airport West

Comfort Inn Philadelphia International Airport West

3 out of 5
1300 Providence Ave, Chester, PA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $101 total per night from Oct 22 to Oct 23
$101 total
Oct 22 - Oct 23
Total with taxes and fees
7.2/10 Good! (656 reviews)
"Clean"

Reviewed on Oct 16, 2025

Comfort Inn Philadelphia International Airport West
Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
1628 Chestnut St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $147 total per night from Nov 2 to Nov 3
$147 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (4,174 reviews)
"Great place!!!"

Reviewed on Oct 18, 2025

Club Quarters Hotel Rittenhouse Square, Philadelphia
Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
4509 Island Ave, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $131 total per night from Nov 2 to Nov 3
$131 total
Nov 2 - Nov 3
Total with taxes and fees
7.2/10 Good! (3,805 reviews)
"Fast and easy . Nice staff"

Reviewed on Oct 18, 2025

Doubletree by Hilton Philadelphia Airport
See all 3,076 properties in Chester
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.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Philadelphia Intl. Airport (PHL)
Population
34,100
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Philadelphia Museum of Art, Philadelphia Zoo and Mann Center for the Performing Arts

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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $337 on Expedia for your Chester break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
November, December and January are great times to look for cheap Chester vacation packages. Choosing to travel in quieter periods means you can generally find lower prices on flights and hotels.
How many days is enough for Chester?
Chester vacations come in various shapes and sizes, but to really sink your teeth into this place, we reckon 2 days is a good ballpark. In this timeframe, you can fit in top attractions like Chester City Hall and Widener University and track down some lesser-known spots. Don't forget to visit cool neighborhoods such as Springfield and Upland either. If you're smart with your time, you may even be able to take a day trip from Chester too.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Subaru Park among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Chester vacation promises a good time for everyone.
How to find the best Chester package deals?
Landing a cheap Chester package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most affordable Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chester?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Chester break.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Jet off on your dream escape to Chester with our Book Now, Pay Later vacations. No need to save like crazy or hold off until the next payday — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snag great deals while they last.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.