Chester Vacations from $283

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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.
Lincoln Hotel Philadelphia
Hilton Garden Inn Philadelphia Center City
Club Quarters Hotel Rittenhouse Square, Philadelphia
Hyatt Centric Center City Philadelphia
Doubletree by Hilton Philadelphia Airport
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Discover the most popular places to visit in Chester

What to do in Chester

Chester Hotel Deals

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
$122 nightly
The price is $142 total per night from Jan 25 to Jan 26
$142 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (4,302 reviews)
Air conditioner was efficient. Excellent air quality. Safe and comfortable ambience. Always Appreciate all the amenities and hospitality and everything else. Thanks.

Reviewed on Jan 13, 2026

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
$114 nightly
The price is $133 total per night from Jan 23 to Jan 24
$133 total
Jan 23 - Jan 24
Total with taxes and fees
7.4/10 Good! (4,243 reviews)
Of course, the cookie is a delight when checking into the DoubleTree. The check-in was fast as well as the check-out. The room was perfect for me and I would gladly stay again.

Reviewed on Jan 12, 2026

Doubletree by Hilton Philadelphia Airport
The Windsor Suites

The Windsor Suites

4 out of 5
1700 Ben Franklin Pkwy Philadelphia PA
$124 nightly
The price is $145 total per night from Jan 27 to Jan 28
$145 total
Jan 27 - Jan 28
Total with taxes and fees
8.6/10 Excellent! (2,505 reviews)
Checking in the young lady, I believe her name was Ty. Got us squared away with our room lounge cars and explanations of the hotel. We were able to get extra towels and the Housekeeping staff was accommodating around our schedule to get the room addressed. Valet parking was a plus, we didn't have ...

Reviewed on Jan 12, 2026

The Windsor Suites
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.

Find the Best Chester Vacation Packages

Things to do near Chester

Chester, Pennsylvania, offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can enjoy exciting tours, explore local shopping centers and malls, and partake in outdoor fun. With options for beach vacations and excellent adventures, Chester is an ideal destination for those seeking a lively city experience while also enjoying nature. Whether you're planning a family trip or a city-themed getaway, Chester has something for everyone.

Shopping

For a unique shopping experience, check out Sorella, just 5 miles from Chester, offering a variety of gifts. If you're up for a drive, the Reading Terminal Market and Chadds Ford Village & Barn Shops, both 13 miles away, provide a lively atmosphere with diverse shopping options.

Recreation

Experience the excitement at Lincoln Financial Field, just 11 miles away, for thrilling sports events. Enjoy skating adventures at Ice Works Skating Complex, 4 miles from Chester. For a cultural night out, visit the Mann Center for the Performing Arts, 12 miles away, featuring captivating performances for the whole family.

Adventure

Experience the thrill of motorsport at Bridgeport Speedway, a mere 3 miles from Chester, where high-speed racing creates an exhilarating atmosphere. For a nature-filled adventure, hike the Underground Railroad Trail, located 6 miles away, offering stunning scenery and outdoor exploration. Don't miss the Narberth Tennis Club, 12 miles away, for some active fun.

Nightlife

Chester's nightlife offers vibrant experiences, from lively bars to cozy lounges. Check out the Chester Waterfront for scenic views and a drink, or explore local favorites like the Blue Rose Restaurant for a relaxed vibe. Enjoy live music at venues that keep the energy high well into the night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chester

Chester, Pennsylvania, is perfect for family outings and city-themed vacations, offering a mix of urban parks, charming neighborhoods, and modern college campuses. Visitors can explore local attractions such as the Chester Playhouse and delve into the city's rich history. Whether you're seeking cultural experiences or outdoor activities, Chester provides an engaging environment for everyone looking to enjoy a memorable getaway.

  • Wells Fargo Center: Experience thrilling sports and concerts at this vibrant arena, located 10 miles from Chester. With a lively atmosphere, it's a perfect spot for family entertainment and memorable events.
  • University of Pennsylvania: Explore the historic and modern campus of this prestigious institution, situated 11 miles away. The University offers a unique blend of academic excellence and urban energy, making it a fascinating place to visit.
  • Rittenhouse Square: Stroll through this picturesque neighborhood, located 12 miles from Chester. Rittenhouse Square is known for its beautiful park, upscale shops, and lively atmosphere, perfect for a relaxing afternoon in the city.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.3°F (0.7°C)Light RainMostly SunnySlightly LowSlightly Low
February35.6°F (2.0°C)Light RainMostly SunnyAverageSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnySlightly HighAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighSlightly High
July78.1°F (25.6°C)Light RainMostly SunnySlightly HighAverage
August76.1°F (24.5°C)Light RainMostly SunnyAverageAverage
September69.6°F (20.9°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnyAverageSlightly High
November46.8°F (8.2°C)Light RainMostly SunnySlightly LowAverage
December39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Chester

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Chester.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $283 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.