Chester Vacations from $375

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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.
Valley Forge Casino Resort
Hyatt Centric Center City Philadelphia
Chateau Renault
Surrey Beach House
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City
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Discover the most popular places to visit in Chester

What to do 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
$88 nightly
The price is $95 total per night from Aug 21 to Aug 22
$95 total
Aug 21 - Aug 22
Total includes taxes and fees
7.4/10 Good! (573 reviews)
"The bus drivers were friendly and very helpful. The night agent wasn't as helpful as he could have been. I heard him give more information to another guest that could have been useful to me."

Reviewed on Aug 15, 2025

Comfort Inn Philadelphia International Airport West
Hilton Philadelphia at Penn's Landing

Hilton Philadelphia at Penn's Landing

4 out of 5
201 S. Christopher Columbus Blvd, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $167 total per night from Aug 31 to Sep 1
$167 total
Aug 31 - Sep 1
Total includes taxes and fees
8/10 Very Good! (1,334 reviews)
"Beautiful view"

Reviewed on Aug 16, 2025

Hilton Philadelphia at Penn's Landing
Sonesta Philadelphia Rittenhouse Square

Sonesta Philadelphia Rittenhouse Square

4 out of 5
1800 Market St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $138 total per night from Aug 31 to Sep 1
$138 total
Aug 31 - Sep 1
Total includes taxes and fees
8.2/10 Very Good! (1,918 reviews)
"Pretty much the stay was great just room placement.our room was by elevator and housekeeping so it was very noisey"

Reviewed on Aug 17, 2025

Sonesta Philadelphia Rittenhouse Square
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.

Things to do near Chester

Chester, Pennsylvania, offers a variety of activities perfect for family vacations, including educational experiences, an arena entertainment facility, and a vibrant shopping area. Tourists can enjoy travel guides, guided tours, and even ferry rides. For those seeking adventure, Chester provides excellent vacation packages that promise unforgettable experiences, making it an ideal destination for sports and city-themed getaways.

Shopping

For shopping in Chester, visit Sorella, just 5 miles away, offering a charming selection of gifts. If you're up for a drive, check out Reading Terminal Market and Chadds Ford Village & Barn Shops, both 13 miles away, providing a vibrant mix of local goods and entertainment.

Recreation

Experience the thrill of sports at Lincoln Financial Field, only 11 miles from Chester. Ice Works Skating Complex, just 4 miles away, offers exciting ice skating and adventure. For a cultural evening, enjoy a show at the Mann Center for the Performing Arts, located 12 miles from Chester.

Adventure

Experience the thrill of motor racing at Bridgeport Speedway, located 3 miles from Chester, where adrenaline meets excitement. For a scenic hike, explore the Underground Railroad Trail, 6 miles away, showcasing stunning landscapes. For water sports enthusiasts, Boathouse Row, 12 miles distant, offers adventurous activities on the water.

Nightlife

Chester's nightlife offers a vibrant mix of bars and entertainment. Check out The Brick Wall Tavern for a casual drink, and don’t miss the energetic atmosphere at Harrah's Philadelphia Casino for gaming and live shows. For a laid-back vibe, visit The Landing Kitchen by the river.

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

Find the best attractions near Chester

Chester, Pennsylvania, offers a variety of activities perfect for family, sports, and city-themed vacations. Explore modern colleges and universities, unwind in urban parks, and discover charming town neighborhoods. Visitors can immerse themselves in the local culture by visiting tourist attractions, delving into historic Chester, or enjoying performances at the Chester Playhouse. With plenty of options, there's something for everyone to enjoy while exploring this vibrant city.

  • Wells Fargo Center: Located 10 miles from Chester, the Wells Fargo Center is a premier entertainment venue known for hosting major sports events and concerts. The arena buzzes with family-friendly vibes, making it a perfect spot for an exciting night out.
  • University of Pennsylvania: Situated 11 miles away, the University of Pennsylvania boasts a stunning campus that combines modern architecture with rich history. Experience the vibrant city atmosphere as you stroll through this prestigious institution, known for its innovative programs and beautiful gardens.
  • Rittenhouse Square: Just 12 miles from Chester, Rittenhouse Square is a picturesque neighborhood offering lush green spaces, upscale dining, and boutique shopping. Enjoy the lively city vibes and relax in one of Philadelphia’s most beloved parks.

Best time to go to Chester

The best time to visit Chester is dependant 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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chester.
  • Consider traveling to Chester during the low season (January to March) for more affordable options.
  • 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.

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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $375 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.