Chester Vacation Packages
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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.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sofitel Philadelphia at Rittenhouse Square
Center City
CA $1,401
per person
Dec 29 - Jan 1
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
9.2/10 Wonderful! (2,780 reviews)
Great location clean room
Starting to look a little dated
But would stay there again
Reviewed on Oct 13, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Comfort Inn Philadelphia International Airport West
1300 Providence Ave Chester PA
Fully refundable
CA $120
CA $133 total
Nov 3 - Nov 4
includes taxes & fees
7/10 Good! (1,199 reviews)
"I spent one night here for a quick trip to Philly. The hotel is run down, my door was cracked. I wiped the room down with Clorox wipes and found some stains in the restroom wall near the sink. The bed was ok , just not as clean as I had expected due to the reviews . Parking was full so be prepared ..."
Reviewed on Oct 13, 2026
Club Quarters Hotel Rittenhouse Square, Philadelphia
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $198
CA $231 total
Oct 14 - Oct 15
includes taxes & fees
The Windsor Suites
1700 Ben Franklin Pkwy Philadelphia PA
CA $183
CA $213 total
Oct 28 - Oct 29
includes taxes & fees
8.8/10 Excellent! (3,331 reviews)
"Hotel room was dirty. Dust everywhere, someone’s food still in fridge."
Reviewed on Oct 13, 2026
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.
Stay near popular Chester attractions
Chester City Hall
7.8/10 (23 reviews)
After visiting Chester City Hall, make a plan to see the other sights and activities in Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
Subaru Park
7.0/10 (40 reviews)
Catch an event at Subaru Park during your trip to Chester. Amble around this family-friendly area's riverfront or attend a sporting event.
Harrah's Casino and Racetrack
7.6/10 (114 reviews)
Why not roll the dice with a visit to Harrah's Casino and Racetrack during your time in Chester? Experience the acclaimed art scene or attend a sporting event in this walkable area.
The Block Event Center at Harrahs Philadelphia
After visiting The Block Event Center at Harrahs Philadelphia, make a plan to see the other sights and activities in Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
WSFS Bank Sportsplex
Catch an event at WSFS Bank Sportsplex during your trip to Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
Crozier Park
Explore the great outdoors at Crozier Park, a lovely green space in Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
South Chester Market Place
You can search for that perfect souvenir at South Chester Market Place during your stay in Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
Veterans Memorial Park
After visiting Veterans Memorial Park, make a plan to see the other sights and activities in Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
What to do in Chester
Double Decker Hop-On Hop-Off City Sightseeing Philadelphia (1, 2, or 3-Day)
CA $69
per adult
90% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
CA $35
per adult
80% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
CA $83
per adult
82% of travellers recommend
Frequently asked questions
How much does a Chester vacation package cost?
You'll find cheap prices from CA $1,176 on Expedia for your Chester escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
January, February and March are the best times to look for cheap Chester vacation packages. Choosing to travel in quieter months means you can usually find lower prices on accommodations and flights.
How many days is enough for Chester?
Chester vacations come in various shapes and sizes, but to really get a feel for this destination, we reckon 2 days is a good ballpark. With this timeframe, you can fit in major attractions like John Heinz National Wildlife Refuge at Tinicum and Morton Morton House along with hidden gems. Don't skip neighbourhoods such as Springfield and Collingdale either. If you're clever with your time, you may even be able to take a day trip outside of Chester too.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Chester City Hall among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Chester vacation promises a good time for everyone.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Chester package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester escape off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
If you have your Chester vacation dates locked in, book as soon as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Chester?
- Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to visit Chester.
- Work out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Chester.
- Decide how long to go for: Now that you're up to speed on Chester, you can work out the right length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Chester vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
