Chester Vacations from $530

You can snap up a vacation package to this popular destination from $530 on Expedia. However, how much your vacation to Chester costs will depend on factors like your hotel choice, length of stay and season.

September, November and December are great times to search for cheap Chester vacation packages. Choosing to travel in less busy months means you can usually find lower prices on accommodations and flights.

Allow at least 2 days for your Chester vacation if you’re hoping to take in all that makes this destination unique. Wander around popular neighborhoods, including Bellwood and Woodvale. Then tick off top sights like Parker’s Battery Park and The Lazy Daisy. With a well-planned itinerary, you’ll be kept busy with room for some relaxation too. Want to travel beyond Chester? Consider fitting in an excursion or two.

It’s no wonder a Chester vacation is on the to-do list of many travelers. Major attractions like Iron Bridge Sports Park are just the start of things to see and do here.

Bagging a cheap Chester package deal is a cinch with Expedia. After you’ve entered your destination and travel dates under our “Packages” tab, set your budget, apply a couple of filters and browse what’s available. You can fine-tune your search by “Amenities,” “Property type,” “Guest rating” and more. Sort the results by “Price: low to high” to discover the most wallet-friendly Chester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.

You can enjoy significant savings on your Chester break by booking a customized vacation package. Check the “Package” heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

Enjoy incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Chester getaway.

Your Chester break is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you a little more flexibility, we’ve teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.