Chester Trips (flight + hotel)

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Top hotels in Chester

Baymont by Wyndham Chester IL
Baymont by Wyndham Chester IL
2.5 out of 5
2150 State Street, Chester, IL
Fully refundableReserve now, pay when you stay
The price is P4,727 per night from 15 Jan to 16 Jan
P4,727
P5,246 total
includes taxes & fees
Jan 15 - Jan 16
8.6/10 Excellent! (214 reviews)
"I had an issue with the TV screen frozen and was not able to enjoy the use of the TV, before going to sleep. Mentioned it to the front desk, said they would look into this, but was not fixed. Also, notice they did not refresh the room for my second day stay. Reused towels."

Reviewed on May 1, 2023

Baymont by Wyndham Chester IL
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
2.5 out of 5
1001 Veterans Blvd, Festus, MO
Fully refundableReserve now, pay when you stay
The price is P4,940 per night from 19 Jan to 20 Jan
P4,940
P5,649 total
includes taxes & fees
Jan 19 - Jan 20
7.8/10 Good! (728 reviews)
"very convenient location"

Reviewed on Jan 4, 2025

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Holiday Inn Express & Suites Perryville, an IHG Hotel
Holiday Inn Express & Suites Perryville, an IHG Hotel
2.5 out of 5
2020 Jefferson St, Perryville, MO
Fully refundable
The price is P5,078 per night from 6 Feb to 7 Feb
P5,078
P5,813 total
includes taxes & fees
Feb 6 - Feb 7
9.2/10 Wonderful! (432 reviews)
"Very friendly staff and good breakfast"

Reviewed on Jan 4, 2025

Holiday Inn Express & Suites Perryville, an IHG Hotel
See all 132 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.

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination on Expedia. But how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
If you’d like to score a cheap Chester vacation package, consider visiting in December, January and February. You’ll usually find lower rates on flights and accommodations during these months — ideal for travelers wishing to save money.
How many days is enough for Chester?
With a well-organized itinerary, you can easily tick off the most popular Chester attractions in a few days. But if you’d like to discover hidden gems or go on day trips, consider booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Elzie C. Segar Memorial Park among the many things to keep you busy. 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?
Begin your search for a Chester package deal by entering your destination and preferred travel dates under our “Packages” tab. Then add a few filters, like “Popular locations” and “Property type,” to tailor the results to your exact needs. You can also sort by “Package discount” and browse offers that come with irresistible savings. If you don’t find the perfect Chester package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chester escape underway.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation package. Click on the “Package” heading, then enter your destination and travel dates to see 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 land a better deal.
When to book a vacation package to Chester?
If you’re planning a spur-of-the-moment Chester adventure, browse our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Chester?

  1. Choose your travel dates: The things you want to do in Chester and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may come up during your trip to Chester.
  3. Decide how long to go away for: Now that you’re more familiar with Chester, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Chester vacation package.

Popular places to visit

Elzie C. Segar Memorial Park

Explore the great outdoors at Elzie C. Segar Memorial Park, a lovely green space in Chester. Discover the area's museums and shops.

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