Chester Vacations from ￥193,206
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The Latest Chester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott St. Louis West County
￥197,208
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to St. Louis (STL)
9.2/10 Wonderful! (266 reviews)
Ive stayed here before. Rooms are nice because they have a desk kitchen snd couch. Bed was not good. We stayed here because our ac went out. I called and confirmed pet friendly booked and paid for the room only to arrive and be told its $100 pet fee. Thats not fair or ok.
Reviewed on Sep 4, 2026
The Cheshire
￥222,052
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
Just stayed one night with my husband but we want to come back. Good location, loved the British theme going, breakfast was excellent, fun exploring all the floors in the hotel as it has 4 floors. Did not visit the restaurants but I bet they were good and they gave us a coupon to user but we did not as we checked in late. Our room was quiet on the first floor. Good parking available. Staff were friendly and helpful during our whole stay. Loved the room author thing going on and labels on doors as it was fun to read, lots of good artwork, loved the author of your room having a book in the room like ours was Ann Sewell who wrote Black Beauty and we had a paper back copy of it in our room. If I was to ask for anything , it would be a small refrigerator as my husband travels with meds and a grab bar to step out of the tub.
Would highly recommend.
Reviewed on Sep 25, 2026
Find the Best Chester Vacation Packages
Chester Hotel Deals
Baymont by Wyndham Chester IL
2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
￥14,493
￥16,085 total
Oct 6 - Oct 7
includes taxes & fees
8.4/10 Very Good! (422 reviews)
"the room was super hot"
Reviewed on Sep 23, 2026
Holiday Inn Express & Suites Perryville by IHG
2020 Jefferson St Perryville MO
Fully refundable
￥16,514
￥18,904 total
Oct 4 - Oct 5
includes taxes & fees
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
7555 State Hwy Y French Village MO
￥15,885
￥25,191 total
Oct 26 - Oct 27
includes taxes & fees
10/10 Exceptional! (109 reviews)
"I loved everything about this cabin and I was on a high from this experience."
Reviewed on Sep 26, 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
Popeye Museum
9.4/10 (10 reviews)
Step into the world's only Popeye museum, showcasing rare memorabilia of the iconic sailor and his creator. Explore the Character Trail afterward to discover whimsical statues throughout Chester.
Cohen Memorial Home
This 1855 historic residence showcases distinctive blue storm windows and overlooks the Mississippi River. Tour the upstairs bedrooms with authentic furnishings or reserve the parlors for special events by appointment.
Fort Kaskaskia
9.6/10 (4 reviews)
Explore the earthen remains of this 18th-century French fortification, once protecting Illinois' first capital. Savor panoramic Mississippi River views while discovering colonial history at the interpretive overlook.
Chester Bridge
This historic 1942 structure spans the Mississippi River, connecting Illinois and Missouri with engineering elegance. Visit the nearby Welcome Center for panoramic river views and a glimpse of Chester's Popeye heritage.
Mary's River Covered Bridge
9.0/10 (6 reviews)
This historic 1854 covered bridge, the last of its kind in southern Illinois, showcases original white oak craftsmanship. Photographers capture its timeless charm against seasonal foliage in the peaceful countryside.
Kaskaskia Bell
10.0/10 (2 reviews)
Cast in 1741 by King Louis XV, the Liberty Bell of the West rang to celebrate America's independence in 1778. Press the button to enter the shrine and view murals depicting Kaskaskia's colonial history.
Elzie C. Segar Memorial Park
7.6/10 (4 reviews)
This riverside park honors Elzie Segar, Chester's native son who created the iconic Popeye character. Admire the 900-pound bronze Popeye statue while enjoying scenic Mississippi River views.
Randolph County State Recreation Area
9.0/10 (2 reviews)
Nestled among 1,101 acres of rolling hills, this recreation area offers serene lakeside activities and wooded trails. Reserve a campsite with electric hookups for the ultimate outdoor retreat surrounded by nature.
Frequently asked questions
How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination from ￥193,206 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?
- Choose your travel dates: The things you want to do in Chester and your preferred season can help you decide when to get away.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
