Chester Vacation Packages
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Your Chester Vacation
With a Chester vacation package, say goodbye to endless planning and hello to an effortless adventure. Every detail of your escape has been taken care of before you depart, so you can spend more time experiencing this fantastic city. A trip to Chester is a wonderful opportunity to do a bit of sightseeing. Be sure to stop by well-known attractions like Chester Skating Rink, Popeye Museum and Marys River Covered Bridge. Expedia is here to help you escape the everyday. Tailor your vacation to Chester to suit your travel style, whatever that may look like.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ameristar Casino Resort and Spa
CA $944
per person
Nov 13 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to St. Louis (STL)
8.6/10 Excellent! (1,061 reviews)
Had a wedding here and paid almost $400 for a room after the hotel fees on site just to have a room with no AC we called the front desk around 9:30 and it was after 11 when maintenance finally arrived by then the wife and baby were asleep so I wasn’t going to let him wake them up so we just dealt with it. We also rented a movie paused it went downstairs then came back and couldn’t watch it also be careful what room you book I booked a king suite and that is not what I got the place was clean and most of the staff were ok but they disappointed me with the service to fix the AC and they weee sold out of rooms to get a different one
Reviewed on Sep 29, 2026
Hermann Grain Bins BNB
CA $2,385
per person
Nov 7 - Nov 13
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
6/10 (2 reviews)
It was so comfortable and uniquely and beautifully decorated! There was so many awesome areas to explore inside and outside of the Grain Bins. Food provided for breakfast was fresh and hot. There was perfectly cooked bacon, scrambled eggs and really moist corn muffins with homemade mango preservers! We were welcomed with fresh, homemade plum bread. Instructions for everything available to utilize and operate were easy to understand. I can’t wait to go back and I will tell all my friends and family about this unique and relaxing place.
Reviewed on May 22, 2026
The Cheshire
CA $1,205
per person
Dec 26 - Dec 29
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
It’s a unique (the rooms were named after authors 😊), and interesting hotel. The staff was friendly and helpful, the room was nice, and the breakfast was good. The only down side was the parking situation. We paid $10/day and many of the parking spots were filled by restaurant patrons (who parked for free). It was somewhat frustrating to drive around looking for a spot only to find out the only available spot was in lowest level of parking garage.
Reviewed on Sep 29, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Baymont by Wyndham Chester IL
2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
CA $127
CA $141 total
Oct 5 - Oct 6
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
CA $146
CA $167 total
Oct 31 - Nov 1
includes taxes & fees
9.2/10 Wonderful! (630 reviews)
"Check in and check out for 25 rooms was a breeze. Hotel room cards were ready as soon as we approached the hotel counter."
Reviewed on Sep 27, 2026
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
7555 State Hwy Y French Village MO
CA $143
CA $227 total
Oct 29 - Oct 30
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)
You can browse the exhibits at Popeye Museum, a museum with a story of its own, during your travels to Chester. Discover the area's museums and shops.
Fort Kaskaskia
9.6/10 (4 reviews)
Learn about the local history of Ellis Grove when you spend time at Fort Kaskaskia.
Cohen Memorial Home
Learn about the local history of Chester with a stop at Cohen Memorial Home. Amble around the area's parks or experience its entertainment venues.
Mary's River Covered Bridge
9.0/10 (6 reviews)
Learn about the local history of Chester when you take a trip to Mary's River Covered Bridge. Amble around the area's parks or visit its shops.
Chester Bridge
Chester Bridge is just one of the places to see in Chester, so why not enjoy the other things to explore during your travels? Amble around the area's parks or experience its entertainment venues.
Kaskaskia Bell
10.0/10 (2 reviews)
Find out about the history of Chester with a stop at Kaskaskia Bell. Discover the area's museums and shops.
Elzie C. Segar Memorial Park
7.6/10 (4 reviews)
Explore the great outdoors at Elzie C. Segar Memorial Park, a lovely green space in Chester. Discover the area's museums and shops.
Randolph County State Recreation Area
9.0/10 (2 reviews)
You can take time to visit Randolph County State Recreation Area during your travels to Chester. Amble around the area's parks or experience its entertainment venues.
Frequently asked questions
How much does a Chester vacation package cost?
Offering excellent value package deals from CA $944 on Expedia, you'll be surprised at how little a vacation to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
December, January and February are great times to look for cheap Chester vacation packages. Opting to travel in less busy periods means you can typically find better prices on flights and hotels.
How many days is enough for Chester?
With a well-organized itinerary, you can easily visit the most popular Chester attractions in a few days. But if you'd like to discover hidden gems or go on day trips, think about booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
It's easy to see why a Chester vacation is on the must-do list of many travellers. Well-known attractions like Elzie C. Segar Memorial Park are just the beginning of things to keep you busy here.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Chester vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Chester?
Enjoy incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Chester vacation.
How to plan a trip to Chester?
- Pick your travel dates: What you want to do in Chester and your preferred season can help you decide when to get away.
- Set a budget: Factor in costs such as flights, transportation and food when working out how much to set aside for your trip to Chester. Then, select a hotel that fits your budget, whether that's a low-cost option or a more upscale retreat.
- Work out your trip length: Consider how long you'd like to spend discovering Chester. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the perfect Chester vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
