Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Hampton Inn & Suites Clayton/St. Louis-Galleria Area
Clayton
CA $893
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
Rooms could have been better cleaned prior to check in. Staff was very helpful
Reviewed on Aug 27, 2026
Hampton Inn & Suites St. Charles Old Town Area
CA $883
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9/10 Wonderful! (726 reviews)
The staff were always friendly and helpful. We had a comfortable room, though the shower door was broken.
Reviewed on Aug 26, 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 $114
CA $127 total
Sep 15 - Sep 16
includes taxes & fees
Baymont by Wyndham Festus
1200 W. Gannon Drive Festus MO
Fully refundableReserve now, pay when you stay
CA $93
CA $106 total
Sep 20 - Sep 21
includes taxes & fees
6.8/10 (1,001 reviews)
"Breakfast was good for the cost of room. Very friendly"
Reviewed on Aug 28, 2026
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
1001 Veterans Blvd Festus MO
Fully refundableReserve now, pay when you stay
CA $140
CA $160 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"air wasnt working"
Reviewed on Aug 23, 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.
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.
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.
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.
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.
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.
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.
Frequently asked questions
How much does a Chester vacation package cost?
Offering excellent value package deals from CA $839 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.
