Chester Vacations from $409

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites - O'Fallon /Shiloh by IHG
The Wildwood Hotel
 White House at Grand Central
Spacious 3-Bedroom with King Bed
The Knight Center at Washington University
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Discover the most popular places to visit in Chester

Chester Hotel Deals

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
$66 nightly
The price is $73 total per night from Jan 25 to Jan 26
$73 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (353 reviews)
The hotel has been declining in recent years but the new management is working to make things better and they are doing a great job. Our room was very comfortable and clean. The staff were very friendly and helpful. It was an enjoyable experience and we will stay here again.

Reviewed on Dec 6, 2025

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

3 out of 5
1001 Veterans Blvd Festus MO
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $105 total per night from Jan 25 to Jan 26
$105 total
Jan 25 - Jan 26
Total with taxes and fees
7.8/10 Good! (905 reviews)
Clean room

Reviewed on Jan 12, 2026

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Silo Farm Haus- located in the heart of wine country!

Silo Farm Haus- located in the heart of wine country!

Ste. Genevieve MO
$326 nightly
The price is $347 total per night from Jan 20 to Jan 21
$347 total
Jan 20 - Jan 21
Total with taxes and fees
10/10 Exceptional! (148 reviews)
Super cute silo house and loved the welcome card, treats and coffeeMy husband is a carpenter and was amazed at the detail and expertise that went into building this Jessica was so nice and friendly and this special home reflected her hospitalityGreat little unique getaway!Beautiful scenic country ...

Reviewed on Dec 30, 2025

Silo Farm Haus- located in the heart of wine country!
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.

Find the Best Chester Vacation Packages

Things to do near Chester

Chester, Illinois, is perfect for outdoor enthusiasts and adventure seekers, offering a range of activities including a recreational area, campground, and local stores. Visitors can enjoy day trips, explore scenic spots, and indulge in spa retreats. For sports fans, there are various sporting venues to check out, making Chester a well-rounded destination for an exciting getaway.

Shopping

In Chester, visit local shops like The Blue Owl and The Antique Mall for unique gifts and souvenirs. If you're up for a drive, check out the nearby West Park Mall and the larger shops in Cape Girardeau for a wider selection.

Recreation

Experience luxury at Sparta Country Club, just 15 miles from Chester, where you can unwind in a serene environment. Enjoy sports and outdoor activities at Perryville Country Club, 14 miles away. For relaxation, visit the Illinois Caverns State Natural Area, 28 miles from Chester, and connect with nature.

Adventure

The World Shooting and Recreational Complex, located 19 miles from Chester, offers thrilling shooting sports and outdoor activities for enthusiasts. For a scenic hiking experience, head to Little Grand Canyon Trail Trailhead, 28 miles away, where you can enjoy breathtaking views and immerse yourself in nature.

Nightlife

Chester’s nightlife offers a cozy atmosphere with local bars and entertainment. Visit The Corner Tavern for a friendly vibe and craft beers. For a fun night, check out the Chester Country Club for live music and dancing, making it a great spot to unwind with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Chester

Chester, Illinois, is perfect for outdoor enthusiasts and adventure seekers, offering a blend of scenic beauty and rich history. Popular attractions include the Chester Racecourse, Chester Zoo, Chester Castle, and the stunning Chester Cathedral. Visitors can immerse themselves in the local culture while exploring historic sites and museums, making it an ideal destination for family experiences and outdoor fun.

  • Fort Kaskaskia: Explore the rich history of Fort Kaskaskia, a historic fortification that offers insights into early American frontier life. Nestled along the Mississippi River, the site provides a picturesque view and a glimpse into the cultural heritage of the region.
  • Popeye Museum: Celebrate the beloved cartoon character at the Popeye Museum, dedicated to the legacy of Elzie Crisler Segar, the creator of Popeye. This charming museum features memorabilia and exhibits that highlight the cultural impact of the iconic sailor and his friends.
  • Kaskaskia Bell: Visit the Kaskaskia Bell, a historic landmark with deep cultural significance. This iconic bell symbolizes the rich history of the region and offers visitors a unique connection to the past, making it a must-see for history buffs.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.9°F (0.5°C)Light RainMostly SunnySlightly LowSlightly Low
February36.0°F (2.2°C)Light RainMostly SunnySlightly LowSlightly Low
March46.9°F (8.3°C)Light RainMostly SunnyAverageAverage
April56.1°F (13.4°C)Light RainMostly SunnyAverageSlightly High
May66.0°F (18.9°C)Light RainMostly SunnyAverageSlightly High
June75.4°F (24.1°C)Light RainMostly SunnySlightly HighAverage
July78.1°F (25.6°C)Light RainMostly SunnySlightly HighSlightly High
August76.1°F (24.5°C)Light RainMostly SunnySlightly HighAverage
September70.2°F (21.2°C)Light RainMostly SunnyAverageAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November46.2°F (7.9°C)Light RainMostly SunnyAverageSlightly Low
December38.5°F (3.6°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Chester

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Chester during the low season (January to February and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chester Essential Information

Language
English
Currency
U.S dollars
Population
8,600
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Randolph County State Recreation Area, Chester Skating Rink and Marys River Covered Bridge

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Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination from $409 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?
You're likely to find reduced prices and greater availability in February, August and September. Take a look at our cheap Chester vacation packages and you could get some great off-season discounts.
How many days is enough for Chester?
The ideal length for your Chester vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to tick off all the main attractions and discover some hidden spots along the way.
Is it worth booking a vacation package to Chester?
It's no wonder a Chester vacation is on the to-do list of many travelers. Top attractions like Chester Skating Rink are just the start of things to see and do here.
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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester break is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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