Title: Chester Vacation Packages 2026 from $457 | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx6139861)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6139861.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d6139861.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6139861.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6139861.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6139861/daaedb53-d06a-4dd2-a501-e90fa192b410.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Vacations from $457 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, 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](https://www.expedia.com/Chester-Skating-Rink-Chester.d6183790.Vacation-Attraction), [Popeye Museum](https://www.expedia.com/Popeye-Museum-Chester.d553248621532655787.Vacation-Attraction) and [Marys River Covered Bridge](https://www.expedia.com/Marys-River-Covered-Bridge-Chester.d6183795.Vacation-Attraction). 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. ![Alhonna Resort LLC](https://images.trvl-media.com/lodging/79000000/78430000/78423900/78423853/843b5aa1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Alhonna Resort LLC $457 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included New York (NYC) to St. Louis (STL) 8.8/10 Excellent! (248 reviews) We had a nice stay the room was clean and comfortable. I felt safe and the pool was nice a warm. Easy to swim!!! Reviewed on Oct 28, 2025 ![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/800a6847_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wildwood Hotel Save 100% on your flight $567 per person Apr 24 - Apr 26 found 10 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 9.2/10 Wonderful! (1,600 reviews) Great staff. Safe place within walking distance of restaurants and activities. Clean room. Reviewed on Feb 19, 2026 ![Landing Apartments - Eureka](https://images.trvl-media.com/lodging/120000000/119980000/119975900/119975875/80055f3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Landing Apartments - Eureka Save 100% on your flight $1,004 per person Apr 8 - Apr 13 found 1 hour ago Roundtrip flight included Boston (BOS) to St. Louis (STL) No reviews ![Spacious 3-Bedroom with King Bed](https://images.trvl-media.com/lodging/110000000/109680000/109680000/109679988/f2203ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Spacious 3-Bedroom with King Bed Central West End Save 100% on your flight $977 per person Apr 8 - Apr 13 found 1 hour ago Roundtrip flight included Boston (BOS) to St. Louis (STL) 8.6/10 Excellent! (10 reviews) Clean room nice area Reviewed on Feb 1, 2026 ![The Cheshire](https://images.trvl-media.com/lodging/1000000/30000/26100/26061/b6ec06de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cheshire $625 per person Apr 24 - Apr 27 found 23 hours ago Roundtrip flight included Los Angeles (LAX) to St. Louis (STL) 8.6/10 Excellent! (1,002 reviews) Room was great breakfast was great Reviewed on Feb 14, 2026 Don't see what you're looking for? See all available trips from Columbus to Chester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-21/2026-03-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDH&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6139861) ### Discover the most popular places to visit in Chester #### Popeye Museum 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. [](https://expedia.com/Popeye-Museum-Chester.d553248621532655787.Vacation-Attraction) #### Fort Kaskaskia Learn about the local history of Ellis Grove when you spend time at Fort Kaskaskia. [](https://expedia.com/Fort-Kaskaskia-Illinois.d6183800.Vacation-Attraction) #### Mary's River Covered Bridge 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. [](https://expedia.com/Marys-River-Covered-Bridge-Chester.d6183795.Vacation-Attraction) ## Chester Hotel Deals ![Baymont by Wyndham Chester IL](https://images.trvl-media.com/lodging/1000000/10000/1700/1699/19091438_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Chester IL 2150 State Street Chester IL Fully refundableReserve now, pay when you stay $79 nightly $88 total Feb 22 - Feb 23 Total with taxes and fees 8.6/10 Excellent! (360 reviews) The rooms were extremely clean & the staff was supper attentive and nice! Reviewed on Feb 12, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=1699&PinnedHotelID=1699&HadPinnedHotel=true®ionId=6139861) ![Baymont by Wyndham Festus](https://images.trvl-media.com/lodging/1000000/10000/5600/5523/219ce8d0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Festus 1200 W. Gannon Drive Festus MO Fully refundableReserve now, pay when you stay $81 nightly $93 total Feb 24 - Feb 25 Total with taxes and fees 6.8/10 (935 reviews) Everything was great. I enjoyed my stay Reviewed on Feb 15, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F24%2F2026&endDate=2%2F25%2F2026&selected=5523&PinnedHotelID=5523&HadPinnedHotel=true®ionId=6139861) ![La Quinta Inn & Suites by Wyndham Festus - St. Louis South](https://images.trvl-media.com/lodging/1000000/50000/42200/42120/1887aa70_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Festus - St. Louis South 1001 Veterans Blvd Festus MO Fully refundableReserve now, pay when you stay $98 nightly $112 total Feb 22 - Feb 23 Total with taxes and fees 8/10 Very Good! (915 reviews) Very helpful staff at front deak Reviewed on Feb 20, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=42120&PinnedHotelID=42120&HadPinnedHotel=true®ionId=6139861) [See all 163 properties in Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F22%2F2026&endDate=2%2F23%2F2026®ionId=6139861) 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](https://www.expedia.com/Sparta-Country-Club-Sparta.d6187185.Vacation-Attraction), just 15 miles from Chester, where you can unwind in a serene environment. Enjoy sports and outdoor activities at [Perryville Country Club](https://www.expedia.com/Perryville-Country-Club-Perryville.d553248621564822920.Vacation-Attraction), 14 miles away. For relaxation, visit the [Illinois Caverns State Natural Area](https://www.expedia.com/Illinois-Caverns-State-Natural-Area-Illinois.d553248621532648577.Vacation-Attraction), 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: ](https://www.expedia.com/Fort-Kaskaskia-Illinois.d6183800.Vacation-Attraction)** 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: ](https://www.expedia.com/Popeye-Museum-Chester.d553248621532655787.Vacation-Attraction)** 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: ](https://www.expedia.com/Kaskaskia-Bell-Chester.d553248621532655788.Vacation-Attraction)** 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. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 32.9°F (0.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 36.0°F (2.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 46.9°F (8.3°C) | Light Rain | Mostly Sunny | Average | Average | | April | 56.1°F (13.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | May | 66.0°F (18.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 75.4°F (24.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 78.1°F (25.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 76.1°F (24.5°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 70.2°F (21.2°C) | Light Rain | Mostly Sunny | Average | Average | | October | 58.5°F (14.7°C) | Light Rain | Mostly Sunny | Average | Average | | November | 46.2°F (7.9°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | December | 38.5°F (3.6°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### 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](https://www.expedia.com/Randolph-County-State-Recreation-Area-Chester.d635036328994598912.Vacation-Attraction), [Chester Skating Rink](https://www.expedia.com/Chester-Skating-Rink-Chester.d6183790.Vacation-Attraction) and [Marys River Covered Bridge](https://www.expedia.com/Marys-River-Covered-Bridge-Chester.d6183795.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Chester vacation package cost? ### What are the cheapest months to go to Chester? ### How many days is enough for Chester? ### Is it worth booking a vacation package to Chester? ### How to find the best Chester package deals? ### Is it cheaper to book a Chester vacation as a package? ### When to book a vacation package to Chester? ### Does Expedia offer Book Now, Pay Later Chester vacation packages? ## Explore a world of travel 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