Title: Chester Vacation Packages 2026 from $297 | 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 $297 ## 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. ![Ameristar Casino Resort and Spa](https://images.trvl-media.com/lodging/2000000/1880000/1873300/1873292/70b128db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ameristar Casino Resort and Spa Save 100% on your flight $297 per person May 30 - Jun 1 found 21 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 8.4/10 Very Good! (1,000 reviews) Overall it was a positive experience but we were VERY disappointed when we found out our daughter couldn’t swim all weekend. We would not have booked it if we had known that. Reviewed on Mar 22, 2026 ![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/035dee6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wildwood Hotel Save 100% on your flight $419 per person May 8 - May 12 found 24 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 9.2/10 Wonderful! (1,620 reviews) Awesome place to stay with kids. Nice pool and hot tub. Reviewed on Mar 24, 2026 ![Angad Arts Hotel St. Louis, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/28000000/27620000/27617000/27616925/25bc97a8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Angad Arts Hotel St. Louis, Tapestry Collection by Hilton Grand Center Save 100% on your flight $314 per person May 30 - Jun 1 found 1 day ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 8.8/10 Excellent! (1,065 reviews) Cleaning needs help in the rooms and bathrooms. Room 511 hopefully is the smallest of all the rooms. You couldn’t use the chair fully with the desk and had to take turns in areas it was so tight. The staff was wrong about times for the Terrance bar and restaurant causing us to wait for that and then miss the downstairs restaurant being open so we waited a few more hours to find a place to eat. Simple mistake but that’s their job. Reviewed on Mar 22, 2026 ![The Cheshire](https://images.trvl-media.com/lodging/1000000/30000/26100/26061/24983857_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cheshire Save 100% on your flight $496 per person May 8 - May 12 found 24 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 8.6/10 Excellent! (1,009 reviews) Very friendly staff. Reasonable price drinks Reviewed on Mar 22, 2026 ![Hilton Garden Inn Chesterfield](https://images.trvl-media.com/lodging/1000000/300000/297100/297075/40ccff19_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chesterfield Save 100% on your flight $464 per person May 8 - May 12 found 24 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 8.2/10 Very Good! (799 reviews) Room was clean. Had Netflix on tv Reviewed on Mar 16, 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/2026-04-26/2026-05-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDH&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Chester #### Popeye Museum 4.5/5(3 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. [](https://expedia.com/Popeye-Museum-Chester.d553248621532655787.Vacation-Attraction) #### Fort Kaskaskia 5/5(2 reviews) Learn about the local history of Ellis Grove when you spend time at Fort Kaskaskia. [](https://expedia.com/Fort-Kaskaskia-Illinois.d6183800.Vacation-Attraction) #### Elzie C. Segar Memorial Park 4/5(3 reviews) Explore the great outdoors at Elzie C. Segar Memorial Park, a lovely green space in Chester. Discover the area's museums and shops. [](https://expedia.com/Elzie-C-Segar-Memorial-Park-Chester.d6183802.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 $74 nightly $82 total Apr 5 - Apr 6 Total with taxes and fees 8.6/10 Excellent! (371 reviews) When I arrived no one was at front desk and receptionist didn't arrive until 10 min later from running an errand and noone seemed to be around to say she was out nor was there a sign to indicate will return soon. Room had bugs crawling in window seal, I was offered a new room further away. Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=1699&PinnedHotelID=1699&HadPinnedHotel=true®ionId=6139861) ![La Quinta Inn & Suites by Wyndham Festus - St. Louis South](https://images.trvl-media.com/lodging/1000000/50000/42200/42120/6e70629c_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 $101 nightly $116 total Mar 29 - Mar 30 Total with taxes and fees 8/10 Very Good! (933 reviews) The Hotel is close to the highway and many restaurants to choose from. Rooms could use a really good cleaning and cosmetic touch ups bathroom was starting to get mold around caulk in the shower. Elevator was out of order never seen any maintenance on the 3 days we were there. Making everyone use ... Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=42120&PinnedHotelID=42120&HadPinnedHotel=true®ionId=6139861) ![Holiday Inn Express & Suites Perryville by IHG](https://images.trvl-media.com/lodging/21000000/20120000/20115400/20115319/469821a6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express & Suites Perryville by IHG 2020 Jefferson St Perryville MO Fully refundable $95 nightly $109 total Mar 29 - Mar 30 Total with taxes and fees 9.2/10 Wonderful! (571 reviews) The young man who was at the check in desk has the best manners, super polite, kind and efficient. It was very nice to be welcomed by him!!! Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=20115319&PinnedHotelID=20115319&HadPinnedHotel=true®ionId=6139861) [See all 165 properties in Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F27%2F2026&endDate=3%2F28%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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