Title: Chester Vacation Packages 2026 from $491 | 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 $491 ## Book a Hotel + Flight or Car together to unlock savings ## 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. ![Crowne Plaza St. Louis Airport by IHG](https://images.trvl-media.com/lodging/1000000/10000/3100/3010/90ecdcdc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Crowne Plaza St. Louis Airport by IHG Save 100% on your flight $491 per person Apr 20 - Apr 27 found 21 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 8/10 Very Good! (1,003 reviews) Centrally located, great park and fly, breakfast is great. The only thing I do not like is for police officers to park outside and go to eat breakfast. It appears that there is trouble at the hotel. Reviewed on Mar 9, 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 $884 per person Apr 20 - Apr 27 found 21 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 9.2/10 Wonderful! (1,626 reviews) We stayed for 1 night, overall good experience. The pool water was pretty cold and the hot tub is small (max occupancy 2). I was a little disappointed in the continental breakfast. Make your own waffles, cereal, and assorted breads. Wished for a larger selection and ready-made hot foods. Reviewed on Mar 8, 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 $765 per person Apr 20 - Apr 27 found 21 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 8.8/10 Excellent! (1,060 reviews) The property was beautiful and unique. The food was a disappointment. Unfortunately it was just too greasy for us. Reviewed on Mar 6, 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 $714 per person Apr 20 - Apr 27 found 21 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 8.6/10 Excellent! (1,001 reviews) Bar and restaurant were both great! Reviewed on Mar 9, 2026 ![The Knight Center at Washington University](https://images.trvl-media.com/lodging/39000000/38720000/38711900/38711810/a9bf89ab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Knight Center at Washington University Save 100% on your flight $666 per person Apr 20 - Apr 27 found 21 hours ago Roundtrip flight included Atlanta (ATL) to St. Louis (STL) 9.4/10 Exceptional! (486 reviews) The property locates on campus, convenient location. Newly renovated, quiet and clean. It would be great if the hotel can provide day time hot coffee in the lobby. Reviewed on Mar 9, 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/2026-04-10/2026-04-17/?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 #### 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) #### 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) ## 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 $82 nightly $91 total Mar 15 - Mar 16 Total with taxes and fees 8.6/10 Excellent! (366 reviews) Ok Reviewed on Mar 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=1699&PinnedHotelID=1699&HadPinnedHotel=true®ionId=6139861) ![Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy](https://images.trvl-media.com/lodging/111000000/110560000/110550900/110550817/d4a93b47_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy 7555 State Hwy Y French Village MO $134 nightly $144 total Mar 16 - Mar 17 Total with taxes and fees 9.8/10 Exceptional! (56 reviews) Absolutely amazing time as always. Staff is beyond great. Always ready to help and never in the way Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=110550817&PinnedHotelID=110550817&HadPinnedHotel=true®ionId=6139861) ![Microtel Inn & Suites by Wyndham Sainte Genevieve](https://images.trvl-media.com/lodging/1000000/430000/426000/425932/96e79bac_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Microtel Inn & Suites by Wyndham Sainte Genevieve 21958 Hwy 32 Ste Genevieve MO Fully refundableReserve now, pay when you stay $85 nightly $94 total Mar 29 - Mar 30 Total with taxes and fees 8.8/10 Excellent! (626 reviews) Booked a queen 2 bed with accessibility. Checked in, got to a room that had one queen bed and a shower over the tub! I was told they could not see what I booked, nothing they could do!I guess since a room is booked for two people it is ok to have to sleep together! Not if your just traveling together! ... Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=425932&PinnedHotelID=425932&HadPinnedHotel=true®ionId=6139861) [See all 163 properties in Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F11%2F2026&endDate=3%2F12%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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Savings not available on all packages.