Chester Vacations from $630
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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
- The West End
Dec 21 - Dec 27The West End + Flight
Central West End6 nights2.0 star property8.6/10 - Excellent (715 reviews)"Room was clean!! Kitchen was useful and clean. Would stay here again."Reviewed November 11, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop$746$630found 1 day agoper traveler - The Wildwood Hotel
Dec 21 - Dec 27The Wildwood Hotel + Flight
Wildwood6 nights3.5 star property9.2/10 - Wonderful (1,679 reviews)"Was clean, room was large and comfortable. Bed was comfortable and stay was very relaxing. Nice simple breakfast with both packaged and fresh food, Was away from the city so was quieter, than staying in other towns. Staff was very friendly and helpful."Reviewed November 12, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop$1,188$716found 1 day agoper traveler - Moonrise Hotel
Dec 21 - Dec 27Moonrise Hotel + Flight
Delmar Loop6 nights4.0 star property9.0/10 - Wonderful (2,051 reviews)Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop$1,089$858found 1 day agoper traveler - The Cheshire
Dec 21 - Dec 27The Cheshire + Flight
Richmond Heights6 nights4.0 star property8.8/10 - Excellent (1,001 reviews)Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop$1,115$882found 1 day agoper traveler - Ameristar Casino Resort and Spa
Dec 18 - Dec 22Ameristar Casino Resort and Spa + Flight
St. Charles4 nights4.5 star property8.8/10 - Excellent (1,088 reviews)"We were here for a wedding. Our room was very nice but my son’s bathroom was disgusting and not clean, they had to switch rooms and the only compensation they gave them was a food voucher. Not acceptable with blood and vomit not cleaned from previous guest. We expected more for this caliber of hotel."Reviewed November 8, 2026Roundtrip • Denver (DEN) - St. Louis (STL)DEN - STL • Nonstop STL - DEN • Nonstop$782$662found 1 day agoper traveler
Where to stay in and around Chester
Ste Genevieve
Discover Ste Genevieve, a charming destination perfect for families, nature lovers, and history enthusiasts seeking a memorable getaway. With attractions like Hawn State Park for outdoor adventures, the historic Ste. Genevieve Historic District for a glimpse into the past, and Pere Marquette Park for leisurely strolls, there’s something for everyone. Located about 36 miles by car from Chester, Ste Genevieve offers a diverse range of experiences and is a smart choice for your next hotel booking.
St Mary
Plan your stay in St Mary, a top-rated choice for family and nature enthusiasts looking for a refreshing weekend getaway. This charming city offers access to outdoor adventures like golfing and exploring the scenic national state park, while landmarks like Fort Kaskaskia and Elzie C. Segar Memorial Park provide rich historical and recreational experiences. Located about 13 miles by car from Chester, St Mary is a smart choice for travelers seeking a blend of relaxation and exploration.
Menard
If you are a family or nature enthusiast, look no further than Menard, a charming village known for its scenic beauty and outdoor activities. With attractions like the historic Fort Kaskaskia, the quirky Popeye Museum, and the serene Mitchell Island, Menard offers a delightful mix of exploration and leisure. Located about 5 miles from Chester, this destination ensures easy access while providing a peaceful getaway. Menard's blend of nature and culture makes it a smart choice for your vacation stay.
Bremen
Ideally situated for family travelers and those seeking a weekend getaway, Bremen offers a charming base for exploring the historic Mary's River Covered Bridge, the scenic Randolph County State Recreation Area, and the iconic Kaskaskia Bell. This village, nestled in Chester, welcomes visitors year-round, with peak arrivals in summer. Bremen's accessibility makes it a smart choice for your next trip, providing a perfect blend of relaxation and adventure.
Kaskaskia
Travelers visiting the area often choose Kaskaskia, especially those with an affinity for history, family, and nature. This charming village offers a unique blend of outdoor experiences and scenic beauty, with attractions like the historic Fort Kaskaskia, the whimsical Popeye Museum, and the serene Mitchell Island. With visitor numbers peaking in June to July and November, Kaskaskia provides a welcoming atmosphere year-round, located about 5 miles from Chester, making it a smart choice for your stay.
Discover the most popular places to visit in Chester
Chester Hotel Deals
"Nice, big building with big, comfy lobby. We were at the end of a long hallway so it was nice and private for us. Woman in charge was very pleasant and competent. Got us checked in right away."
Holiday Inn Express Hotel & Suites Sparta by IHG
Holiday Inn Express Hotel & Suites Sparta by IHG
"A pitch perfect stay"
"When you just need a clean bed, shower, and AC, this is it! The only thing we really missed was coffee… and there’s a gas station down the road. Friendly helpful owner. We even chatted with others staying here. It’s a very “down home” place to stay."
"Staff had to be contacted via doorbell to come and assist - upon check-in, the attendant was at Wal Mart. Towels were dingy/not white, and bed sheets and pillowcases were the same. Neither staff person (one male and one female) ever smiled - hospitality seemed to be a nuisance. Quite disappointing, but in this day and age, hospitality employees are not taught the importance of customer service."
Sparta Motel Near St. Louis / Mississippi River IL
Sparta Motel Near St. Louis / Mississippi River IL
Holiday Inn Express & Suites Perryville by IHG
Holiday Inn Express & Suites Perryville by IHG
Microtel Inn & Suites by Wyndham Sainte Genevieve
Microtel Inn & Suites by Wyndham Sainte Genevieve"Refrigerator in the room did was not cold. Did not get cold all night TV in the room. Had to call maintenance to fix it. Overall it was a good stay. Just need to fix the fridge"
Find out more about Chester
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.
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.
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.
Frequently Asked Questions
How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination from $630 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.