Title: The Best 5 Star Hotels in Chester, IL  | 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)[Chester Vacation Packages](https://expedia.com/Chester.d6139861.Destination-Travel-Guides)

![View of a serene sunset over the Mississippi River with a bridge and a boat, Chester, United States.](https://images.trvl-media.com/place/6139861/daaedb53-d06a-4dd2-a501-e90fa192b410.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6139861/daaedb53-d06a-4dd2-a501-e90fa192b410.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Chester 5 Star Hotels

Tonight

[Feb 28 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-02-28&endDate=2026-03-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 1 - Mar 2](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-03-01&endDate=2026-03-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-03-06&endDate=2026-03-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chester.

![Urban Lofts](https://images.trvl-media.com/lodging/40000000/39930000/39926100/39926011/1b66adae_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Urban Lofts

104 North Jackson Street Perryville MO

[Get rates](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=39926011&PinnedHotelID=39926011&HadPinnedHotel=true&regionId=6139861)

[](https://expedia.com/Perryville-Hotels-Urban-Lofts.h39926011.Hotel-Information)

Still don't see what you're looking for?

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You can also use these popular filters to refine your search.

[Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&regionId=6139861&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&regionId=6139861&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&regionId=6139861&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&regionId=6139861&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&regionId=6139861&star=50&star=50&amenities=WATER_PARK)

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.

## Chester and related destinations

- Chester
- Hartwell
- Eastland
- Leesville
- Brownwood

Cartoon fans flock to the birthplace of Popeye, where a riverside statue honors the spinach-loving sailor. Explore local history at Fort Kaskaskia or ring the Kaskaskia Bell, a symbol of American independence.

[See all hotels in Chester](https://www.expedia.com/Hotel-Search?startDate=2026-03-15&endDate=2026-03-16&adults=2&regionId=6139861)

![View of a serene sunset over the Mississippi River with a bridge and a boat, Chester, United States.](https://images.trvl-media.com/place/6139861/daaedb53-d06a-4dd2-a501-e90fa192b410.jpg?impolicy=fcrop&w=900&h=533&p=1&q=high)

## Top Chester Hotel Reviews

## Find out more about Chester

Pamper yourself on your impending break. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Chester so popular in the last year. There's no reason to delay a getaway to Chester any longer. Furthermore, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. Book one of Expedia's luxurious 5-star hotels in Chester and get ready to be pampered like never before. Don't wait any longer!

### 5-Star Hotels in Chester

Don't be afraid to demand the best service from your hotel, along with the best conditions. Excellent customer care, spacious rooms, and rejuvenating spa offerings are waiting for you. You're sure to find exactly the accommodation you need. Not only that, the hotels in this area receive fantastic marks for customer satisfaction, so you know you'll be looked after during your getaway. What creature comforts do you want in your lodging? 24-hour room service, so you can order that Turkish coffee in the wee hours of the morning? A body scrub that will leave you feeling outstanding? Butler services? No matter what you want on a perfect getaway, you're bound to find it here. 

But you aren't going to spend your entire vacation in your room, of course. Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Chester are the perfect place to rest up after an exciting day. Ready to learn more? Plenty of visitors recommend this location. 

### Make Your Escape

The results are in, and Chester 5-star hotels are the place to be when you book your next vacation. Additionally, these accommodations are highly rated -- 100% of visitors recommended 5-star hotels in Chester! Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Opt for one of the 5-star hotels in Chester today and relax in the lap of luxury tomorrow.

## Frequently asked questions

### How much does it cost to stay in a 5-star hotel in Chester?

> - Search for the lowest price per night

### What makes a hotel 5 stars in Chester?

### Are there any 5-star all-inclusive resorts in Chester?

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