Chester Trips (flight + hotel)

Top hotels in Chester

Baymont by Wyndham Chester IL
Baymont by Wyndham Chester IL
2.5 out of 5
2150 State Street, Chester, IL
Fully refundableReserve now, pay when you stay
The price is P4,399 per night from Jul 1 to Jul 2
P4,399
P4,882 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (304 reviews)
"the check in experience was great. Room was clean, beds were comfortable. Very convenient as a jumping off point to get to surrounding areas including Missouri and Illinois. Only reason for not 5 stars, pool was not open and breakfast was sparse with no refills at 815 in the morning. Improve the ..."

Reviewed on Jun 7, 2025

Baymont by Wyndham Chester IL
Holiday Inn Express & Suites Perryville by IHG
Holiday Inn Express & Suites Perryville by IHG
2.5 out of 5
2020 Jefferson St, Perryville, MO
Fully refundable
The price is P5,787 per night from Jun 29 to Jun 30
P5,787
P6,624 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (474 reviews)
"Was clean. Pool was nice. Breakfast was good"

Reviewed on Jun 12, 2025

Holiday Inn Express & Suites Perryville by IHG
Microtel Inn & Suites by Wyndham Sainte Genevieve
Microtel Inn & Suites by Wyndham Sainte Genevieve
2.5 out of 5
21958 Hwy 32, Ste Genevieve, MO
Fully refundableReserve now, pay when you stay
The price is P4,632 per night from Jul 6 to Jul 7
P4,632
P5,169 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (573 reviews)
Great Hotel - free breakfast- just ok
"Great Hotel but the breakfast was sorta lame to what Comfort Suites offer. Cereal, muffins, bagels, coffee, juices."

Reviewed on Jun 8, 2025

Microtel Inn & Suites by Wyndham Sainte Genevieve
See all 141 properties in Chester
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.

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination 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?
If you’d like to score a cheap Chester vacation package, consider visiting in December, January and February. You’ll usually find lower rates on flights and accommodations during these months — ideal for travelers wishing to save money.
How many days is enough for Chester?
With a well-organized itinerary, you can easily tick off the most popular Chester attractions in a few days. But if you’d like to discover hidden gems or go on day trips, consider booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Elzie C. Segar Memorial Park among the many things to keep you busy. Whether you’re heading away with the family or getting away with friends, a Chester vacation promises a good time for everyone.
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.
How to plan a trip to Chester?

  1. Choose your travel dates: The things you want to do in Chester and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may come up during your trip to Chester.
  3. Decide how long to go away for: Now that you’re more familiar with Chester, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Chester vacation package.

Popular places to visit

Elzie C. Segar Memorial Park

Explore the great outdoors at Elzie C. Segar Memorial Park, a lovely green space in Chester. Discover the area's museums and shops.

Elzie C. Segar Memorial Park

Chester Skating Rink

Enjoy an outing to Chester Skating Rink during your stay in Chester. Discover the area's museums and shops.

Chester Skating Rink

Chester Bridge

Chester Bridge is just one of the places to see in Chester, so why not enjoy the other things to explore during your travels? Amble around the area's parks or experience its entertainment venues.

Chester Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.