Chester Vacation Packages

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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.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Sep 13 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.2/10 Very Good! (760 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul. 26, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Sep 13 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
9.2/10 Wonderful! (1,558 reviews)
We stay here often. It is central to our needs and we like the dining choices that are nearby. The facility is always neat and clean, the parking is convenient and the staff are always friendly, professional and ready to help. We find it to be a nice relaxing atmosphere and a great place to get a good nights rest.

Reviewed on Aug. 14, 2025

Comfort Suites Rolla

Comfort Suites Rolla

2.5 out of 5
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (872 reviews)
The room had a musty odor - bathroom was not as clean as should be , bed covers sheets felt damp Food area was nice and options were good reserved king suite ended up with handicap shower room

Reviewed on Aug. 13, 2025

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.6/10 Excellent! (114 reviews)
It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay.

Reviewed on Jul. 9, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.4/10 Very Good! (1,001 reviews)
Loved my stay here will be back

Reviewed on Aug. 13, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

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 CA $103 per night from Sep 7 to Sep 8
CA $103
CA $114 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very Good! (326 reviews)
"just a nice clean place to stay, not very far from shooting complex at Sparta"

Reviewed on Aug. 4, 2025

Baymont by Wyndham Chester IL
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

3 out of 5
1001 Veterans Blvd, Festus, MO
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Aug 24 to Aug 25
CA $155
CA $178 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (828 reviews)
"Truly amazed by the speed of check-in. The clerk on duty had her paperwork all ready, spread out on a desk. She seemed to guess which guest I was and just handed over the document to initial. Perfect efficiency! Also, she was pleasant. The lobby, stairs and hallways had been recently upgraded. Room ..."

Reviewed on Jul. 21, 2025

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
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 CA $131 per night from Aug 17 to Aug 18
CA $131
CA $150 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (495 reviews)
"I thought that this property had just been constructed as everything was brilliant. Staff was super nice and knowledgeable about the area. 100% would recommend to anyone needing to visit the area or passing through."

Reviewed on Aug. 11, 2025

Holiday Inn Express & Suites Perryville by IHG
See all 147 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.
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Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from CA $805 on Expedia, you'll be surprised at how little a vacation to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
December, January and February are great times to look for cheap Chester vacation packages. Opting to travel in less busy periods means you can typically find better prices on flights and hotels.
How many days is enough for Chester?
With a well-organized itinerary, you can easily visit the most popular Chester attractions in a few days. But if you'd like to discover hidden gems or go on day trips, think about booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
It's easy to see why a Chester vacation is on the must-do list of many travellers. Well-known attractions like Elzie C. Segar Memorial Park are just the beginning of things to keep you busy here.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Chester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Chester vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Chester?
Enjoy incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Chester vacation.
How to plan a trip to Chester?

  1. Pick your travel dates: What you want to do in Chester and your preferred season can help you decide when to get away.
  2. Set a budget: Factor in costs such as flights, transportation and food when working out how much to set aside for your trip to Chester. Then, select a hotel that fits your budget, whether that's a low-cost option or a more upscale retreat.
  3. Work out your trip length: Consider how long you'd like to spend discovering Chester. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the perfect Chester vacation package for you.

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