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.
Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
7.6/10 Good! (5 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun. 8, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Very charming hotel. We felt like we were part of the Queens circle.

Reviewed on Jun. 11, 2025

Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9.4/10 Exceptional! (8 reviews)
Overall, we loved the apartment. It was cute, beds were very comfortable.

Reviewed on May 8, 2025

Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.8/10 Excellent! (812 reviews)
Staff at front desk helpful

Reviewed on Jun. 22, 2025

The Principal Hotel

The Principal Hotel

2 out of 5
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9.8/10 Exceptional! (71 reviews)
It's a really awesome space and the staff was excellent. The only issue we had was that the room had an odd chemical smell. It was a clean room so it may have been a ventilation issue. Other than that, everything was great!

Reviewed on Jun. 19, 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 $109 per night from Jul 6 to Jul 7
CA $109
CA $121 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (307 reviews)
"Very clean, but did not clean the room every other day. We were there for a week and they said they would come clean and give new towel ever other day, they did not."

Reviewed on Jun. 15, 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 CA $141 per night from Jun 29 to Jun 30
CA $141
CA $162 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 CA $111 per night from Jul 6 to Jul 7
CA $111
CA $124 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (574 reviews)
"Clean and affordable"

Reviewed on Jun. 13, 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from CA $923 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.