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.
Moonrise Hotel
Delmar Loop
Price was CA $858, price is now CA $747 per person
CA $747
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to St. Louis (STL)
9/10 Wonderful! (1,944 reviews)
We love the Moonrise. It is clean, the room was spacious, the staff is friendly and helpful, there s do muchh to do on The Loop. The Loop Trolley is really cool!
Reviewed on Jun 7, 2026
Best Western St. Louis-Kirkwood Route 66
Price was CA $1,103, price is now CA $953 per person
CA $953
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to St. Louis (STL)
8.2/10 Very Good! (1,470 reviews)
Parking was good. Convenient location to Walmart, restaurants and not too far from St. Louis. Room was fine for price point.
Reviewed on Jun 8, 2026
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Price was CA $1,155, price is now CA $1,009 per person
CA $1,009
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to St. Louis (STL)
8.8/10 Excellent! (1,063 reviews)
Really unique place and wondefull rooftop
Reviewed on Jun 7, 2026
Hilton St. Louis Airport
Woodson Terrace
Price was CA $1,063, price is now CA $950 per person
CA $950
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to St. Louis (STL)
7.6/10 Good! (1,004 reviews)
We ate at the restaurant inside the lobby. It was good food and (probably) appropriately priced. We had two burgers and three beers for $63. The room we were in was a double queen. The bathroom could use some updating, but everything worked. The climate control was less than desirable and very difficult to figure out - not setting the temps, but getting the fan to run at the correct speed and interval. Press once and it takes 30 seconds to register. Then, the thermostat is mounted on front of the unit, causing short run times because the thermostat got too cold and shut it down. 30 seconds later, it would kick back on. After it finally cooled down, we were able to sleep fairly well.
Reviewed on May 30, 2026
Ameristar Casino Resort and Spa
Price was CA $990, price is now CA $900 per person
CA $900
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Room was large with separate sitting area. Shower was fantastic
Reviewed on Jun 5, 2026
Chester Hotel Deals
Baymont by Wyndham Chester IL
2150 State Street Chester IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jul 1 to Jul 2
CA $118
CA $131 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (396 reviews)
"No pool for kids"
Reviewed on Jun 1, 2026
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
1001 Veterans Blvd Festus MO
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Jun 17 to Jun 18
CA $117
CA $134 total
Jun 17 - Jun 18
includes taxes & fees
8/10 Very Good! (999 reviews)
"Check in was good. After we got back to the room around midnight the air conditioner wasn’t working properly. We tried the front desk 3 times & no answer, even walked down to front desk & couldn’t find anyone."
Reviewed on Jun 8, 2026
Baymont by Wyndham Festus
1200 W. Gannon Drive Festus MO
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Jul 5 to Jul 6
CA $103
CA $118 total
Jul 5 - Jul 6
includes taxes & fees
6.8/10 (970 reviews)
"It looks as if the property is undergoing a renovation. But it was still worthy of the stay. The renovation was not disruptive, or unsightly. Lots of parking close to a lot of different restaurants. Not far off the interstate as well. Would definitely book there again."
Reviewed on May 19, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
