Chester Vacation Packages
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Your Chester Vacation
Take the worry out of organizing your next big adventure with a Chester vacation package. Whether you're lured here by its food, entertainment or other highlights, this city offers countless exciting experiences to delve into. Make sure to spend time sightseeing during your trip to Chester. Lake Madison and Lakes Golf Course are some favorite places to visit. A few clicks is all it takes to put together a tailored Chester vacation on Expedia.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Valley Inn
University Heights
Price was CA $708, price is now CA $629 per person
CA $629
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Sioux Falls (FSD)
7.8/10 Good! (1,002 reviews)
Felt a big homey, beds nice, rooms clean, breakfast good.
Reviewed on Apr 1, 2026
Clubhouse Hotel Suites Sioux Falls
Mall District
Price was CA $1,049, price is now CA $911 per person
CA $911
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,035 reviews)
Room was great staff was friendly. Breakfast was well prepared. The only thing I was a little skeptical love was the pool and hot tub. It had a yellow tint to it and I didn’t smell any sense of like cleaning chemicals most pools you go to you smell a little chlorine of some sort, not here
Reviewed on Apr 8, 2026
Clarion Pointe Sioux Falls Airport
Northwest Sioux Falls
Price was CA $834, price is now CA $731 per person
CA $731
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Sioux Falls (FSD)
8.8/10 Excellent! (1,001 reviews)
They went out if there way to accommodate us. We had an over delayed flight and they helped us out and made our stay so comfortable. Very clean facilities and very comfortable. I wouldn’t hesitate to stay again.
Reviewed on Apr 6, 2026
Country Inn & Suites by Radisson, Sioux Falls
Downtown Sioux Falls
Price was CA $863, price is now CA $758 per person
CA $758
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Sioux Falls (FSD)
8.6/10 Excellent! (1,199 reviews)
Full swimming pool out of order. Staff requires a smile
Reviewed on Apr 10, 2026
Sleep Inn Sioux Falls Airport
Northwest Sioux Falls
Price was CA $785, price is now CA $696 per person
CA $696
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Sioux Falls (FSD)
7.6/10 Good! (1,004 reviews)
Was convenient for what we needed a room for.
Reviewed on Apr 7, 2026
Chester Hotel Deals
Royal River Casino and Hotel
607 S Veterans St Flandreau SD
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Apr 27 to Apr 28
CA $118
CA $150 total
Apr 27 - Apr 28
includes taxes & fees
8.6/10 Excellent! (595 reviews)
It was okay! Nothing spectacular.
Reviewed on Apr 3, 2026
AmericInn by Wyndham Hartford SD
1031 Diamond Circle Hartford SD
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Apr 26 to Apr 27
CA $113
CA $123 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (797 reviews)
Great hotel.
Reviewed on Mar 31, 2026
Best Western Plus Lakeview Hotel
456 SE 12th Madison SD
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Apr 23 to Apr 24
CA $192
CA $211 total
Apr 23 - Apr 24
includes taxes & fees
9.6/10 Exceptional! (234 reviews)
Great rooms, very clean, awesome breakfast
Reviewed on Mar 29, 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.
