
Deals on vacations and trips to Chester
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Chester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Hotel Indigo Rochester – Mayo Clinic Area by IHG
Downtown Rochester
Price was $697, price is now $524 per person
$524
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a rooftop terrace on site, and a 24-hour front desk and a snack bar/deli are also provided.

Aspen Select
Price was $698, price is now $538 per person
$538
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a terrace are also provided.

The Berkman
Folwell
Price was $868, price is now $718 per person
$718
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This aparthotel features a gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free WiFi. Self parking, a 24-hour business center, and a terrace are also offered.

Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys
Kutzky Park
Price was $954, price is now $795 per person
$795
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and WiFi in public areas. Self parking, a 24-hour business center, and a terrace are also offered.

Kahler Inn and Suites - Mayo Clinic Area
Downtown Rochester
Price was $870, price is now $729 per person
$729
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free self-serve breakfast each morning.
Top Chester hotels deals

AmericInn by Wyndham Osage
2212 Highway 218 Osage IA
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $102 total per night
$102 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub

Super 8 by Wyndham Cresco IA
511 Second Ave SE, Hwy 9 & 5th Street Cresco IA
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $75 total per night
$75 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free on-the-go breakfast each morning. A safe deposit box is provided and the front desk is staffed around-the-clock.
Breakfast included
Pet friendly

Americas Best Value Inn & Suites Spring Valley
745 N Broadway St Spring Valley MN
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $94 total per night
$94 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and laundry facilities and free newspapers are also offered.
Breakfast included
Pet friendly

Country Trails Inn & Suites
809 U.S. 52 Preston MN
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $126 total per night
$126 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
An attached winery and an indoor pool are featured at this smoke-free hotel. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas and a fireplace in the lobby are also provided.
Pool
Hot Tub

Western Inn & Suites
1530 Main St, Osage IA
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $71 total per night
$71 total
Dec 23 - Dec 24
Total with taxes and fees
The motel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
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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