Rutland Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Rutland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$499
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
$684
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$604
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Staff was awesome and the property was spotless. Breakfast was the tops.
Reviewed on Sep 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,221
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Loved the great upgrade in room and the mini bar selection s
Reviewed on Sep 25, 2026
Level Chicago - River North
Downtown Chicago
$764
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Outstanding room. I highly recommend. Be sure to check out the 6th floor and all the amenities!
Reviewed on Sep 23, 2026
Park Hyatt Chicago
Downtown Chicago
$1,186
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Stay at this motel in Madison. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
Comfort Suites Madison West - Middleton
1253 John Q Hammons Dr Madison WI
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
DoubleTree by Hilton Madison Downtown
525 West Johnson Street Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
The Edgewater
1001 Wisconsin Place Madison WI
Book a stay at this luxury hotel in Madison. Enjoy a full-service spa, 4 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Baymont Inn & Suites by Wyndham Madison
2810 Coho Street Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Dylin
611 E Dayton St Madison WI
Stay at this aparthotel in Madison. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Camp Randall Stadium and Alliant ...
La Quinta Inn & Suites by Wyndham Madison American Center
5217 E Terrace Dr Madison WI
Stay at this hotel in Madison. Enjoy free parking, a fitness center, and WiFi (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. ...
Best Western Premier Park Hotel
22 S Carroll Street Madison WI
Book a stay at this spa hotel in Madison. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
AmericInn by Wyndham Madison South
101 W Broadway Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free parking, and a sauna. Our guests praise the breakfast and the helpful staff ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Dec 26 - Tue, Jan 5
BOS
Logan Intl.
MSN
Dane County Regional
$383
Roundtrip
found 2 days ago
Tue, Oct 6 - Tue, Oct 20
PDX
Portland Intl.
MSN
Dane County Regional
$397
Roundtrip
found 5 days ago
Tue, Oct 6 - Tue, Oct 20
PDX
Portland Intl.
MSN
Dane County Regional
$397
Roundtrip
found 5 days ago
Tue, Oct 6 - Tue, Oct 20
PDX
Portland Intl.
MSN
Dane County Regional
$611
Roundtrip
found 5 days ago
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