Waterman Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Waterman Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Wade
Downtown Chicago
$639
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$857
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,171
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
The Talbott, Autograph Collection
Downtown Chicago
$688
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Cute hotel in great location..make sure to ask for a street side room or your view will be a brick wall and the room will be like a dark cave. ðŸ˜
Reviewed on Sep 4, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
$1,288
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
$770
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Location and views from our room were excellent.
Reviewed on Sep 4, 2026
Top Hotel Deals
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
Book a stay at this business-friendly hotel in Sycamore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
The Montcler Hotel - Redberri Luxury Collection
3300 Drew Ave Sandwich IL
Book a stay at this business-friendly hotel in Sandwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Farnsworth House and Silver Springs ...
Holiday Inn Express & Suites Yorkville by IHG
577 E KENDALL DRIVE Yorkville IL
Book a stay at this spa hotel in Yorkville. Enjoy free breakfast, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Super 8 by Wyndham Yorkville
1510 A North Bridge St Yorkville IL
Book a stay at this business-friendly motel in Yorkville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Best Western Rochelle Inn & Suites near DeKalb
1133 N. 7th St., Hwy 251 and Rt, 38 Rochelle IL
Book a stay at this business-friendly hotel in Rochelle. Enjoy free parking, a 24-hour front desk, and a 24-hour business center. Our guests praise the helpful ...
Motel 6 Sycamore, IL
1860 Dekalb Ave Sycamore IL
Stay at this motel in Sycamore. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road Sycamore IL
Book a stay at this business-friendly hotel in Sycamore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Super 8 by Wyndham Rochelle
601 E Highway 38 Rochelle IL
Stay at this motel in Rochelle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Hampton Inn Yorkville
310 East Countryside Parkway Yorkville IL
Book a stay at this business-friendly hotel in Yorkville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn DeKalb - University Area
W Lincoln Hwy, 1314,1314 DeKalb IL
Book a stay at this business-friendly hotel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Huskie Stadium and NIU Convocation ...
Holiday Inn Express Rochelle by IHG
1240 North Dement Road Rochelle IL
Book a stay at this business-friendly hotel in Rochelle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Rochelle
567 E IL Route 38 Rochelle IL
Stay at this hotel in Rochelle. Enjoy free breakfast, free parking, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Quality Inn Sycamore - DeKalb
1475 South Peace Rd Sycamore IL
Book a stay at this spa hotel in Sycamore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
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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