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.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was $722, price is now $544 per person
$544
per person
Dec 22 - Dec 27
found 17 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Chicago (ORD)
Stay at this 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,923, price is now $1,411 per person
$1,411
per person
Dec 22 - Dec 27
found 9 hours ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,949, price is now $1,525 per person
$1,525
per person
Dec 22 - Dec 27
found 9 hours ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
Price was $908, price is now $720 per person
$720
per person
Dec 22 - Dec 27
found 17 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Good area for walking, eating
Reviewed on Nov 3, 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was $897, price is now $713 per person
$713
per person
Dec 22 - Dec 27
found 17 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Chicago (ORD)
Book a stay at this business-friendly 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 Grant Park and Soldier Field are located nearby.
The Godfrey Hotel Chicago
Downtown Chicago
Price was $763, price is now $616 per person
$616
per person
Dec 22 - Dec 27
found 17 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, 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.
Parking is the only issue with the locations. Options are limited with no in/out usability unless you valet park.
Reviewed on Nov 4, 2026
Top Hotel Deals
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
22.66 km from city center
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. ...
Holiday Inn Express & Suites Yorkville by IHG
577 E KENDALL DRIVE Yorkville IL
29.86 km from city center
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 ...
Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road Sycamore IL
24.08 km from city center
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. ...
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
17.27 km from city center
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 ...
Super 8 by Wyndham Rochelle
601 E Highway 38 Rochelle IL
28.97 km from city center
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 ...
The Montcler Hotel - Redberri Luxury Collection
3300 Drew Ave Sandwich IL
21.14 km from city center
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 ...
Best Western Rochelle Inn & Suites near DeKalb
1133 N. 7th St., Hwy 251 and Rt, 38 Rochelle IL
30.59 km from city center
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 ...
Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
17.44 km from city center
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 ...
Super 8 by Wyndham Yorkville
1510 A North Bridge St Yorkville IL
30.12 km from city center
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 ...
Motel 6 Sycamore, IL
1860 Dekalb Ave Sycamore IL
22.91 km from city center
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 ...
Comfort Inn DeKalb - University Area
W Lincoln Hwy, 1314,1314 DeKalb IL
18.07 km from city center
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
28.61 km from city center
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 ...
Super 8 by Wyndham DeKalb IL
800 W Fairview Dr DeKalb IL
15.49 km from city center
Book a stay at this business-friendly motel in DeKalb. Enjoy free breakfast, free WiFi, and free parking. Popular attractions River Heights Golf Course and Huskie ...
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.