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 Felix River North/Magnificent Mile
Downtown Chicago
$542
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Check-in and check-out were a breeze. Very clean rooms, spacious bathroom. The room was smaller than expected, but perfect for my solo trip. Convenient location, 15 min walk from the river area, 8 min from the Michigan blvd. Aldi 5 min away, Starbuck 2 min away, Wallgreens 2 min away. Seemed pretty safe at night.
Reviewed on Sep 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$875
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Great location. So much to do in walking distance and hotel was great.
Reviewed on Sep 16, 2026
The Emily Hotel
Downtown Chicago
$717
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.
Comfortable room with a great view and luxuriously soft bed!
Reviewed on Sep 13, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
$750
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this business-friendly 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 Millennium Park and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
$869
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Clean room, nice location
Reviewed on Sep 15, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,364
per person
Nov 7 - Nov 11
found 24 hours ago
Roundtrip non-stop flight included
Fresno (FAT) 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.
Top Hotel Deals
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
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. ...
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. ...
Super 8 by Wyndham DeKalb IL
800 W Fairview Dr DeKalb IL
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.
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations