Waterman Vacations
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Waterman Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $665, price is now $530 per person
$530
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Roman everything was clean everything was made that was all and it was very
Reviewed on Nov 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,033, price is now $731 per person
$731
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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.
1
Reviewed on Nov 4, 2026
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was $974, price is now $703 per person
$703
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (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
Price was $833, price is now $650 per person
$650
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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.
Breakfast was good
Reviewed on Nov 4, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was $727, price is now $572 per person
$572
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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.
Eurostars Magnificent Mile
Downtown Chicago
Price was $822, price is now $676 per person
$676
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
This is my 3rd time staying at Eurostars and it was excellent as it always has been! Clean rooms, I appreciate the overnight valet, and it is in a great/safe location.
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.