Caledonia Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Caledonia 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
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
12.03 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Riverview Inn & Suites, an Ascend Collection Hotel
700 W Riverside Blvd Rockford IL
15.89 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Rockford(I-90&Rt 20/State St) by IHG
7550 E State Street Rockford IL
12.57 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff ...
Econo Lodge Rockford Casino Area
7712 Potawatomi Trail Rockford IL
12.39 km from city center
Stay at this hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
AmericInn by Wyndham Beloit
2790 Milwaukee Rd Beloit WI
18.68 km from city center
Book a stay at this business-friendly hotel in Beloit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Express Hotel & Suites Rockford-Loves Park by IHG
7552 Park Place Road Loves Park IL
8.15 km from city center
Book a stay at this business-friendly hotel in Loves Park. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
Woodspring Suites Loves Park Rockford
4101 GALLERIA DR Loves Park IL
8.5 km from city center
Stay at this hotel in Loves Park. Enjoy free WiFi, free parking, and room service. Popular attractions Rivets Stadium and Rock Cut State Park are located ...
La Quinta Inn & Suites by Wyndham Rockford
7401 Walton St Rockford IL
13 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Embassy Suites by Hilton Rockford Riverfront
416 S Main Street Rockford IL
20.22 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, 2 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the helpful ...
Courtyard by Marriott Rockford
7676 E State St Rockford IL
12.59 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Alpine Inn Rockford
4404 East State Street Rockford IL
16.27 km from city center
Book a stay at this business-friendly motel in Rockford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
Holiday Inn Express & Suites Beloit by IHG
3022 Ford Street Beloit WI
18.57 km from city center
Book a stay at this business-friendly hotel in Beloit. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Sleep Inn Rockford I-90
725 Clark Drive Rockford IL
12.18 km from city center
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the overall ...
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.