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.
Eurostars Magnificent Mile
Downtown Chicago
$1,087
per person
Oct 20 - Oct 25
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,189
per person
Oct 20 - Oct 25
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Overall, Hotel Riu Plaza Chicago exceeded my expectations. Great location, great staff, good food, amazing views, and an unforgettable rooftop experience. I would definitely stay here again and recommend it to anyone visiting Chicago.
Reviewed on Sep 2, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$1,212
per person
Oct 20 - Oct 25
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Sports Illustrated Resorts Chicago
Downtown Chicago
$1,168
per person
Oct 20 - Oct 25
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$1,159
per person
Oct 20 - Oct 25
found 10 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Stay One Chicago
Downtown Chicago
$1,607
per person
Oct 20 - Oct 25
found 11 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, private pools, and 3 restaurants. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
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
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 ...
Embassy Suites by Hilton Rockford Riverfront
416 S Main Street Rockford IL
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 ...
Holiday Inn Express Hotel & Suites Rockford-Loves Park by IHG
7552 Park Place Road Loves Park IL
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 ...
Holiday Inn Rockford(I-90&Rt 20/State St) by IHG
7550 E State Street Rockford IL
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 ...
La Quinta Inn & Suites by Wyndham Rockford
7401 Walton St Rockford IL
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 ...
Econo Lodge Rockford Casino Area
7712 Potawatomi Trail Rockford IL
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
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 & Suites Beloit by IHG
3022 Ford Street Beloit WI
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 ...
Alpine Inn Rockford
4404 East State Street Rockford IL
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 ...
Woodspring Suites Loves Park Rockford
4101 GALLERIA DR Loves Park IL
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 ...
Home2 Suites by Hilton Loves Park Rockford
4150 N Bell School Road Loves Park IL
Book a stay at this business-friendly hotel in Loves Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Days Inn by Wyndham Rockford I-90 Casino District
220 S Lyford Rd Rockford IL
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Courtyard by Marriott Rockford
7676 E State St Rockford IL
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 ...
Sleep Inn Rockford I-90
725 Clark Drive Rockford IL
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Sep 24 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$314
Roundtrip
found 3 days ago
Thu, Sep 24 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$324
Roundtrip
found 4 days ago
Thu, Sep 24 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$349
Roundtrip
found 3 days ago
Thu, Sep 24 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$380
Roundtrip
found 4 hours ago
Best points of interest in Caledonia
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