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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,695, price is now $1,062 per person
$1,062
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,974, price is now $1,161 per person
$1,161
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,502, price is now $1,608 per person
$1,608
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The hotel is beautiful. It has an amazing breakfast buffet, an amazing terrace with great drinks. The staff is super helpful and friendly. This hotel is a 10/10 for sure!
Reviewed on Aug 5, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,873, price is now $1,229 per person
$1,229
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,908, price is now $1,305 per person
$1,305
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Everything was great.
Reviewed on Aug 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,749, price is now $1,224 per person
$1,224
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
N/A
Reviewed on Aug 5, 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 parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
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 ...
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 ...
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 ...
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 ...
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 ...
Days Inn by Wyndham Rockford I-90 Casino District
220 S Lyford Rd Rockford IL
12.3 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 in our reviews. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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.