Esmond Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Esmond Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$674
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,118
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Everything was awesome but there was no microwave and we needed one
Reviewed on Oct 3, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,487
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
$990
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago - River North
Downtown Chicago
$1,013
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Good location and parking, but the room has poor soundproofing, we can here the noise from outside
Reviewed on Oct 2, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$917
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
Radisson Hotel and Conference Center Rockford
200 South Bell School Road 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 ...
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 ...
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 ...
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 ...
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