Westville Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Westville Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Wade
Downtown Chicago
$639
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$857
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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 great location is perfect. Room was clean and updated. If I ever come back to Chicago I will stay here again. 10/10
Reviewed on Sep 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,171
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
The Talbott, Autograph Collection
Downtown Chicago
$688
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
The Ritz-Carlton, Chicago
Downtown Chicago
$1,288
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
$770
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Top Hotel Deals
Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Book a stay at this business-friendly hotel in New Buffalo. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive Michigan City IN
Book a stay at this spa hotel in Michigan City. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
Quality Inn Near Interstate I94
18830 Laporte Rd New Buffalo MI
Stay at this hotel in New Buffalo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Baymont by Wyndham New Buffalo
18800 Harbor Country Drive New Buffalo MI
Book a stay at this business-friendly hotel in New Buffalo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the clean rooms ...
Holiday Inn Express & Suites New Buffalo by IHG
11500 Holiday Dr New Buffalo MI
Stay at this hotel in New Buffalo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Microtel Inn & Suites by Wyndham Michigan City
9834 W 400 N Michigan City IN
Book a stay at this business-friendly hotel in Michigan City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
Baymont by Wyndham Michigan City
4128 South Franklin Street Michigan City IN
Book a stay at this business-friendly hotel in Michigan City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Pine Lake Resort and Banquets
444 Pine Lake Ave La Porte IN
Book a stay at this spa hotel in La Porte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Comfort Inn La Porte
100 Eastshore Court La Porte IN
Book a stay at this business-friendly hotel in La Porte. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
The Blue Heron Inn
1110 Lakeside Street La Porte IN
Book a stay at this business-friendly hotel in La Porte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Econo Lodge Portage
6101 MELTON RD BLDG A Portage IN
Stay at this hotel in Portage. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Founders' Square Park and East Branch are located ...
Comfort Inn Hobart-Merrillville I-65
1915 Mississippi St Hobart IN
Book a stay at this business-friendly hotel in Hobart. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20 Chesterton IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Tue, Feb 2 - Tue, Feb 9
DEN
Denver Intl.
SBN
South Bend Intl.
$275
Roundtrip
found 2 days ago
Sun, Dec 20 - Thu, Dec 31
MCO
Orlando Intl.
SBN
South Bend Intl.
$320
Roundtrip
found 3 days ago
Tue, Feb 2 - Sat, Feb 13
DEN
Denver Intl.
SBN
South Bend Intl.
$358
Roundtrip
found 2 days ago
Tue, Sep 15 - Tue, Sep 22
EWR
Newark Liberty Intl. Airport
SBN
South Bend Intl.
$377
Roundtrip
just found
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