Search Deals on
Santa's Village Vacation Packages

Santa's Village Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this eco-certified 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
May 10 - May 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, a fitness center, and 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this boutique 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 Chicago Riverwalk and Michigan Avenue are located nearby.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
May 21 - May 25
just found
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.

3-4 Night Vacations in Santa's Village

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 9 - May 13
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

5-7 Night Vacations in Santa's Village

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)

Santa's Village Last Minute Hotel Deals

Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Chicago/Hoffman Estates
Country Inn & Suites by Radisson, Schaumburg, IL
Country Inn & Suites by Radisson, Schaumburg, IL
3 out of 5
1401 North Roselle Road, Schaumburg, IL
Stay at this 3-star family-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Country Inn & Suites by Radisson, Schaumburg, IL
Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hyatt Regency Schaumburg Chicago
Holiday Inn Chicago - Schaumburg by IHG
Holiday Inn Chicago - Schaumburg by IHG
3.5 out of 5
1998 North Roselle Road, Schaumburg, IL
Stay at this 3.5-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in ...
Holiday Inn Chicago - Schaumburg by IHG
Comfort Inn Chicago Schaumburg - O'Hare Airport
Comfort Inn Chicago Schaumburg - O'Hare Airport
2.5 out of 5
1300 E Higgins Rd, Schaumburg, IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Comfort Inn Chicago Schaumburg - O'Hare Airport
DoubleTree by Hilton Chicago Schaumburg
DoubleTree by Hilton Chicago Schaumburg
4 out of 5
800 National Pkwy, Schaumburg, IL
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful ...
DoubleTree by Hilton Chicago Schaumburg
HYATT house Chicago/Schaumburg
HYATT house Chicago/Schaumburg
3.5 out of 5
1251 American Lane, Schaumburg, IL
Stay at this 3.5-star business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
HYATT house Chicago/Schaumburg
Motel 6 Rolling Meadows, IL - Chicago Northwest
Motel 6 Rolling Meadows, IL - Chicago Northwest
2 out of 5
1800 Winnetka Cir, Rolling Meadows, IL
Stay at this motel in Rolling Meadows. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Motel 6 Rolling Meadows, IL - Chicago Northwest
See all 2,302 properties in Santa's Village
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.