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Chocolate Box Vacation Packages

Chocolate Box Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Price was $521, price is now $382 per person
$382
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $865, price is now $504 per person
$504
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $787, price is now $480 per person
$480
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,818, price is now $1,205 per person
$1,205
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $926, price is now $623 per person
$623
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,287, price is now $868 per person
$868
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,026, price is now $693 per person
$693
per person
Mar 12 - Mar 17
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,009, price is now $682 per person
$682
per person
Mar 4 - Mar 11
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $715, price is now $516 per person
$516
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa 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.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $630, price is now $459 per person
$459
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 Millennium Park and Soldier Field are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $742, price is now $544 per person
$544
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $873, price is now $640 per person
$640
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

3-4 Night Vacations in Chocolate Box

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $787, price is now $480 per person
$480
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $865, price is now $504 per person
$504
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $926, price is now $623 per person
$623
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,287, price is now $868 per person
$868
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Chocolate Box

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Save 100% on your flight
Price was $315, price is now $208 per person
$208
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $706, price is now $431 per person
$431
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,488, price is now $971 per person
$971
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,818, price is now $1,205 per person
$1,205
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Chocolate Box Last Minute Hotel Deals

Hampton Inn & Suites Chicago-North Shore/Skokie

Hampton Inn & Suites Chicago-North Shore/Skokie

3 out of 5
5201 Old Orchard Road Skokie IL
Book a stay at this golf hotel in Skokie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hampton Inn & Suites Chicago-North Shore/Skokie
Residence Inn by Marriott Chicago Wilmette/Skokie

Residence Inn by Marriott Chicago Wilmette/Skokie

3 out of 5
3205 Old Glenview Rd Wilmette IL
Book a stay at this business-friendly hotel in Wilmette. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Residence Inn by Marriott Chicago Wilmette/Skokie
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
9599 Skokie Blvd Skokie IL
Book a stay at this business-friendly hotel in Skokie. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
DoubleTree by Hilton Chicago - North Shore Conference Center
Extended Stay America Suites Chicago Skokie

Extended Stay America Suites Chicago Skokie

2.5 out of 5
5211 Old Orchard Rd Skokie IL
Stay at this hotel in Skokie. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Popular attractions Adagio Teas and North Shore Center for the Performing ...
Extended Stay America Suites Chicago Skokie
Sleek and Cozy 1BR Apartment - Hartrey G

Sleek and Cozy 1BR Apartment - Hartrey G

3.5 out of 5
2533 Hartrey Ave Evanston IL
Stay at this apartment in Evanston. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Welsh-Ryan Arena and Baha'i House of ...
Sleek and Cozy 1BR Apartment - Hartrey G
Renaissance Chicago North Shore Hotel

Renaissance Chicago North Shore Hotel

4 out of 5
933 Skokie Blvd Northbrook IL
Book a stay at this golf hotel in Northbrook. Enjoy free parking, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Renaissance Chicago North Shore Hotel
Sheraton Chicago Northbrook Hotel

Sheraton Chicago Northbrook Hotel

3.5 out of 5
1110 Willow Rd Northbrook IL
Book a stay at this business-friendly hotel in Northbrook. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff ...
Sheraton Chicago Northbrook Hotel
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
1501 Sherman Ave Evanston IL
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
Holiday Inn Chicago North-Evanston by IHG
See all 1,191 properties in Chocolate Box
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.