Search Deals onChocolate Box Vacation Packages
Chocolate Box Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

La Banque Hotel
Price was $744, price is now $544 per person
$544
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.

Swissotel - Chicago
Save 100% on your flight
Price was $1,830, price is now $1,006 per person
$1,006
per person
Jun 18 - Jun 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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.

The Wade
Save 100% on your flight
Price was $1,810, price is now $1,049 per person
$1,049
per person
Jun 17 - Jun 23
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.

Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,576, price is now $1,013 per person
$1,013
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,065, price is now $709 per person
$709
per person
Jul 2 - Jul 6
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.

Eurostars Magnificent Mile
Save 100% on your flight
Price was $1,515, price is now $1,015 per person
$1,015
per person
Jun 18 - Jun 24
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 a 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.

Level Chicago Fulton Market
Save 100% on your flight
Price was $950, price is now $655 per person
$655
per person
Jul 2 - Jul 6
found 1 day 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.

Pendry Chicago
Save 100% on your flight
Price was $1,340, price is now $930 per person
$930
per person
Jun 25 - Jun 29
found 18 hours 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.

Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $1,401, price is now $1,015 per person
$1,015
per person
Jun 18 - Jun 23
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 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.

Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,829, price is now $1,328 per person
$1,328
per person
Jun 17 - Jun 21
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.

LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $826, price is now $602 per person
$602
per person
Jul 2 - Jul 6
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.

The Emily Hotel
Save 100% on your flight
Price was $1,337, price is now $985 per person
$985
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 United Center and Chicago Riverwalk are located nearby.
3-4 Night Vacations in Chocolate Box
Price found within the past 48 hours. Click for updated prices.



5-7 Night Vacations in Chocolate Box
Price found within the past 48 hours. Click for updated prices.



Chocolate Box Last Minute Hotel Deals

Hampton Inn & Suites Chicago-North Shore/Skokie
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. ...

DoubleTree by Hilton Chicago - North Shore Conference Center
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 ...

Renaissance Chicago North Shore Hotel
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 ...

Residence Inn by Marriott Chicago Wilmette/Skokie
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 ...

Extended Stay America Suites Chicago Skokie
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 North Shore Center for the Performing Arts and Wagner ...

Holiday Inn Chicago North-Evanston by IHG
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 ...

Sheraton Chicago Northbrook Hotel
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 ...

Hilton Garden Inn Chicago North Shore/Evanston
1818 Maple Ave Evanston IL
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff ...
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.
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