Search Deals onChocolate Box Vacation Packages
Chocolate Box Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
Save 100% on your flight
Price was $608, price is now $404 per person
$404
per person
Jul 25 - Jul 29
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,372, price is now $862 per person
$862
per person
Jul 15 - Jul 19
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.
Swissotel - Chicago
Save 100% on your flight
Price was $1,448, price is now $926 per person
$926
per person
Jul 15 - Jul 19
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.
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,296, price is now $833 per person
$833
per person
Jul 15 - Jul 19
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.
Thompson Chicago, by Hyatt
Save 100% on your flight
Price was $1,707, price is now $1,140 per person
$1,140
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,388, price is now $928 per person
$928
per person
Jul 15 - Jul 19
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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
Price was $1,388, price is now $928 per person
$928
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, 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
Save 100% on your flight
Price was $1,401, price is now $945 per person
$945
per person
Jul 15 - Jul 19
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.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $1,146, price is now $777 per person
$777
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 55 Chicago Downtown
Save 100% on your flight
Price was $1,251, price is now $853 per person
$853
per person
Jul 27 - Aug 1
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 Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Save 100% on your flight
Price was $1,343, price is now $917 per person
$917
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Viceroy Chicago
Save 100% on your flight
Price was $1,659, price is now $1,141 per person
$1,141
per person
Jul 23 - Jul 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, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue 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
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 ...
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 ...
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 ...
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 ...
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 ...
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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