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

Motel 6 - Chicago, IL
Price was $303, price is now $225 per person
$225
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located nearby.

Courtyard by Marriott Chicago Schaumburg/Woodfield Mall
Price was $522, price is now $372 per person
$372
per person
Nov 25 - Dec 2
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.

Holiday Inn Chicago-Oakbrook by IHG
Price was $346, price is now $247 per person
$247
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Villa Park. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Drury Lane Theater are located nearby.

Holiday Inn Chicago - Schaumburg by IHG
Price was $406, price is now $291 per person
$291
per person
Nov 28 - Dec 3
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 our reviews. Popular attractions Woodfield Mall and Schaumburg Medieval Times are located nearby.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $923, price is now $524 per person
$524
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Viceroy Chicago
Save 100% on your flight
Price was $1,429, price is now $848 per person
$848
per person
Nov 25 - Dec 2
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.

theWit Chicago, a Hilton Hotel
Save 100% on your flight
Price was $857, price is now $512 per person
$512
per person
Nov 23 - Nov 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury 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 Chicago Riverwalk and Millennium Park are located nearby.

Thompson Chicago, by Hyatt
Save 100% on your flight
Price was $1,060, price is now $672 per person
$672
per person
Nov 25 - Dec 2
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago Fulton Market
Save 100% on your flight
Price was $857, price is now $548 per person
$548
per person
Nov 23 - Nov 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $797, price is now $513 per person
$513
per person
Dec 4 - Dec 8
found 8 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,732, price is now $1,125 per person
$1,125
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 5-star 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.

Sofitel Chicago Magnificent Mile
Save 100% on your flight
Price was $583, price is now $390 per person
$390
per person
Dec 10 - Dec 15
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. 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

Hampton Inn & Suites Chicago-North Shore/Skokie
5201 Old Orchard Road, Skokie, IL
Stay at this 3-star golf hotel in Skokie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

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 ...

Renaissance Chicago North Shore Hotel
933 Skokie Blvd, Northbrook, IL
Stay at this 4-star 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
Stay at this 3-star business-friendly hotel in Wilmette. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

DoubleTree by Hilton Chicago - North Shore Conference Center
9599 Skokie Blvd, Skokie, IL
Stay at this 4-star business-friendly hotel in Skokie. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...

Sleek and Cozy 1BR Apartment - Hartrey G
2533 Hartrey Ave, Evanston, IL
Stay at this 3.5-star apartment in Evanston. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Welsh-Ryan Arena and Ryan Field ...

Sheraton Chicago Northbrook Hotel
1110 Willow Rd, Northbrook, IL
Stay at this 3.5-star 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
Stay at this 3-star business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
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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