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Chocolate Box Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Save 100% on your flight
Price was $338, price is now $205 per person
$205
per person
Dec 9 - Dec 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rob Roy Golf Course and Northbrook Sports Complex are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was $2,386, price is now $1,316 per person
$1,316
per person
Nov 28 - Dec 3
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $508, price is now $308 per person
$308
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star golf hotel in Downers Grove. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Morton Arboretum and Yorktown Shopping Center are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $2,234, price is now $1,489 per person
$1,489
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,312, price is now $748 per person
$748
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-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 United Center 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 $502, price is now $292 per person
$292
per person
Dec 7 - Dec 11
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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $916, price is now $556 per person
$556
per person
Dec 9 - Dec 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,462, price is now $907 per person
$907
per person
Nov 21 - Nov 28
found 4 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $551, price is now $346 per person
$346
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $515, price is now $325 per person
$325
per person
Dec 9 - Dec 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Hyatt Centric Chicago Ohare

Hyatt Centric Chicago Ohare

3.5 out of 5
Save 100% on your flight
Price was $538, price is now $344 per person
$344
per person
Dec 9 - Dec 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Rosemont. Enjoy free WiFi, 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 Rivers Casino are located nearby.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $408, price is now $266 per person
$266
per person
Dec 9 - Dec 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.

3-4 Night Vacations in Chocolate Box

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

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $502, price is now $292 per person
$292
per person
Dec 7 - Dec 11
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 $1,123, price is now $659 per person
$659
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $551, price is now $346 per person
$346
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $629, price is now $435 per person
$435
per person
Dec 7 - Dec 11
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.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $508, price is now $308 per person
$308
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $2,386, price is now $1,316 per person
$1,316
per person
Nov 28 - Dec 3
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,841, price is now $844 per person
$844
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,338, price is now $718 per person
$718
per person
Nov 25 - Dec 2
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
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. ...
Hampton Inn & Suites Chicago-North Shore/Skokie
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 North Shore Center for the Performing Arts and Wagner ...
Extended Stay America Suites Chicago 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
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 ...
Residence Inn by Marriott Chicago Wilmette/Skokie
Renaissance Chicago North Shore Hotel

Renaissance Chicago North Shore Hotel

4 out of 5
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 ...
Renaissance Chicago North Shore Hotel
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
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 ...
DoubleTree by Hilton Chicago - North Shore Conference Center
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 3.5-star apartment in Evanston. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Welsh-Ryan Arena and Ryan Field ...
Sleek and Cozy 1BR Apartment - Hartrey G
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
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 ...
Holiday Inn Chicago North-Evanston by IHG
Sheraton Chicago Northbrook Hotel

Sheraton Chicago Northbrook Hotel

3.5 out of 5
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 ...
Sheraton Chicago Northbrook Hotel
See all 1,091 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.

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