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Chocolate Box Vacation Packages

Chocolate Box Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 out of 5
Price was $493, price is now $377 per person
$377
per person
Mar 12 - Mar 16
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this aparthotel in Chicago. Enjoy a fitness center, concierge services, and premium bedding. Our guests praise the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,254, price is now $830 per person
$830
per person
Mar 13 - Mar 17
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $781, price is now $530 per person
$530
per person
Mar 17 - Mar 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $938, price is now $650 per person
$650
per person
Mar 13 - Mar 17
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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,455, price is now $1,035 per person
$1,035
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $757, price is now $575 per person
$575
per person
Mar 17 - Mar 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 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.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,063, price is now $808 per person
$808
per person
Mar 14 - Mar 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, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was $721, price is now $551 per person
$551
per person
Mar 17 - Mar 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.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Price was $600, price is now $459 per person
$459
per person
Mar 17 - Mar 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $571, price is now $438 per person
$438
per person
Mar 8 - Mar 12
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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $773, price is now $594 per person
$594
per person
Mar 17 - Mar 21
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.
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Price was $629, price is now $485 per person
$485
per person
Mar 17 - Mar 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 breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

3-4 Night Vacations in Chocolate Box

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $351, price is now $255 per person
$255
per person
Mar 6 - Mar 9
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 $513, price is now $326 per person
$326
per person
Mar 6 - Mar 9
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
Price was $1,017, price is now $704 per person
$704
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $938, price is now $650 per person
$650
per person
Mar 13 - Mar 17
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,386, price is now $709 per person
$709
per person
Mar 14 - Mar 21
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
Price was $2,179, price is now $1,175 per person
$1,175
per person
Mar 14 - Mar 21
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 $1,404, price is now $858 per person
$858
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,296, price is now $820 per person
$820
per person
Mar 14 - Mar 21
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.