Search Deals onChocolate Box Vacation Packages
Chocolate Box Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this eco-certified 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 Michigan Avenue are located nearby.
Pendry Chicago
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Courtyard by Marriott Chicago Magnificent Mile
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 3-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 Michigan Avenue and Chicago Riverwalk are located nearby.
Fairmont Chicago at Millennium Park
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this spa 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 Michigan Avenue are located nearby.
Waldorf Astoria Chicago
Save 100% on your flight
per person
Apr 29 - May 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star 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.
Kinzie Hotel
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Emily Hotel
Save 100% on your flight
per person
May 9 - May 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
21c Museum Hotel Chicago
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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 Michigan Avenue and Chicago Riverwalk are located nearby.
The Chicago Hotel Collection - Wrigleyville
Save 100% on your flight
per person
May 7 - May 11
just found
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Hilton Chicago
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field 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
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 ...
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. ...
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 ...
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 Mitchell ...
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 ...
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 ...
Sheraton Chicago Northbrook Hotel
1110 Willow Rd, Northbrook, IL
Stay at this 3.5-star business-friendly hotel in Northbrook. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in ...
Hilton Garden Inn Chicago North Shore/Evanston
1818 Maple Ave, Evanston, IL
Stay at this 3.5-star 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.
Discover Other Travel Deals
- Legoland Florida
- Universal Studios Hollywood®
- Legoland California
- Broadway New York
- The Wizarding World of Harry Potter
- Sanibel Captiva Island
- Paseo de España
- Universal Studios Florida
- San Antonio SeaWorld
- Siargao Island
- Australia Zoo
- Busch Gardens Tampa Bay
- SeaWorld® Orlando
- Tolantongo Caves
- Eleuthera and Harbour Island
- Biltmore Estate
- Blue Lagoon
- Swiss Alps
- Silver Dollar City
- Lackland Air Force Base
- Grand Teton National Park
- San Diego Zoo
- Holy Land Experience
- Grand Ole Opry
- Ark Encounter
- Levi's Stadium
- Breckenridge Ski Resort
- Alcatraz Island
- Six Flags Magic Mountain
- Walt Disney World®
- Dollywood
- Kalahari Waterpark Resort
- Giza Pyramid Complex
- Casino at Don Laughlin's Riverside Resort
- Hoover Dam
- Hollywood Beach
- Faisalabad Clock Tower
- Venice Beach Boardwalk
- Blue Lagoon Beach
- Moraine Lake
- Family Hotels in Chicago
- Hotels with Free Parking in Chicago
- Hotels with a Pool in Chicago
- Apartment Hotel in Chicago
- Luxury Hotels in Chicago
- Hotel Wedding Venues in Chicago
- Historic Hotels in Chicago
- Pet-friendly Hotels in Chicago
- Hotels with an Indoor Pool in Chicago
- Hotels with Hot Tubs in Chicago
Hotels Near Points of Interest in Chocolate Box
- Hotels near Wrigley Field
- Hotels near Lake Michigan
- Hotels near Northwestern University
- Hotels near Donald E. Stephens Convention Center
- Hotels near Allstate Arena
- Hotels near Loyola University Chicago
- Hotels near Rosemont Theatre
- Hotels near Rivers Casino
- Hotels near Aragon Ballroom
- Hotels near Fashion Outlets of Chicago
- Hotels near Chicago Botanic Garden
- Hotels near Copernicus Center
- Hotels near Lincoln Park
- Hotels near Riviera Theatre
- Hotels near Lake Forest College
- Hotels near Vic Theatre
Car Rentals in Chocolate Box
- Car rentals in Schaumburg
- Car rentals in Rosemont
- Car rentals in Evanston
- Car rentals in Skokie
- Car rentals in Arlington Heights
- Car rentals in Schiller Park
- Car rentals in Des Plaines
- Car rentals in Elk Grove Village
- Car rentals in Waukegan
- Car rentals in Oak Park
- Car rentals in Glenview
- Car rentals in Hoffman Estates
- Car rentals in Deerfield
- Car rentals in Northbrook
- Car rentals in Elmhurst
- Car rentals in Villa Park