Search Deals onIllinois Vacation Packages
Illinois Flight + Hotel packages
Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Save 100% on your flight
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for Hyatt Place Chicago/Downtown - The Loop, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
21c Museum Hotel Chicago
Downtown Chicago
Save 100% on your flight
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for 21c Museum Hotel Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for The Langham, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy WiFi, a fitness center, and valet parking. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for Staypineapple, An Iconic Hotel, The Loop, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for Eurostars Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Hilton Garden Inn Chicago Downtown Riverwalk
Downtown Chicago
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for Hilton Garden Inn Chicago Downtown Riverwalk, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast, and onsite parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for The Whitehall Hotel, BW Premier Collection, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Dec 29 - Jan 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Navy Pier and Wrigley Field are located nearby. Discover genuine guest reviews for Pendry Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.
3-4 Night Vacations in Illinois
Prices and availability subject to change. Additional terms may apply.
Cheap Hotel Deals in Illinois
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
