Willow Springs Vacations
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Willow Springs Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Blackstone, Autograph Collection
Downtown Chicago
Price was $968, price is now $765 per person
$765
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,375, price is now $939 per person
$939
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) 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.
Price to high for the quality.
Reviewed on Nov 9, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,222, price is now $893 per person
$893
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,942, price is now $1,430 per person
$1,430
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) 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.
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨
Reviewed on Nov 9, 2026
Swissotel - Chicago
Downtown Chicago
Price was $1,165, price is now $882 per person
$882
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) 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.
Park Hyatt Chicago
Downtown Chicago
Price was $1,972, price is now $1,547 per person
$1,547
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
24.55 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
26.53 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
River Hotel
75 East Wacker Drive Chicago IL
25.34 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Wade
644 N Lake Shore Dr Chicago IL
26.43 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
26.11 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Hilton Chicago
720 S Michigan Ave Chicago IL
24.33 km from city center
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
24.29 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
25.32 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
25.51 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Eurostars Magnificent Mile
660 North State Street Chicago IL
25.64 km from city center
Book a stay at this 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 ...
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
25.23 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
The Godfrey Hotel Chicago
127 West Huron, at LaSalle Chicago IL
25.45 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Freehand Chicago
19 East Ohio Street Chicago IL
25.56 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.