Sleepy Hollow Vacations
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Sleepy Hollow 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 1 day 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 1 day 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.
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,222, price is now $893 per person
$893
per person
Dec 24 - Dec 29
found 1 day 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.
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Reviewed on Nov 10, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
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 1 day 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.
Everything very nice it is centered where u can go to a lot of attractions
Reviewed on Nov 10, 2026
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
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.
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
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DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
28.5 km from city center
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd Schaumburg IL
21.71 km from city center
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
26.65 km from city center
Book a stay at this business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
22.07 km from city center
Stay at this motel in Rolling Meadows. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Hyatt Place Itasca
1150 North Arlington Heights Road Itasca IL
27.22 km from city center
Book a stay at this business-friendly hotel in Itasca. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
22.6 km from city center
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Chez Hotel Arlington Heights
519 W Algonquin Rd Arlington Heights IL
26.12 km from city center
Stay at this hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Geneva Motel Inn
100 South Tyler Rd St. Charles IL
20.11 km from city center
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Country Inn & Suites by Radisson, Schaumburg, IL
1401 North Roselle Road Schaumburg IL
18.79 km from city center
Book a stay at this family-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Motel 6 Arlington Heights, IL - Chicago North Central
441 W Algonquin Rd Arlington Heights IL
26.27 km from city center
Stay at this motel in Arlington Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
26.5 km from city center
Book a stay at this spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
The Westin Chicago Northwest
400 Park Blvd Itasca IL
26.16 km from city center
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
29.37 km from city center
Book a stay at this business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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.