Sleepy Hollow Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,083, price is now $771 per person
$771
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,383, price is now $917 per person
$917
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,328, price is now $888 per person
$888
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,178, price is now $826 per person
$826
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
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 in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $856 per person
$856
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,198, price is now $878 per person
$878
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
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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 ...
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 ...
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 ...
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 ...
Hyatt Place Chicago/Hoffman Estates
2750 Greenspoint Pkwy Hoffman Estates IL
13.16 km from city center
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
22 West Algonquin Road Arlington Heights IL
26.62 km from city center
Stay at this hotel in Arlington Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Woodfield Mall and Allstate Arena are located ...
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. ...
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
22.04 km from city center
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
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 ...
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 ...
Holiday Inn Express Chicago NW - Arlington Heights by IHG
2111 S Arlington Heights Rd Arlington Heights IL
26.76 km from city center
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Red Lion Inn & Suites Elk Grove Village
1925 E Higgins Rd Elk Grove Village IL
29.49 km from city center
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
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 ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Apr 17 - Tue, Apr 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 3 days ago
$109
Roundtrip
found 3 days ago
Wed, May 6 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Wed, May 6 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Wed, May 6 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$219 Roundtrip, found 2 hours ago
$219
Roundtrip
found 2 hours ago
Wed, May 6 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 2 hours ago
$237
Roundtrip
found 2 hours ago