Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was $587, price is now $442 per person
$442
per person
Apr 8 - Apr 12
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa 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.
La Banque Hotel
Price was $1,008, price is now $763 per person
$763
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $856, price is now $511 per person
$511
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Greensboro (GSO) 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.
The Wade
Downtown Chicago
Save 100% on your flight
Price was $963, price is now $693 per person
$693
per person
Apr 14 - Apr 20
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $770, price is now $555 per person
$555
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Greensboro (GSO) 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.
Aloft Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
Price was $685, price is now $501 per person
$501
per person
Mar 31 - Apr 4
found 3 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $797, price is now $600 per person
$600
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Greensboro (GSO) 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $884, price is now $669 per person
$669
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Greensboro (GSO) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
3-4 Night Vacations in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Sleepy Hollow
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
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 ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
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 ...
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
Save an average of 15% on thousands of hotels when you're signed in
Hilton Chicago
720 S Michigan Ave Chicago IL
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 ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool 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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$88 Roundtrip, just found
$88
Roundtrip
just found
Thu, Apr 9 - Tue, Apr 14
LAX
Los Angeles Intl.
MDW
Midway Intl.
$192 Roundtrip, found 2 hours ago
$192
Roundtrip
found 2 hours ago
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$242 Roundtrip, found 5 days ago
$242
Roundtrip
found 5 days ago
Tue, Mar 3 - Tue, Mar 17
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,064 Roundtrip, found 2 days ago
$1,064
Roundtrip
found 2 days ago
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