Search Deals on
Sleepy Hollow Vacation Packages

3-4 Night Vacations in Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
Chatham
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
per person
May 13 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cheap Hotel Deals in Sleepy Hollow

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Crowne Plaza Chicago West Loop by IHG
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
Swissotel - Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Embassy Suites by Hilton Chicago Downtown River North
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
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 ...
Hilton Chicago/Magnificent Mile Suites
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave, Chicago, IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
L7 Chicago by LOTTE
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
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.

Spirit Airlines
Wed, Apr 23 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Apr 23 from Los Angeles Intl. to O'Hare Intl., returning Sat, Apr 26, priced at $124 found 5 days ago
Frontier Airlines
Sat, Jun 21 - Wed, Jun 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 1 day ago
$208
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 21 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 25, priced at $208 found 1 day ago
Alaska Airlines
Tue, Apr 29 - Wed, May 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 1 hour ago
$218
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Tue, Apr 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 7, priced at $218 found 1 hour ago
Frontier Airlines
Sat, Apr 19 - Wed, Apr 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$253 Roundtrip, found 5 days ago
$253
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Apr 19 from Los Angeles Intl. to Midway Intl., returning Wed, Apr 23, priced at $253 found 5 days ago