Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Chicago-Vernon Hills by IHG
per person
Jul 2 - Jul 7
found 6 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Vernon Hills. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Cuneo Mansion and Gardens and Conway Farms Golf Club are located nearby.
Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
per person
Jul 20 - Jul 25
just found
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clark Street Beach and Halim Time & Glass Museum are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 5-star 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.
DayDreamer Domes
Save 100% on your flight
per person
Jul 13 - Jul 19
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star hotel in South Haven. Enjoy free parking, room service, and onsite spa services. Popular attractions Kal Haven Trail and Michigan Maritime Museum are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 14
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Holiday Inn Chicago - Schaumburg by IHG
per person
Jul 2 - Jul 7
found 6 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Woodfield Mall and Schaumburg Medieval Times are located nearby.
Hyatt Regency O'Hare Chicago
O'Hare
Save 100% on your flight
per person
Jun 28 - Jul 4
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rosemont Theatre 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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Save an average of 15% on thousands of hotels when you're signed in
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
River Hotel
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 ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
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 ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
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.
Tue, Jul 22 - Wed, Jul 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 2 hours ago
$110
Roundtrip
found 2 hours ago
Sat, Jun 7 - Mon, Jun 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Sat, Jul 12 - Wed, Jul 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$248 Roundtrip, found 4 hours ago
$248
Roundtrip
found 4 hours ago
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$889 Roundtrip, found 2 days ago
$889
Roundtrip
found 2 days ago
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