Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
La Banque Hotel
Save 100% on your flight
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star 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.
Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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.
Graduate by Hilton Evanston
Downtown Evanston
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Baha'i House of Worship and Aragon Ballroom are located nearby.
Fairmont Chicago at Millennium Park
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)
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 rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
L7 Chicago by LOTTE
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)
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 the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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 ...
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 ...
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
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 ...
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 ...
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
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 ...
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 ...
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.
Mon, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Thu, Jun 5 - Wed, Jun 11
LAX
Los Angeles Intl.
MDW
Midway Intl.
$251 Roundtrip, found 2 days ago
$251
Roundtrip
found 2 days ago
Tue, Aug 26 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$529 Roundtrip, found 18 hours ago
$529
Roundtrip
found 18 hours ago
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$889 Roundtrip, found 3 days ago
$889
Roundtrip
found 3 days ago
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