Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago-Oakbrook by IHG
Price was $346, price is now $247 per person
$247
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Villa Park. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Drury Lane Theater are located nearby.
Courtyard by Marriott Chicago Schaumburg/Woodfield Mall
Price was $522, price is now $372 per person
$372
per person
Nov 25 - Dec 2
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $923, price is now $524 per person
$524
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Viceroy Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,429, price is now $848 per person
$848
per person
Nov 25 - Dec 2
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $857, price is now $512 per person
$512
per person
Nov 23 - Nov 29
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury 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 Chicago Riverwalk and Millennium Park are located nearby.
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $1,060, price is now $672 per person
$672
per person
Nov 25 - Dec 2
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $857, price is now $548 per person
$548
per person
Nov 23 - Nov 29
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $797, price is now $513 per person
$513
per person
Dec 4 - Dec 8
found 7 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, 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 The Dome at the Parkway Bank Sports Complex 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 ...
Freehand Chicago
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
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 ...
Embassy Suites by Hilton Chicago Downtown River North
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. ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Fri, Nov 7 - Tue, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago
Sat, Nov 8 - Mon, Nov 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago
Thu, Oct 23 - Sun, Oct 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Wed, Nov 5 - Mon, Dec 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$999 Roundtrip, found 3 days ago
$999
Roundtrip
found 3 days ago
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