Sleepy Hollow Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was $878, price is now $654 per person
$654
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.
AC in rooms work but not much control it’s very regulated. No microwave. And shower to bathtub. New nice big rooms
Reviewed on Jul 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,137, price is now $1,415 per person
$1,415
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Phoenix (PHX) 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 restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Hotel was nice and close to the amenities of the pier. Only downside was most attractions are in the city which makes this location not as ideal.
Reviewed on Jul 22, 2026
Villa Christina
Greater Grand Crossing
Save 100% on your flight
Price was $1,102, price is now $757 per person
$757
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Griffin Museum of Science and Industry and Rate Field are located nearby.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $2,252, price is now $1,552 per person
$1,552
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Everything was great!
Reviewed on Jul 22, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $2,464, price is now $1,704 per person
$1,704
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this 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.
Sports Illustrated Resorts Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,982, price is now $1,467 per person
$1,467
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Would not recommend. My room smelled like mold the entire time I was there. The bathroom also felt very unsafe—the shower is level with the tile floor, so water gets all over the bathroom, making it extremely slippery. I ended up staying for only about 5 hours but was still charged for two nights. Overall, a very disappointing experience.
Reviewed on Jul 22, 2026
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See all available trips from Columbus to Sleepy Hollow
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DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
28.5 km from city center
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
DoubleTree by Hilton Chicago - Arlington Heights
75 W Algonquin Rd Arlington Heights IL
26.52 km from city center
Book a stay at this business-friendly hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
26.5 km from city center
Book a stay at this spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
The Westin Chicago Northwest
400 Park Blvd Itasca IL
26.16 km from city center
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the ...
Hyatt Place Itasca
1150 North Arlington Heights Road Itasca IL
27.22 km from city center
Book a stay at this business-friendly hotel in Itasca. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
29.37 km from city center
Book a stay at this business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
22.07 km from city center
Stay at this motel in Rolling Meadows. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Sheraton Suites Chicago Elk Grove
121 Northwest Point Boulevard Elk Grove Village IL
27.05 km from city center
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Woodfield Mall ...
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd Schaumburg IL
22.48 km from city center
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Country Inn & Suites by Radisson, Schaumburg, IL
1401 North Roselle Road Schaumburg IL
18.79 km from city center
Book a stay at this family-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
22 West Algonquin Road Arlington Heights IL
26.62 km from city center
Stay at this hotel in Arlington Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Woodfield Mall and Schaumburg Medieval ...
Hyatt Place Chicago/ Schaumburg
1851 McConnor Parkway Schaumburg IL
22.56 km from city center
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Country Inn & Suites by Radisson, Elk Grove Village/Itasca
1160 W Devon Avenue Elk Grove Village IL
25.07 km from city center
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Aug 27 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$194 Roundtrip, found 4 days ago
$194
Roundtrip
found 4 days ago
Thu, Sep 17 - Mon, Sep 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Tue, Sep 15 - Tue, Sep 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Mon, Sep 28 - Fri, Oct 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 6 hours ago
$247
Roundtrip
found 6 hours ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$297 Roundtrip, found 7 hours ago
$297
Roundtrip
found 7 hours ago