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.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was $405, price is now $296 per person
$296
per person
Dec 12 - Dec 16
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $762, price is now $521 per person
$521
per person
Dec 12 - Dec 16
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $670, price is now $485 per person
$485
per person
Dec 12 - Dec 16
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $560, price is now $407 per person
$407
per person
Dec 12 - Dec 16
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $375 per person
$375
per person
Dec 12 - Dec 16
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
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. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Residence Inn by Marriott Chicago Downtown / River North
Downtown Chicago
Save 100% on your flight
Price was $478, price is now $350 per person
$350
per person
Dec 12 - Dec 16
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
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DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd, Wood Dale, IL
28.66 km from city center
Stay at this 4-star business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Eaglewood Resort and Spa
1401 Nordic Rd, Itasca, IL
26.53 km from city center
Stay at this 4-star 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 ...
Motel 6 Elk Grove Village, IL
1000 W Devon Ave, Elk Grove Village, IL
25.41 km from city center
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
Comfort Inn & Suites Arlington Heights - Buffalo Grove
3700 N Wilke Rd, Arlington Heights, IL
24.72 km from city center
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd, Schaumburg, IL
21.74 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 clean rooms in our reviews. ...
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road, Schaumburg, IL
22 km from city center
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and a free area shuttle. Our guests praise the helpful staff and the ...
Holiday Inn Express Chicago NW - Arlington Heights by IHG
2111 S Arlington Heights Rd, Arlington Heights, IL
26.74 km from city center
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Courtyard by Marriott Chicago Wood Dale
900 N Wood Dale Rd, Wood Dale, IL
29.3 km from city center
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
DoubleTree by Hilton Chicago - Arlington Heights
75 W Algonquin Rd, Arlington Heights, IL
26.48 km from city center
Stay at this 4-star business-friendly hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd, Arlington Heights, IL
26.67 km from city center
Stay at this 3-star business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Chez Hotel Arlington Heights
519 W Algonquin Rd, Arlington Heights, IL
26.12 km from city center
Stay at this 4-star hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83, Mundelein, IL
29.37 km from city center
Stay at this 4-star business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Country Inn & Suites by Radisson, Elk Grove Village/Itasca
1160 W Devon Avenue, Elk Grove Village, IL
25.07 km from city center
Stay at this 3-star 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.
Tue, Dec 23 - Tue, Dec 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Thu, Nov 13 - Sat, Nov 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$245 Roundtrip, found 2 days ago
$245
Roundtrip
found 2 days ago
Tue, Mar 17 - Tue, Mar 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Fri, Mar 20 - Wed, Mar 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago
Fri, Mar 20 - Wed, Mar 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$379 Roundtrip, found 1 day ago
$379
Roundtrip
found 1 day ago