Hotels in Sleepy Hollow
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Featured Hotels in Sleepy Hollow

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.22 mi from Sleepy Hollow
$119 nightly
The price is $141 total per night
$141 total
Dec 3 - Dec 4
Total with taxes and fees
At THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel, guests have access to a 24-hour gym, free WiFi in public areas, and conference space. Multilingual staff at the 24-hour front desk can assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.
Pet friendly
Free WiFi

Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.26 mi from Sleepy Hollow
$160 nightly
The price is $190 total per night
$190 total
Nov 22 - Nov 23
Total with taxes and fees
Guests staying at Hilton Chicago enjoy an indoor pool, a gym, and a sauna. Valet parking is offered for USD 88.00 per day. The 24-hour front desk has multilingual staff ready to assist with luggage storage, dry cleaning/laundry, and securing valuables. Other amenities at this historic hotel include free WiFi in public areas, a hot tub, and a conference center.
Pool
Hot Tub

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.39 mi from Sleepy Hollow
$106 nightly
The price is $126 total per night
$126 total
Nov 22 - Nov 23
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant

The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.86 mi from Sleepy Hollow
$156 nightly
The price is $185 total per night
$185 total
Dec 9 - Dec 10
Total with taxes and fees
The Royal Sonesta Chicago Downtown offers a 24-hour gym, conference space, and a business center. Valet parking is available for USD 80 per night. The front desk has multilingual staff standing by 24 hours a day to assist with tours/tickets and luggage storage. Additional amenities include wedding services, an ATM, and a ballroom.
Pet friendly
Free WiFi

River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.87 mi from Sleepy Hollow
$106 nightly
The price is $126 total per night
$126 total
Dec 10 - Dec 11
Total with taxes and fees
River Hotel features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 76 per night. The front desk is staffed 24/7 to help with concierge services, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a business center, and express check-in.
Pet friendly
Free WiFi

Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.98 mi from Sleepy Hollow
$229 nightly
The price is $272 total per night
$272 total
Nov 24 - Nov 25
Total with taxes and fees
Guests staying at Fairmont Chicago at Millennium Park enjoy access to a full-service spa, a 24-hour gym, and free WiFi in public areas. Parking is available for USD 38 per day (USD 88 per day for valet parking), and there's also limo/town car service. The 24-hour front desk has staff standing by to help with tours or tickets, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include meeting rooms, conference space, and a business center.
Spa
Pet friendly

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
8.36 mi from Sleepy Hollow
$116 nightly
The price is $138 total per night
$138 total
Nov 23 - Nov 24
Total with taxes and fees
The Chicago Hotel Collection - Magnificent Mile offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is offered for USD 92.44 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Other amenities at this boutique hotel include meeting rooms, coffee/tea in a common area, and express check-out.
Pet friendly
Free WiFi

The Wade
644 N Lake Shore Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
8.55 mi from Sleepy Hollow
$119 nightly
The price is $141 total per night
$141 total
Nov 23 - Nov 24
Total with taxes and fees
At The Wade, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Valet parking is offered for USD 86 per night. The 24-hour front desk has staff standing by to help with tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this luxury hotel include conference space, a 24-hour business center, and express check-out.
Pool
Pet friendly

The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
8.66 mi from Sleepy Hollow
$116 nightly
The price is $138 total per night
$138 total
Nov 11 - Nov 12
Total with taxes and fees
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 82 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, and a reception hall.
Pet friendly
Free WiFi
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.
Sleepy Hollow hotels essential information
Accommodation | 4,668 hotels |
|---|---|
Lowest Price | $126 |
Highest Price | $272 |
Popular hotels | Congress Plaza Hotel, The Chicago Hotel Collection Ambassador Gold Coast, River Hotel, The Wade, The Chicago Hotel Collection - Magnificent Mile, Hilton Chicago, THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel, The Royal Sonesta Chicago Downtown, Fairmont Chicago at Millennium Park |
Recent Reviews

The Chicago Hotel Collection - Magnificent Mile
5/5 Excellent
"Loved the room"
A verified traveler stayed at The Chicago Hotel Collection - Magnificent Mile
Posted less than an hour ago
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