Hotels Near
Sleepy Hollow

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Featured Sleepy Hollow Hotels

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
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 ...
8.6/10 Excellent! (3,810 reviews)
"Very nice clean 👌 super fancy"

Reviewed on Feb 23, 2025

River Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
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 ...
7.8/10 Good! (8,522 reviews)
"GOOD: beautiful historic hotel with large rooms and bathrooms, good area, good front desk service. BAD - We stayed Fri - Mon. When we came back late in the afternoon, the room was not cleaned, beds were not made both days. Long corridors' and doors' paint is peeling. No curtain rods."

Reviewed on Feb 21, 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
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 ...
9.6/10 Exceptional! (1,691 reviews)
"When we arrived we were greeted by two of the most friendly welcoming people at the desk. They got us our room key and arranged the valet with no issues. We asked a lot of questions about Chicago and transportation and they were more than happy to help us. AMAZiNG!!!!!!"

Reviewed on Feb 24, 2025

L7 Chicago by LOTTE
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
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. ...
8.2/10 Very Good! (2,971 reviews)
"Well maintained. Quiet and clean. Walking distance to the river walk as well as shopping."

Reviewed on Feb 20, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,662 reviews)
"The history"

Reviewed on Feb 21, 2025

Hilton Chicago
Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,308 reviews)
"Good location. Shuttle service from and to airport works perfectly."

Reviewed on Feb 21, 2025

Hyatt Regency O'Hare Chicago
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (3,207 reviews)
"We enjoy our weekend her we will definitely be back"

Reviewed on Feb 19, 2025

Hyatt Regency Chicago
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
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 ...
9.2/10 Wonderful! (2,706 reviews)
"Great area and so much to do!"

Reviewed on Feb 23, 2025

citizenM Chicago Downtown
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
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 ...
8.4/10 Very Good! (1,635 reviews)
"Muy buena atención excelente servicio"

Reviewed on Feb 21, 2025

Fairmont Chicago at Millennium Park
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4 out of 5
150 East Ontario Street, Chicago, IL
Fully refundableReserve now, pay when you stay
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Millennium Park are located nearby.
9.2/10 Wonderful! (1,480 reviews)
"Great!"

Reviewed on Feb 20, 2025

Hotel Riu Plaza Chicago
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundable
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (3,392 reviews)
"This is a recommendable stay for any reason in Chicago"

Reviewed on Feb 21, 2025

Club Quarters Hotel, Central Loop, Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
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 ...
8.6/10 Excellent! (1,001 reviews)
"Just a quick stop over. The location was perfect and very friendly front desk staff"

Reviewed on Feb 17, 2025

The Westin Michigan Avenue Chicago
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.

Hotels in Sleepy Hollow

Chicago is a city that has a lot going on, but you have your sights set on Sleepy Hollow. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Sleepy Hollow has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Sleepy Hollow hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Chicago so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Sleepy Hollow underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Sleepy Hollow city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Sleepy Hollow cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Sleepy Hollow at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $113
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Sleepy Hollow hotel you want, book it, and never look back. Because your great escape is ahead of you.