Hotels Near
Sleepy Hollow

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Featured Sleepy Hollow Hotels

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
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 ...
7.8/10 Good! (8,797 reviews)
"Great experience overall. Rooms were “modern” compared to beautiful lobby and building. Rooms ad beautiful view of Millenium park."

Reviewed on May 11, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
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 ...
8.8/10 Excellent! (2,206 reviews)
"Lobby employees are fantastic"

Reviewed on May 11, 2025

Hilton Chicago/Magnificent Mile Suites
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
8/10 Very Good! (2,856 reviews)
"Love it !"

Reviewed on May 12, 2025

Warwick Allerton - 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! (1,008 reviews)
"We had classes at the John Hancock Center. This hotel was directly across the street! The staff were nice. Dining was a little confusing as there is one entrance for breakfast and a different entrance for the same restaurant for dinner. I would definitely stay here again!"

Reviewed on May 11, 2025

The Westin Michigan Avenue Chicago
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! (4,141 reviews)
"All around excellent"

Reviewed on May 10, 2025

River Hotel
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! (1,722 reviews)
"Staff friendly, great location, and large rooms. Would stay again."

Reviewed on May 10, 2025

Fairmont Chicago at Millennium Park
Holiday Inn Chicago Dwtn - The Mart by IHG
Holiday Inn Chicago Dwtn - The Mart by IHG
3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,579 reviews)
"The view was beautiful"

Reviewed on May 11, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
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. ...
8.2/10 Very Good! (4,039 reviews)
"We had a great time! The only thing that bothered us was the noise by our room door. My daughter couldn't sleep with the noise of the doors opening and closing."

Reviewed on May 12, 2025

Embassy Suites by Hilton Chicago Downtown River North
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! (3,041 reviews)
"really clean, really nice building, and location. Really good price points at certain dates. Far better (newer and well-maintained) than hotels nearby."

Reviewed on May 12, 2025

citizenM Chicago Downtown
Freehand Chicago
Freehand Chicago
4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
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. ...
7.8/10 Good! (1,788 reviews)
"Everything you need for a solo travel it’s neat and tidy."

Reviewed on May 11, 2025

Freehand Chicago
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,665 reviews)
"Always a good time"

Reviewed on May 13, 2025

Hotel Felix River North/Magnificent Mile
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,015 reviews)
"Comfy rooms and friendly, professional staff."

Reviewed on May 9, 2025

Crowne Plaza Chicago West Loop by IHG
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
  • 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.