Search Hotels in Sleepy Hollow, Chicago

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
5 Sept - 6 Sept
Tomorrow
6 Sept - 7 Sept
This weekend
5 Sept - 7 Sept
Next weekend
12 Sept - 14 Sept

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Sleepy Hollow, Chicago

Our top choices for Sleepy Hollow hotels

River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4608)
"Great place to stay, staff was very friendly"
The price is ₹13,928
₹16,350 total
includes taxes & fees
14 Sept - 15 Sept
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2014)
"Overall a nice place to stay."
The price is ₹14,739
₹17,302 total
includes taxes & fees
21 Sept - 22 Sept
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3043)
"Great stay!"
The price is ₹15,994
₹18,776 total
includes taxes & fees
5 Oct - 6 Oct
Eurostars Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2112)
"Great place to stay!"
The price is ₹17,560
₹23,170 total
includes taxes & fees
14 Sept - 15 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3722)
"Great place to stay "
The price is ₹16,783
₹19,702 total
includes taxes & fees
22 Sept - 23 Sept
citizenM Chicago Downtown
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2164)
"Amazing stay and great location…"
The price is ₹16,213
₹21,620 total
includes taxes & fees
14 Sept - 15 Sept
Hilton Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3816)
"Great place to stay "
The price is ₹14,311
₹16,799 total
includes taxes & fees
14 Sept - 15 Sept
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9065)
"Great place to stay! Wonderful staff and ambience and walkable to many things. "
The price is ₹17,401
₹20,427 total
includes taxes & fees
13 Sept - 14 Sept
Congress Plaza Hotel
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2810)
"Close to everything, easy check-in/out and friendly staff!"
The price is ₹13,047
₹15,315 total
includes taxes & fees
14 Sept - 15 Sept
Aloft Chicago Mag Mile
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1026)
"The hotel is a bit outdated but decent. The location is very good, easy access to many good areas around it."
The price is ₹12,663
₹14,865 total
includes taxes & fees
2 Oct - 3 Oct
Best Western River North Hotel
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2288)
"Nice place to stay!"
The price is ₹9,432
₹12,623 total
includes taxes & fees
22 Sept - 23 Sept
Freehand Chicago
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2794)
"Great staff clean rooms and good location"
The price is ₹14,148
₹16,608 total
includes taxes & fees
22 Sept - 23 Sept
Hilton Chicago/Magnificent Mile Suites
Holiday Inn & Suites Chicago - Downtown by IHG
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very good, (1009)
"Staff was very friendly The rooftop pool was really nice. "
The price is ₹14,898
₹18,546 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn & Suites Chicago - Downtown by IHG
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1455)
"Great place to stay. "
The price is ₹17,102
₹20,076 total
includes taxes & fees
28 Sept - 29 Sept
Crowne Plaza Chicago West Loop by IHG
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (225)
"Great place "
The price is ₹10,476
₹12,298 total
includes taxes & fees
24 Sept - 25 Sept
FOUND Hotel Chicago River North
Regal Inn - Chicago O'Hare Airport
Lobby

Regal Inn - Chicago O'Hare Airport

2.0 star property
8.0 out of 10, Very good, (1002)
"Staff was very nice and accommodating. I would definitely stay at the Regal in the future."
Regal Inn - Chicago O'Hare Airport
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2391)
"Enjoyed our stay "
The price is ₹16,508
₹21,861 total
includes taxes & fees
1 Oct - 2 Oct
Hotel Riu Plaza Chicago
The Whitehall Hotel, BW Premier Collection
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3549)
"Clean room, great A/C. Breakfast was good as well."
The price is ₹11,286
₹13,248 total
includes taxes & fees
24 Sept - 25 Sept
The Whitehall Hotel, BW Premier Collection
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2528)
"Had a wonderful stay here and staff was super friendly!"
The price is ₹16,581
₹21,017 total
includes taxes & fees
14 Sept - 15 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2101)
"Property was great, very clean and friendly staff. The location is wonderful. Will definitely stay here again. "
The price is ₹18,950
₹22,244 total
includes taxes & fees
12 Sept - 13 Sept
Hyatt Centric The Loop 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.

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile - River North

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop - Downtown featuring a river or creek

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Chicago featuring a city and modern architecture

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Sleepy Hollow Hotel Reviews

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"The staff from the start were very nice and helpful. The hotel was clean loved the location of the hotel. Will definitely try booking ag this hotel next year "
Alexander 4-night trip
Posted 3 days ago
Hotel Felix River North/Magnificent Mile
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"The staff were so welcoming! They knew it was our anniversary and we got showered with little nice surprises. Thank you so much for making our stay so memorable and meaningful. Our room was perfect, the lobby and the bar/lounge were beautiful and again the staff were great. Location is within 15 minute walk to every thing. We will definitely be back! "
Janean 4-night trip
Posted 4 days ago
The Allegro Royal Sonesta Hotel Chicago Loop

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Sleepy Hollow?

Sleepy Hollow is a neighbourhood that travellers like for its restaurants.

If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?

Yes! The majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then filter by "fully refundable" to view the top deals on offer in Sleepy Hollow.

What can I see and do in this Chicago neighbourhood?

Places you might want to visit in the area around Sleepy Hollow include Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.