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4 Stars Hotels in Sleepy Hollow, Chicago from CA $249

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Check availability on Sleepy Hollow 4 Star Hotels

This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Sleepy Hollow 4-star hotels

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

1. River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,464 reviews)
"Great place to travel!"
United States
Jared
The price is CA $264
CA $313 total
includes taxes & fees
Oct 25 - Oct 26
River Hotel
A spacious lobby with a central coffee table, sofas, and a large mirror.

2. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,382 reviews)
"Loved my stay the staff was nice and the location was great."
United States
Marta
The price is CA $253
CA $301 total
includes taxes & fees
Oct 25 - Oct 26
The Chicago Hotel Collection Ambassador Gold Coast
A grand lobby with a central bar, high ceilings, and classical architecture.

3. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,017 reviews)
"The hotel was absolutely stunning! Loved the convenience of it being right down town!"
United States
Amanda
The price is CA $282
CA $335 total
includes taxes & fees
Oct 1 - Oct 2
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
A large, historic building with a central courtyard surrounded by trees.

4. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,310 reviews)
"Great stay!"
United States
Alan
The price is CA $235
CA $321 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Chicago
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.

5. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (2,263 reviews)
"Would recommend stay here very nice hotel"
United States
carla
The price is CA $228
CA $271 total
includes taxes & fees
Oct 25 - Oct 26
The Chicago Hotel Collection - Magnificent Mile
The Intercontinental hotel facade with a large American flag and a floral display.

6. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,349 reviews)
"Great stay, perfect location would stay again"
United States
Kenan
The price is CA $373
CA $493 total
includes taxes & fees
Oct 25 - Oct 26
InterContinental Chicago Magnificent Mile by IHG
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

7. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,910 reviews)
"Lovely hotel in a great location with a great staff"
United States
Emily
The price is CA $344
CA $409 total
includes taxes & fees
Oct 30 - Oct 31
L7 Chicago by LOTTE
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

8. The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,115 reviews)
"Had a wonderful stay here"
United States
Erin
The price is CA $211
CA $251 total
includes taxes & fees
Oct 25 - Oct 26
The Wade
A modern building with a glass facade and a curved structure.

9. Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
4.0 star property
Rosemont
9.0 out of 10, Wonderful, (3,217 reviews)
"Great hotel and comfortable stay."
United States
Alison
The price is CA $250
CA $285 total
includes taxes & fees
Oct 18 - Oct 19
Hyatt Regency O'Hare Chicago
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

10. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,507 reviews)
"Great property, great staff and great locations!"
United States
Mark
The price is CA $388
CA $512 total
includes taxes & fees
Oct 30 - Oct 31
Hyatt Regency Chicago
A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

11. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,269 reviews)
"Great location close to shops and restaurants"
United Kingdom
Peter
The price is CA $211
CA $255 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Saint Clair- Magnificent Mile
A modern kitchen with a marble island, fruit bowls, and a city view.

12. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,309 reviews)
"Beautiful hotel and great location."
United States
Ruby
The price is CA $275
CA $378 total
includes taxes & fees
Oct 30 - Oct 31
Fairmont Chicago at Millennium Park
A long, narrow hallway with a patterned carpet, recessed lighting, and doors on one side.

13. Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel
4.5 star property
Rosemont
9.4 out of 10, Exceptional, (2,255 reviews)
"We always stay here when flying back to Chicago, very nice hotel"
United States
MARY
The price is CA $310
CA $353 total
includes taxes & fees
Oct 2 - Oct 3
Loews Chicago O'Hare Hotel
A dining area with a table set for four, large windows offering a cityscape view at dusk.

14. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,646 reviews)
"Great place to stay!"
United States
ShaRona
The price is CA $346
CA $457 total
includes taxes & fees
Oct 29 - Oct 30
The Royal Sonesta Chicago Downtown
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

15. Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,308 reviews)
"Great stay overall"
United States
Nathan
The price is CA $210
CA $249 total
includes taxes & fees
Oct 25 - Oct 26
Central Loop Hotel
A historic building with a prominent casino sign, surrounded by modern skyscrapers.

16. Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (3,099 reviews)
"Great hotel, very clean and amazing location"
Netherlands
Shyreen
The price is CA $220
CA $308 total
includes taxes & fees
Oct 25 - Oct 26
Hotel Felix River North/Magnificent Mile
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

17. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5,997 reviews)
"I’d stay here again."
United States
Eliana
The price is CA $264
CA $359 total
includes taxes & fees
Oct 26 - Oct 27
Embassy Suites by Hilton Chicago Downtown River North
A hotel room with a sofa, armchairs, a dining table, and a view of the city at night.

18. Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport
4.0 star property
O'Hare
8.6 out of 10, Excellent, (2,530 reviews)
"Excellent location and friendly staff."
United States
Samuel
The price is CA $289
CA $339 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Chicago O'Hare Airport
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

19. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,877 reviews)
"Great location! Would stay again!"
United States
Sharee
The price is CA $359
CA $469 total
includes taxes & fees
Oct 25 - Oct 26
LondonHouse Chicago, Curio Collection by Hilton
A cityscape with high-rise buildings, a marina, and a waterfront.

20. Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago
4.0 star property
Near South Side
9.2 out of 10, Wonderful, (1,469 reviews)
"Great hotel!!"
United States
Martin Peter
The price is CA $396
CA $512 total
includes taxes & fees
Oct 23 - Oct 24
Hyatt Regency McCormick Place Chicago
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Sleepy Hollow.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL
The price is CA $841 per night from Oct 30 to Oct 31
CA $841
CA $1,000 total
Oct 30 - Oct 31
includes taxes & fees
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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 Sleepy Hollow Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"."
Charles 3-night trip
Posted 2 hours ago
Hilton Chicago

Frequently asked questions

What are the best 4-star hotels in Sleepy Hollow?
DoubleTree by Hilton Chicago Midway Airport is highly praised by Expedia travellers. This 4-star hotel located around Sleepy Hollow guarantees an inviting guest experience and plenty of handy amenities.
How much does it cost to stay in a 4-star hotel in Sleepy Hollow?
We can help you easily locate the perfect 4-star hotel for your stay in Sleepy Hollow. Use our filter tool to fine-tune your search by things like price, amenities and hotel star rating and get access to fantastic deals in a few clicks.

  • Search for the lowest price from CA $879

What's the difference between 5-star and 4-star hotels in Sleepy Hollow?
If you choose to vacation at a 4-star hotel in Sleepy Hollow, you'll usually find loads of amenities to ensure you're relaxed, such as a pool, gym and restaurant. You can look forward to high-quality service and upscale accommodations. Go for a 5-star hotel and you'll get a few extra bells and whistles — think around-the-clock concierge, on-site spas and indulgent turndown services. You're likely to get extra amenities and exclusive services at a 5-star getaway, but both are great options for luxury guests.

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