Sleepy Hollow Vacations from $389

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Your Sleepy Hollow Vacation

Experience everything this neighborhood has to offer with a tailor-made Sleepy Hollow vacation package. However you picture yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. What to cross off your itinerary first? Nearby Balzekas Museum of Lithuanian Culture is one thing you can't miss during your trip to Sleepy Hollow. Expedia will help turn your dream Sleepy Hollow vacation into reality, whatever your travel plans or budget.

The Latest Sleepy Hollow Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Chicago Lake Shore Hotel

Kenwood

Save 100% on your flight

$389

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7/10 Good! (1,004 reviews)

My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!

Reviewed on Sep 22, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$613

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (561 reviews)

I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!

Reviewed on Sep 21, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$732

per person

Nov 24 - Nov 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious

Reviewed on Sep 23, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$656

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!

Reviewed on Sep 19, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$589

per person

Dec 8 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,512 reviews)

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Sleepy Hollow Hotel Deals

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$179 nightly

$213 total

Sep 27 - Sep 28

Total with taxes and fees

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$188 nightly

$223 total

Sep 27 - Sep 28

Total with taxes and fees

8/10 Very Good! (10,192 reviews)

"I’ve stayed here for years. Every riot"

Reviewed on Sep 22, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$206 nightly

$245 total

Sep 27 - Sep 28

Total with taxes and fees

8/10 Very Good! (2,305 reviews)

"It started out with someone from the desk, being kind enough to get a luggage cart, for us to load and take things to the room. We were not given information regarding breakfast or the rest of the hotel, nor was there anything in the room. The sink in the bathroom was cracked and leaked on the floor ..."

Reviewed on Sep 23, 2026

See all 4,719 properties in Sleepy Hollow

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.