Sleepy Hollow Vacations from $456

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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.

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$456

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$561

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$507

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,340 reviews)

great location, room and breakfast is very good and various

Reviewed on Oct 2, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$536

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,003 reviews)

We had such a great experience at Harrah’s Casino & Hotel! We stayed for one night to celebrate my birthday, and everything was wonderful from start to finish. Our room was nice, clean, and comfortable, and the staff was absolutely amazing—everyone we interacted with was so friendly and welcoming. The casino was a lot of fun, and we also had lunch at Cross Street Grill. The food was delicious, the prices were great, and it was such a convenient option right on site. Overall, we had an amazing birthday getaway and would definitely recommend Harrah’s to anyone looking for a fun and relaxing trip. We’re already talking about planning our next visit!

Reviewed on Sep 29, 2026

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$480

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,120 reviews)

Good location and parking, but the room has poor soundproofing, we can here the noise from outside

Reviewed on Oct 2, 2026

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

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$113 nightly

$135 total

Nov 2 - Nov 3

Total with taxes and fees

8/10 Very Good! (10,142 reviews)

"Housekeeping woke me up early in the morning by banging on the door. Otherwise okay"

Reviewed on Oct 2, 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$167 nightly

$199 total

Nov 1 - Nov 2

Total with taxes and fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Nov 1 - Nov 2

Total with taxes and fees

See all 4,764 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.