
Cheap Holidays to Sleepy Hollow
- Top deals for trips to Sleepy Hollow
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top deals for trips to Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'197, price is now CHF 806 per person
CHF 806
per person
found 1 day ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.

4.0-star property
The Emily Hotel
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'210, price is now CHF 852 per person
CHF 852
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'716, price is now CHF 1'249 per person
CHF 1'249
per person
found 1 day ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
Hilton Chicago O'Hare Airport
O'Hare
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'246, price is now CHF 912 per person
CHF 912
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Chicago O'Hare Airport. During your stay, you'll be connected to the airport and close to Allstate Arena. Free WiFi in public areas, a free round-trip airport shuttle and 2 restaurants are available.

4.5-star property
Pendry Chicago
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'214, price is now CHF 898 per person
CHF 898
per person
found 1 day ago
Our customers tell us they can't get enough of Pendry Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
Sleepy Hollow Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
3 Apr - 6 Apr
3 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 864, price is now CHF 739 per person
CHF 739
per person
found 8 hours ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
3 Apr - 6 Apr
3 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'070, price is now CHF 777 per person
CHF 777
per person
found 8 hours ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.

4.5-star property
Pendry Chicago
Downtown Chicago
3 Apr - 6 Apr
3 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'014, price is now CHF 836 per person
CHF 836
per person
found 8 hours ago
Our customers tell us they can't get enough of Pendry Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
3 Apr - 6 Apr
3 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 975, price is now CHF 804 per person
CHF 804
per person
found 8 hours ago
Level Chicago – Old Town's great location gets high marks from our customers. During your stay, you're just a quick walk from State Street. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.

4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
3 Apr - 6 Apr
3 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 950, price is now CHF 814 per person
CHF 814
per person
found 8 hours ago
Our customers tell us that they can't get enough of the helpful staff at theWit Chicago, a Hilton Hotel. During your stay, you're just a quick walk from Chicago Riverwalk. Features include 2 bars, a full-service spa and a restaurant.
Sleepy Hollow Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'197, price is now CHF 806 per person
CHF 806
per person
found 1 day ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'716, price is now CHF 1'249 per person
CHF 1'249
per person
found 1 day ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

4.5-star property
Pendry Chicago
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'214, price is now CHF 898 per person
CHF 898
per person
found 1 day ago
Our customers tell us they can't get enough of Pendry Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'190, price is now CHF 899 per person
CHF 899
per person
found 1 day ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
13 Apr - 18 Apr
5 night stay
Geneva (GVA) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'368, price is now CHF 1'038 per person
CHF 1'038
per person
found 1 day ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
Sleepy Hollow Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'156, price is now CHF 730 per person
CHF 730
per person
found 1 day ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'869, price is now CHF 1'170 per person
CHF 1'170
per person
found 1 day ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
The Emily Hotel
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'210, price is now CHF 852 per person
CHF 852
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.

4.0-star property
Hilton Chicago O'Hare Airport
O'Hare
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'246, price is now CHF 912 per person
CHF 912
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Chicago O'Hare Airport. During your stay, you'll be connected to the airport and close to Allstate Arena. Free WiFi in public areas, a free round-trip airport shuttle and 2 restaurants are available.

4.5-star property
Virgin Hotels Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'131, price is now CHF 855 per person
CHF 855
per person
found 1 day ago
Sports Illustrated Resorts Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a coffee shop/cafe.
Best Sleepy Hollow hotel deals for your holiday

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CHF 127 per night
CHF 127
14 Feb - 15 Feb
includes taxes & fees
11.9 km from Sleepy Hollow
Our customers tell us they can't get enough of Congress Plaza Hotel's great location. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Kostenloses WLAN
Restaurant

Hilton Chicago
720 S Michigan Ave Chicago IL
The price is CHF 146 per night
CHF 146
1 Feb - 2 Feb
includes taxes & fees
11.69 km from Sleepy Hollow
Our customers tell us they can't get enough of Hilton Chicago's great location. During your stay, you're just a quick walk from State Street. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.
Pool
Whirlpool

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is CHF 104 per night
CHF 104
25 Jan - 26 Jan
includes taxes & fees
12.91 km from Sleepy Hollow
The free breakfast at Embassy Suites by Hilton Chicago Downtown River North gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a free manager's reception, plus an indoor pool and a restaurant.
Pool
Frühstück inbegriffen

The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
The price is CHF 150 per night
CHF 150
25 Jan - 26 Jan
includes taxes & fees
12.66 km from Sleepy Hollow
The sightseeing around The Royal Sonesta Chicago Downtown gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as a restaurant, a 24-hour gym and a bar.
Haustierfreundlich
Kostenloses WLAN

River Hotel
75 East Wacker Drive Chicago IL
The price is CHF 78 per night
CHF 78
30 Jan - 31 Jan
includes taxes & fees
12.68 km from Sleepy Hollow
Our customers tell us that they can't get enough of the helpful staff at River Hotel. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a gym. This property offers pet-friendly amenities, such as food and water bowls.
Haustierfreundlich
Kostenloses WLAN

DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
The price is CHF 80 per night
CHF 80
1 Feb - 2 Feb
includes taxes & fees
13.42 km from Sleepy Hollow
Our customers tell us that they can't get enough of the sightseeing around DoubleTree by Hilton Chicago - Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus an outdoor pool and a restaurant.
Pool
Haustierfreundlich
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.
Cheap flights to Sleepy Hollow
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
ORD
Chicago
CHF 336 Return, found 12 hours ago
CHF 336
Return
found 12 hours ago
LAX
Los Angeles
ORD
Chicago
CHF 344 Return, found 12 hours ago
CHF 344
Return
found 12 hours ago
LAX
Los Angeles
ORD
Chicago
CHF 363 Return, found 12 hours ago
CHF 363
Return
found 12 hours ago
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^Savings based on all package bookings with Flight + Hotel made on ebookers.ch from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
