Title: Sleepy Hollow Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,038 Expedia.ca

[Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Chicago-Hotels.0-n6132427-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d6132427.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Sleepy Hollow Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in Sleepy Hollow

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

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $1,038

per person

May 14 - May 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (858 reviews)

Clean, friendly staff

Reviewed on Mar 10, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,253

per person

May 14 - May 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (3,438 reviews)

Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on Mar 10, 2026

![Hyatt Place Chicago/Downtown - The Loop](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

CA $1,461

per person

May 29 - Jun 1

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (1,197 reviews)

We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.

Reviewed on Mar 9, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $1,410

per person

May 15 - May 18

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (436 reviews)

Great value, friendly staff

Reviewed on Mar 8, 2026

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,633

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (1,839 reviews)

One of the best hotels I've ever stayed at

Reviewed on Mar 10, 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](https://expedia.ca/Chicago-Sleepy-Hollow.dx6132427)

![Downtown Chicago showing a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Magnificent Mile - River North](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(725 area reviews)

 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. 

[Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Chicago which includes modern architecture and a city](https://images.trvl-media.com/place/6059328/2fb61786-4c0f-40e8-ae4e-a0fad3f9539a.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Lincoln Park

5/5(20 area reviews)

 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. 

[Find hotel + flight trips in Lincoln Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Sleepy Hollow Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $131

CA $154 total

Apr 1 - Apr 2

includes taxes & fees

8/10 Very Good! (9,939 reviews)

Clean and well kept. Great Southloop location.

Reviewed on Mar 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=6132427)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $187

CA $258 total

Mar 18 - Mar 19

includes taxes & fees

9.4/10 Exceptional! (3,503 reviews)

Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on Mar 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F03%2F2026&endDate=19%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true&regionId=6132427)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

CA $166

CA $195 total

Mar 19 - Mar 20

includes taxes & fees

8.6/10 Excellent! (5,721 reviews)

Love the complimentary drinks !

Reviewed on Mar 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F03%2F2026&endDate=20%2F03%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=6132427)

[See all 4,959 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&regionId=6132427)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Sleepy Hollow vacation package cost?

### How do I get a cheap travel package to Sleepy Hollow?

### Where should I stay in Sleepy Hollow?

### How far in advance should I book my Sleepy Hollow vacation?

### What does an Expedia Sleepy Hollow travel package include?

### What should I know before booking a Sleepy Hollow travel package?

### Can I choose my airline with a Sleepy Hollow Expedia vacation package?

### If I'm not able to travel, can I cancel my Sleepy Hollow vacation package?

### Discover the most popular places to visit in Sleepy Hollow

![Wrigley Field featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. 

[](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)

### Things to do

![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 360 CHICAGO Observation Deck

CA $36

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details)

![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Flyover in Chicago

CA $52

per adult

**98%** of travellers recommend

[](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details)

![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wendella's 90-min Chicago River Architecture Tour

CA $55

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details)

[See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6132427)

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- [Flights from North Bay (YYB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyb/mdw/north-bay-to-chicago)
- [Flights from Calgary (YYC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago)
- [Flights from Toronto (YYZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago)
- [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

- [Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction)
- [Broadview Vacations ](https://www.expedia.ca/Broadview.d7064.Destination-Travel-Guides)
- [Buckingham Fountain ](https://www.expedia.ca/Buckingham-Fountain-Downtown-Chicago.d6064027.Vacation-Attraction)
- [Burbank Vacations ](https://www.expedia.ca/Burbank.d183178.Destination-Travel-Guides)
- [Cibc Theatre ](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction)
- [Carbide and Carbon Building ](https://www.expedia.ca/Carbide-And-Carbon-Building-Downtown-Chicago.d553248621555594910.Vacation-Attraction)
- [Chicago Riverwalk ](https://www.expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction)
- [Chicago Theatre ](https://www.expedia.ca/Chicago-Theatre-Downtown-Chicago.d6064049.Vacation-Attraction)
- [Chicago Vacations ](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides)
- [Clearing Vacations ](https://www.expedia.ca/Clearing.d6132083.Destination-Travel-Guides)
- [Cloud Gate ](https://www.expedia.ca/Cloud-Gate-Downtown-Chicago.d6182888.Vacation-Attraction)
- [Ernest Hemingway Museum and House ](https://www.expedia.ca/Ernest-Hemingway-Museum-And-House-Chicago.d6241604.Vacation-Attraction)
- [Frank Lloyd Wright Historic District ](https://www.expedia.ca/Frank-Lloyd-Wright-Historic-District-Chicago.d553248634340947645.Vacation-Attraction)
- [Garfield Park Conservatory ](https://www.expedia.ca/Garfield-Park-Conservatory-East-Garfield-Park.d6182807.Vacation-Attraction)
- [Grant Park ](https://www.expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)
- [Hometown Vacations ](https://www.expedia.ca/Hometown.d6132133.Destination-Travel-Guides)
- [House of Blues Chicago ](https://www.expedia.ca/House-Of-Blues-Chicago-Downtown-Chicago.d6227753.Vacation-Attraction)
- [Loretto Hospital ](https://www.expedia.ca/Loretto-Hospital-Austin.d553248635997986962.Vacation-Attraction)
- [Marina City ](https://www.expedia.ca/Marina-City-Downtown-Chicago.d553248621533116577.Vacation-Attraction)
- [Millennium Park ](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
- [Obama's House ](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction)
- [Richard J. Daley Center ](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction)
- [River Forest Vacations ](https://www.expedia.ca/River-Forest.d5986.Destination-Travel-Guides)
- [Robie House ](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)
- [South Loop Vacations ](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides)
- [The East Bank Club ](https://www.expedia.ca/The-East-Bank-Club-Downtown-Chicago.d553248621555594881.Vacation-Attraction)
- [The Loop Vacations ](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides)
- [United Center ](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)
- [Unity Temple ](https://www.expedia.ca/Unity-Temple-Chicago.d6064079.Vacation-Attraction)
- [Willis Tower ](https://www.expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)

- [Ace Rental Cars in Midway Intl. ](https://www.expedia.ca/Ace-Car-Rentals-In-Midway-Intl.d5719117-c2.Car-Rental-Guide-Suppliers)
- [Budget Rental Cars in Midway Intl. ](https://www.expedia.ca/Budget-Car-Rentals-In-Midway-Intl.d5719117-c39.Car-Rental-Guide-Suppliers)
- [Rental cars Midway Intl. airport ](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide)
- [Dollar Rent A Car Rental Cars in Midway Intl. ](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Midway-Intl.d5719117-c43.Car-Rental-Guide-Suppliers)
- [Enterprise Rental Cars in Midway Intl. ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Midway-Intl.d5719117-c15.Car-Rental-Guide-Suppliers)
- [Express Travel Group Rental Cars in Midway Intl. ](https://www.expedia.ca/Express-Travel-Group-Car-Rentals-In-Midway-Intl.d5719117-c1124.Car-Rental-Guide-Suppliers)
- [Hertz Rental Cars in Midway Intl. ](https://www.expedia.ca/Hertz-Car-Rentals-In-Midway-Intl.d5719117-c40.Car-Rental-Guide-Suppliers)
- [Van Car Rentals near Midway Intl. ](https://www.expedia.ca/Van-Car-Rentals-In-Midway-Intl.d5719117-tVan.Car-Rental-Guide-Class)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.