Title:  Sleepy Hollow Vacation Packages & Trips 2025 from $350 | 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

-   ## 
    
    Plan, book, travel with confidence
    

### 

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.

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $782

per person

Dec 24 - Dec 27

found 24 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.2/10 Wonderful! (291 reviews)

The lounge/restaurant had very good food at reasonable prices. Our room was very clean as were the common areas. Staff were friendly and helpful.

Reviewed on Oct 3, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-27/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=z3t8Y2T71m0S8JmZE9iPjRR7mCXzSmzhmmBjTTdjeCzE_9RoDRGTqssCV-dPTXnn)

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $1,200

per person

Nov 5 - Nov 9

found 21 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on Sep 29, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-05/2025-11-09/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=9BfpBBk4iFRtCBx0_Y_KrVGI4Pb7f82AQB-E5awbFCxLem_uDJaA2r_hpgzxc3ZH)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,445

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Clean room. Great staff

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-18/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=XBY0kV5V5XBRNPOf7I-0O74hDKTF33NJTo0vPM8GmAGGh7MJoLuCsxNLuFtMX6BY)

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $1,046

per person

Nov 22 - Nov 24

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Awesome room amazing tub even better service

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-24/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=Dl2JUO3-f40FStLPqC9CcCZ4Ndg__hBk9O9yT5xbJG9vaBLfE4jfXGjUjM99TXU4)

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago O'Hare Airport

O'Hare

CA $1,138

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

8.2/10 Very Good! (2,123 reviews)

Airport adjacent. It is terribly overpriced. The one saving grace is LOCATION.

Reviewed on Oct 3, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-18/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8058&paandie=true&dealMarker=XBY0kV5V5XBRNPOf7I-0O4etKy5rzQAO3k6uSv5iPU6b2UgZIrr6cGtspGRVG8oK)

## 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Chicago

5 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.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://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.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)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.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://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.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/a9ee91b7_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 $178

CA $209 total

Nov 2 - Nov 3

includes taxes & fees

7.8/10 Good! (9,387 reviews)

"Top Lage, sehr zentral"

Reviewed on Oct 1, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=6132427)

![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Freehand Chicago

19 East Ohio Street, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $138

CA $228 total

Oct 27 - Oct 28

includes taxes & fees

7.8/10 Good! (2,412 reviews)

Good for 3 nights

"The price was right, the location excellent for shopping, riverwalk, other attractions within walking distance. The rooms are tiny, the bar and breakfast inconsistent. The mattress was terrible and needs to be replaced. The lobby area is beautifully refurbished and a place to spend time reading, ..."

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=27%2F10%2F2025&endDate=28%2F10%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true&regionId=6132427)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $263

CA $309 total

Nov 3 - Nov 4

includes taxes & fees

8.4/10 Very Good! (5,029 reviews)

"staff friendly"

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=6132427)

[See all 4,725 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&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?

> Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting CA $782. When you bundle your flights, hotels and more into a package, you'll land the lowest prices.

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

> Book everything in the one place with our Sleepy Hollow vacation packages. We have incredible bargains on hotels, flights, tours and more that'll keep your travel budget happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match as you like.

### Where should I stay in Sleepy Hollow?

> There's plenty to do in Sleepy Hollow, so stay near its best attractions and spend more time sightseeing. Balzekas Museum of Lithuanian Culture is one spot to put on your must-see list.

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

> Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Sleepy Hollow sometimes emerge a few weeks before departure.

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

> Expedia has everything you need to lock in Sleepy Hollow trip, but what goes into your package is your call. Select from any combination of rental cars, flights and hotels. Chasing some experiences or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your style, there's a package to meet your needs.

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

> Booking all the parts of your getaway together is a great way to save. Bundle your airfares, rental cars and hotels into a neat package. But your options don't end at hotels. Expedia has all kinds of properties, including vacation rentals like beachside villas and city apartments. You've got choices galore!

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

> Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply select the carrier that suits you and craft your ideal Sleepy Hollow getaway.

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

> Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, have a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for more information.

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

![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

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)

![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

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](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

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

![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Architecture River Tour

CA $67

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details)

![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Architecture Center River Cruise aboard First Lady

CA $77

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

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

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-   [Flights from Michigan City (MGC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago)
-   [Flights from Minneapolis (MSP) to Chicago (MDW)](https://www.expedia.ca/lp/flights/msp/mdw/minneapolis-to-chicago)
-   [Flights from Ogdensburg (OGS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ogs/mdw/ogdensburg-to-chicago)
-   [Flights from Ontario (ONT) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ont/mdw/ontario-to-chicago)
-   [Flights from Plattsburgh (PBG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/pbg/mdw/plattsburgh-to-chicago)
-   [Flights from Philadelphia (PHL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago)
-   [Flights from South Bend (SBN) to Chicago (MDW)](https://www.expedia.ca/lp/flights/sbn/mdw/south-bend-to-chicago)
-   [Flights from Seattle (SEA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/sea/mdw/seattle-to-chicago)
-   [Flights from Brandon (YBR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago)
-   [Flights from Edmonton (YEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago)
-   [Flights from Hamilton (YHM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago)
-   [Flights from Halifax (YHZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhz/mdw/halifax-to-chicago)
-   [Flights from Kelowna (YLW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago)
-   [Flights from Ottawa (YOW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago)
-   [Flights from Peterborough (YPQ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago)
-   [Flights from Québec (YQB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago)
-   [Flights from Windsor (YQG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqg/mdw/windsor-to-chicago)
-   [Flights from Moncton (YQM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqm/mdw/moncton-to-chicago)
-   [Flights from Thunder Bay (YQT) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqt/mdw/thunder-bay-to-chicago)
-   [Flights from Sudbury (YSB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago)
-   [Flights from Timmins (YTS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago)
-   [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago)
-   [Flights from Montreal (YUL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago)
-   [Flights from Vancouver (YVR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yvr/mdw/vancouver-to-chicago)
-   [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago)
-   [Flights from Saskatoon (YXE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yxe/mdw/saskatoon-to-chicago)
-   [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.