Title: Highland Hills Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $801 Expedia.ca

[Hotels in Highland Hills](https://expedia.ca/Highland-Hills-Chicago-Hotels.0-n6132236-0.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)[Highland Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Hills.d6132236.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)

# Highland Hills 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

#### Your Highland Hills Vacation

Get ready to experience Highland Hills in your own style with a custom Highland Hills vacation package! Uncovering the best parts of this fascinating city is made easier with a base in a neighborhood such as Clarendon Hills, which is good for golfing, among plenty of other things. [Yorktown Shopping Center](https://www.expedia.ca/Yorktown-Shopping-Center-Chicago.d6227539.Vacation-Attraction) and [Lilacia Park](https://www.expedia.ca/Lilacia-Park-Chicago.d6247243.Vacation-Attraction) are some of the major attractions to tour during a trip to Highland Hills. Expedia is here to help you escape your routine. Tailor your vacation to Highland Hills to suit your travel style, whatever that may be.

## Top Holiday Package Deals in Highland Hills

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

![Wind Creek Southland Casino and Hotel](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/1fba48a9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Wind Creek Southland Casino and Hotel

East Hazel Crest

CA $801

per person

Apr 23 - Apr 28

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (MDW)

9.4/10 Exceptional! (160 reviews)

The room was very clean but the lighting in the room is very dark.

Reviewed on Mar 2, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $920

per person

Apr 22 - Apr 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (413 reviews)

Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 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 $1,274

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Great breakfast buffet! Great location to Michigan Ave. I would stay here again.

Reviewed on Mar 3, 2026

![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/90cf0aed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Banque Hotel

CA $1,146

per person

May 3 - May 9

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (467 reviews)

Room was amazing and beautiful and comfortable Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous

Reviewed on Mar 1, 2026

![4BR Corporate Suite Central and Modern](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 4BR Corporate Suite Central and Modern

Near North Side

CA $1,586

per person

Apr 23 - Apr 28

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

10/10 Exceptional! (8 reviews)

Our stay at Envitae was amazinggg!! I’m so glad I booked with them for my Chicago trip with my family. The place was so nice and clean and decorated nicely and looks exactly like the pictures! This place literally had everything we needed and was so accommodating from having soap and shampoo to pots and pans pretty anything you could think of that you may need they had stocked. Also they were checking in with us to make sure our stay was going well they even were so kind to send us gourmet doughnuts!! The views were amazing and the location was literally near everything you could think of in walking distance. I would definitely book here again! Thank you so much for having us!

Reviewed on Jan 30, 2026

## Where to stay in Highland Hills

Find the best Highland Hills areas and neighborhoods for the activities you enjoy most. [Learn more about Highland Hills](https://expedia.ca/Chicago-Highland-Hills.dx6132236)

![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)

![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### O'Hare

3.5/5(38 area reviews)

 Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates. 

[Find hotel + flight trips in O'Hare](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=O%27Hare&DestID=553248635074842747&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Highland Hills Hotel Deals

![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/6e52464b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

Fully refundableReserve now, pay when you stay

CA $98

CA $109 total

Mar 4 - Mar 5

includes taxes & fees

9/10 Wonderful! (2,589 reviews)

Very comfortable stay

Reviewed on Mar 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=10641&PinnedHotelID=10641&HadPinnedHotel=true&regionId=6132236)

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

CA $268

CA $315 total

Mar 27 - Mar 28

includes taxes & fees

8.4/10 Very Good! (2,221 reviews)

great stay

Reviewed on Mar 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=27%2F03%2F2026&endDate=28%2F03%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true&regionId=6132236)

![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/2c5e0afa_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

CA $167

CA $190 total

Mar 4 - Mar 5

includes taxes & fees

8.8/10 Excellent! (2,383 reviews)

very clean, comfortable, and the breakfast is amazing.!

Reviewed on Mar 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=5403&PinnedHotelID=5403&HadPinnedHotel=true&regionId=6132236)

[See all 3,297 properties in Highland Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&regionId=6132236)

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 Highland Hills vacation package cost?

### How do I get a cheap travel package to Highland Hills?

### Where should I stay in Highland Hills?

### What are the top hotels in Highland Hills?

### How far in advance should I book my Highland Hills vacation?

### What does an Expedia Highland Hills travel package include?

### What should I know before booking a Highland Hills travel package?

### Can I choose my airline with a Highland Hills Expedia vacation package?

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

### Discover the most popular places to visit in Highland Hills

![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

![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)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**96%** of travellers recommend

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

![cruise ship sailing past navy pier in chicago](https://mediaim.expedia.com/localexpert/173241/21d8d1a0-e61c-4298-ab2f-118c1794b450.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### City Cruises Chicago: Lake Michigan Premier Dinner Cruise

CA $225

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.activity-details)

[See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6132236)

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