Title: Highland Hills Vacation Packages 2026 from $264 | Expedia.com

[Highland Hills Travel Guide](https://expedia.com/Chicago-Highland-Hills.dx6132236)[Hotels in Highland Hills](https://expedia.com/Highland-Hills-Chicago-Hotels.0-n6132236-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.com/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.com/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Car Rentals in Highland Hills](https://expedia.com/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 Vacations from $264

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 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.com/Yorktown-Shopping-Center-Chicago.d6227539.Vacation-Attraction) and [Lilacia Park](https://www.expedia.com/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.

## The Latest Highland Hills Vacation Packages

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

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$264

per person

Apr 24 - Apr 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,365 reviews)

Room neat, clean and cozy. Check in was easy. Small and intimate for quick weekend getaway.

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

Save 100% on your flight

$390

per person

Apr 24 - Apr 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

The room was excellent

Reviewed on Feb 16, 2026

![Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/2123ebc4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

$415

per person

Apr 30 - May 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (999 reviews)

Enjoyed the room. The staff could use a hug not the friendliest. The games our outdated. Seen many guest besides me decide to go play at the other area casino

Reviewed on Jan 1, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$388

per person

Apr 24 - Apr 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$365

per person

Apr 24 - Apr 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,008 reviews)

Clean n great view. 7.5/10\. Make sure to ask for microwave nd mini fridge might not have one in the room but they have some available to bring up.

Reviewed on Feb 16, 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.com/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.com/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 illuminated at night showcasing vibrant lights and cultural attractions in Chicago, Illinois](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.com/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 which includes 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(9,481 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.com/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.com/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

4/5(776 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.com/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/w3838h2556x2y3-00664b38_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

$72 nightly

$80 total

Feb 17 - Feb 18

Total with taxes and fees

9/10 Wonderful! (2,559 reviews)

The entire staff was very accommodating and friendly. The rooms were very well stocked and clean. Less than 5 minutes(or less) away from dozens of restaurants and stores too.

Reviewed on Feb 12, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F17%2F2026&endDate=2%2F18%2F2026&selected=10641&PinnedHotelID=10641&HadPinnedHotel=true&regionId=6132236)

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_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

$196 nightly

$230 total

Mar 14 - Mar 15

Total with taxes and fees

8.2/10 Very Good! (2,202 reviews)

Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on Feb 9, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F14%2F2026&endDate=3%2F15%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true&regionId=6132236)

![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Chicago Dwtn - The Mart by IHG

350 West Wolf Point Plaza, Building 2 Chicago IL

Fully refundable

$123 nightly

$144 total

Feb 27 - Feb 28

Total with taxes and fees

8.8/10 Excellent! (2,166 reviews)

I would definitely stay here again. All of the staff were friendly and helpful. The hotel's view of the city is

Reviewed on Feb 11, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&selected=5467&PinnedHotelID=5467&HadPinnedHotel=true&regionId=6132236)

[See all 3,280 properties in Highland Hills](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F17%2F2026&endDate=2%2F18%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.com/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.com/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)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

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

![Wrigley Field featuring cbd, a sporting event and a city](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.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.com/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

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.com/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

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

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

### Things to do

![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Bulls Basketball Game at United Center

$166

per adult

**80%** of travellers recommend

[](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.activity-details)

![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago: Navy Pier Centennial Wheel Ticket

$25

per adult

**88%** of travellers recommend

[](https://expedia.com/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details)

![Picture 7 for Activity Chicago River: 1.5-Hour Guided Architecture Cruise](https://mediaim.expedia.com/localexpert/4575180/37c87b99-f11d-4fe0-8f87-3e8f807e4c0c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago River: 1.5-Hour Guided Architecture Cruise

$44

per adult

**98%** of travellers recommend

[](https://expedia.com/things-to-do/chicago-river-15-hour-guided-architecture-cruise.a4575180.activity-details)

[See all activities in Chicago](https://expedia.com/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.