Highland Hills Holidays from £929

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Your Highland Hills Holiday

Take the hard work out of travel planning with a Highland Hills holiday package. One of the best neighbourhoods to stay in this exciting city is Clarendon Hills, which is good for golfing and a lot more. Eager to do some sightseeing? A trip to Highland Hills wouldn't be complete without visiting Yorktown Shopping Centre, Lilacia Park and other top attractions. A couple of quick clicks is all it takes to put together the ultimate Highland Hills holiday on Expedia.

Prices and availability subject to change. Additional terms may apply.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on 10 Jan 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The staff are thoughtful and provide the best service. While I was there, I was already planning to come back and stay there again!

Reviewed on 24 Apr 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
22 Jul - 25 Jul
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on 15 Apr 2024

Hotel Arista

Hotel Arista

4.5 out of 5
per person
1 Jun - 5 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
It was a really nice stay. we had the king size bed room. It’s a really nice hotel. The only reason I took one star off was because the bed was very firm and about knee-high and the pillows were also very hard. I don’t know if they have rooms that have softer beds, but for that reason, I would never stay there again.

Reviewed on 26 Apr 2024

Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
Bedford Park
per person
1 Jun - 5 Jun
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
One of the things I didn't like was I asked for a room with a pull-out couch and a queen bed. I got a queen bed with no pull-out couch and I was told that the rooms were not clean and this was at 5:00 p.m..

Reviewed on 23 Apr 2024

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
Downtown Chicago featuring a city

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 hotels in Downtown Chicago

Top hotels in Highland Hills

SureStay Plus Hotel by Best Western Chicago Lombard
SureStay Plus Hotel by Best Western Chicago Lombard
2.5 out of 5
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is £68 per night from 29 Apr to 30 Apr
£68
per night
29 Apr - 30 Apr
8.6/10 Excellent! (1,485 reviews)
"good"

Reviewed on 23 Apr 2024

SureStay Plus Hotel by Best Western Chicago Lombard
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3.5 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is £150 per night from 28 Apr to 29 Apr
£150
per night
28 Apr - 29 Apr
8.6/10 Excellent! (1,003 reviews)
Perfect location in downtown!
"The view was amazing. Room was clean and the front desk employees were the best."

Reviewed on 23 Apr 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
3 out of 5
1 S Franklin Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £124 per night from 12 May to 13 May
£124
per night
12 May - 13 May
8.6/10 Excellent! (2,334 reviews)
"The bath linen had hair on it. Otherwise, everything was fine."

Reviewed on 23 Apr 2024

La Quinta Inn & Suites by Wyndham Chicago Downtown
See all 2,786 properties in Highland Hills
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Highland Hills travel package cost?
Live it up in Highland Hills from as low as £929. Choose from a great selection of rental cars, hotels and flights to suit your budget. You can pick up even better deals when you add a few tours or activities to your travel package.
If I'm not able to travel, can I cancel my Highland Hills travel package?
Yes, you can cancel your Highland Hills booking if your travel plans have changed. Whether you’ll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Highland Hills?
Combine your bookings with Expedia to save on your next trip. With over 550 airlines and 1,000,000 hotel options globally, your Highland Hills travel package can be tailored exactly to suit your budget. With all that extra cash, why not add some awesome tours and activities? It’s an easy way to unlock even more savings. That dream holiday to Highland Hills is closer than you thought!
Does Expedia offer Book Now, Pay Later Highland Hills holidays?
Expedia has partnered with online lender Klarna to make your next getaway a little easier on the wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to splash while you’re away. Klarna has several payment plans to pick from, so you’re sure to find one that fits into your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday over multiple transactions.
  • Low deposit holidays: Clicking on the “book now” button is easier with this payment option. Simply put down a small deposit on your booking and then start working on your travel plans.

Where should I stay in Highland Hills?
A holiday in Highland Hills wouldn’t be complete without visiting Yorktown Shopping Centre. Why not book a hotel within walking distance of this popular tourist attraction?
What are the top hotels in Highland Hills?
SureStay Plus Hotel by Best Western Chicago Lombard and Hyatt Place Chicago/Lombard/Oak Brook are a couple of the most sought-after properties in Highland Hills. Why not look up the amenities and rates at each and then make a decision?
How far in advance should I book my Highland Hills holiday?
Reserving your seat early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months prior to departure dates. This is often the cheapest time to book. If circumstances have left you booking late, discount tickets to Highland Hills are still known to appear just a few weeks before departure.
What does an Expedia Highland Hills travel package include?
It all boils down to what kind of trip you’re contemplating. Highland Hills holiday deals can include car rentals, flights and hotels. You can mix and match to create the bundle that suits your needs. You can also add on experiences and activities after you’ve booked to land even bigger discounts.
What should I know before booking a Highland Hills travel package?
Design deals that suit your budget with an Expedia package. Hotels, airfares, rental cars — we’ve got them all. You’ll save a tidy sum just by combining your bookings. Whether you’re embarking on a ski adventure or relaxing on a sunny beach, your perfect getaway is just clicks away.
Can I choose my airline with a Highland Hills Expedia travel package?
Yes, definitely. Expedia has more than 550 partner airlines to pick from across the world. With all that choice, finding the perfect carrier to whisk you off to Highland Hills will be a snap.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4/5(125 reviews)

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

Navy Pier

Things to do

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

£43
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

£59
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.