Highland Hills Holidays from £956

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Your Highland Hills Holiday

Get ready to experience Highland Hills in your own style with a custom Highland Hills holiday package! Uncovering the best parts of this fascinating city is made easier with a base in a neighbourhood such as Clarendon Hills, which is good for golfing, among plenty of other things. Yorktown Shopping Centre and Lilacia Park 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 holiday to Highland Hills to suit your travel style, whatever that may be.

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

Hilton Chicago

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 13 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.4/10 Very Good! (1,938 reviews)
We were pushed to 'upgrade' to a lake view room, which we did for an additional $40. The room did have a wonderful view of the lake which was entirely blocked by the TV (had to unplug and move it) and the room was TINY. I wonder if all rooms are that small? We felt a bit scammed. There were stains right on top of the comforter. Only two tissues in the tissue box with plastic bubble wrap stuff underneath to make it seem like it was full. Water flooded the vanity every time we used the sink. The coffee maker had old dirty water in it. Overall, we were kind of disappointed for how expensive the hotel was. The hotel itself was beautiful but the room and amenities were underwhelming.

Reviewed on 30 Jun 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 13 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on 29 Jun 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
13 Sept - 20 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
I enjoyed every aspect of my stay here. I liked it so much the first time that I just had to stay here the second time around. The only critique that I have is that the internet is really wonky and janky to connect to. My partner and I encountered a constant connection issue whereby it would take us a longer than 5 minutes to connect to the Wi-Fi/internet for the hotel. Only after multiple retrys would the internet connection become stable.

Reviewed on 30 Jun 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 13 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
I had such a lovely staycation, and I recommend a stay here to everyone I know.

Reviewed on 26 Jun 2025

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 13 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,715 reviews)
The exceptional staff went above and beyond to ensure a fantastic stay. The breakfast buffet was outstanding, and the complimentary wine and beer in the evening was a wonderful touch, providing a well-deserved respite after a day of exploring the city.

Reviewed on 30 Jun 2025

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

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 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 £62 per night from 2 Jul to 3 Jul
£62
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (2,106 reviews)
"Breakfast was good, but the eggs had strange texture, almost like they were powdered. Nice they featured a different meat for breakfast each day. Staff was very helpful. They had some renovation going on but they were quiet. The only disappointment was our window in our room was filthy,hard ..."

Reviewed on 30 Jun 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is £140 per night from 2 Jul to 3 Jul
£140
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (1,196 reviews)
"Everything was great besides the extra fee I had to pay when I got there"

Reviewed on 30 Jun 2025

Crowne Plaza Chicago West Loop by IHG
Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is £140 per night from 2 Jul to 3 Jul
£140
2 Jul - 3 Jul
includes taxes & fees
8.6/10 Excellent! (1,692 reviews)
"Super helpful staff and very accommodating!"

Reviewed on 30 Jun 2025

Hyatt Regency O'Hare Chicago
See all 3,017 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 £956. 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

Wrigley Field featuring a city, a sporting event and city views

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
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
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

Things to do

River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago

* 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.