Highland Hills Holidays from £1,319

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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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,748, price is now £1,319 per person
£1,319
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (2,267 reviews)
Loved it

Reviewed on 1 Aug 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,167, price is now £1,333 per person
£1,333
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Comes with all the comforts of Home.

Reviewed on 29 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,354, price is now £1,655 per person
£1,655
per person
11 Sept - 17 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £2,255, price is now £1,663 per person
£1,663
per person
16 Sept - 23 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on 30 Jul 2026

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Downtown Chicago
Price was £2,339, price is now £1,794 per person
£1,794
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,009 reviews)
This hotel was absolutely beautiful! The perfect location, and I mean THE PERFECT LOCATION! The staff and bartenders were amazing! Definitely recommend staying here!

Reviewed on 29 Jul 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
A busy city street with tall buildings, a bus, and cars.

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 £80 per night from 16 Aug to 17 Aug
£80
16 Aug - 17 Aug
includes taxes & fees
SureStay Plus Hotel by Best Western Chicago Lombard
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £143 per night from 30 Aug to 31 Aug
£143
30 Aug - 31 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
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 £213 per night from 20 Aug to 21 Aug
£213
20 Aug - 21 Aug
includes taxes & fees
Crowne Plaza Chicago West Loop by IHG
See all 3,172 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 £1,319. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£32
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.