Highland Hills Holidays

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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.
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 30 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,730 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,713
    £1,296
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 30 - Aug 3

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,534 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,877
    £1,398
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-sized fridge, microwave, oven, stovetop
    Aug 20 - Aug 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (489 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,964
    £1,495
    per traveller
    found 7 hours ago
    Level Chicago – Old Town
  • Dinner served
    Jul 30 - Aug 4

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,005 reviews)
    "Nice staff clean room would stay again."
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £2,062
    £1,606
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Breakfast and dinner served
    Jul 30 - Aug 3

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,797 reviews)
    "beautiful room city view excellent location quiet and comfortable"
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,701
    £1,330
    per traveller
    found 1 day ago
    Omni Chicago Hotel

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

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 £77 per night from 21 Jun to 22 Jun
£77
21 Jun - 22 Jun
includes taxes & fees
9/10 Wonderful! (2,786 reviews)
"Clean, affordable, and safe location. Would recommend."

Reviewed on 9 Jun 2026

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 £136 per night from 28 Jun to 29 Jun
£136
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,638 reviews)
"Upsetting that I was given a room that I had to haul all of my luggage up 16 steep stairs. No other room options. I had reserved a room months in advance. The front desk lady said a few stairs, which I found odd being that there is an elevator. Beware…the top floor is by stairs only! Front desk lady ..."

Reviewed on 9 Jun 2026

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 £140 per night from 1 Jul to 2 Jul
£140
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (2,240 reviews)
"It was a great choice if you want to be in the west loop area. Easy to walk to places. Clean and great staff!"

Reviewed on 8 Jun 2026

Crowne Plaza Chicago West Loop by IHG
See all 3,222 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 . 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

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Millennium Park

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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.