Highland Hills Holidays

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  • Better together

    Save up to €900 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Bar (on property)
    Jul 16 - Jul 20

    The Whitehall Hotel, BW Premier Collection + Flight

    Downtown Chicago
    4 nights
    3.5 star property
    8.4/10 - Very good (3,935 reviews)
    "All good no issues"
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,289
    €1,009
    per traveller
    found 1 day ago
    The Whitehall Hotel, BW Premier Collection
  • Lobby sitting area
    Jul 16 - Jul 20

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.4/10 - Very good (1,967 reviews)
    "The staff was able to help us get a room earlier than the check-in time."
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,427
    €1,050
    per traveller
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Smart TV
    Jul 16 - Jul 20

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,600
    €1,196
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Breakfast and dinner served
    Jul 16 - Jul 20

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,799 reviews)
    "Best hotel in Chicago for the price. Perfect location. The staff was very friendly. The rooms are stylish and spacious. One minor inconvenience is that they do not offer room service but I was able to put an order in at the restaurant and pick up was fast and easy."
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,437
    €1,108
    per traveller
    found 1 day ago
    Omni Chicago Hotel
  • Terrace/patio
    Jul 16 - Jul 20

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

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,535 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 • Direct ORD - DUB • Direct
    €1,564
    €1,224
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

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 €88 per night from 23 Jun to 24 Jun
€88
23 Jun - 24 Jun
includes taxes & fees
9/10 Wonderful! (2,788 reviews)
"Great stay"

Reviewed on 10 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 €157 per night from 28 Jun to 29 Jun
€157
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,640 reviews)
"Hotel was clean, very friendly staff and conveniently located from the airport"

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 €161 per night from 1 Jul to 2 Jul
€161
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 3,166 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.

Frequently asked questions

How much does a Highland Hills holiday package cost?
We make it easy to travel somewhere new, with Highland Hills holiday packages starting from as low as . You'll have the flexibility to combine your favourite airlines, hotels and car rental. For the ultimate escape, why not add a couple of tours and experiences to your travel itinerary?
How do I get a cheap travel package to Highland Hills?
If you love landing a bargain, bundle your bookings into a Highland Hills holiday package. Whether you're chasing hotels, flights, rental cars or day tours, you can book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 hotel options worldwide to choose from. Fly with who you prefer, stay wherever you like and save a pretty penny — now that's the perfect holiday!
Where should I stay in Highland Hills?
There's so much to see in Highland Hills, so spend your nights close to its top attractions and treat yourself to more time sightseeing. Yorktown Shopping Centre is one spot to put on your must-see list.
What are the top hotels in Highland Hills?
Sonesta ES Suites Chicago - Lombard and SureStay Plus Hotel by Best Western Chicago Lombard are a couple of the most sought-after properties in Highland Hills. Why not have a look at the facilities and rates at each and then decide?
How far in advance should I book my Highland Hills holiday?
While not all air carriers release ticket prices early, you can usually look up international fares on Expedia up to 12 months in advance. This is when you'll score some incredible bargains. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the cheapest prices emerge only weeks before departure.
What does an Expedia Highland Hills travel package include?
Expedia has all you need to arrange your Highland Hills trip, but what your package looks like is your choice. Select from any combination of flights, hotels and rental cars. In search of some experiences or tours to keep you busy? Once you've made your booking, you can add them on too. No matter your style or budget, there's a deal to suit your needs.
What should I know before booking a Highland Hills travel package?
Bundling your bookings into a Highland Hills holiday package is the most convenient way to organise your trip. Not only that, you'll save just for combining your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Highland Hills Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our holiday packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Highland Hills holiday package?
Don't worry if you're rethinking your Highland Hills holiday package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realise life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.

Popular places to visit

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
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

5/5(1 review)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
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.