Highland Hills Holidays

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    Save up to NZ$2,400 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Rooftop bar, al fresco dining, open daily
    Jul 17 - Jul 18

    The Godfrey Hotel Chicago + Flight

    Downtown Chicago
    1 night
    4.5 star property
    8.8/10 - Excellent (2,253 reviews)
    Return • Oahu (HNL) - Chicago (ORD)
    HNL - ORD • 1 stop ORD - HNL • 1 stop
    NZ$2,106
    NZ$1,830
    per traveller
    found 19 hours ago
    The Godfrey Hotel Chicago
  • Indoor wedding
    Jul 17 - Jul 18

    Swissotel - Chicago + Flight

    Downtown Chicago
    1 night
    4.5 star property
    9.0/10 - Wonderful (3,359 reviews)
    "Staff was so helpful"
    Reviewed May 29, 2026
    Return • Oahu (HNL) - Chicago (ORD)
    HNL - ORD • 1 stop ORD - HNL • 1 stop
    NZ$2,062
    NZ$1,918
    per traveller
    found 19 hours ago
    Swissotel - Chicago
  • Dinner served
    Jul 17 - Jul 18

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    1 night
    4.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    "Great hotel. Loved the lobby and our room. Would definitely stay here again."
    Reviewed May 19, 2026
    Return • Oahu (HNL) - Chicago (ORD)
    HNL - ORD • 1 stop ORD - HNL • 1 stop
    NZ$2,006
    NZ$1,870
    per traveller
    found 19 hours ago
    Kimpton Gray Hotel by IHG
  • Executive lounge
    Jul 17 - Jul 18

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    1 night
    4.5 star property
    8.8/10 - Excellent (2,171 reviews)
    "It had a historic vibe to it but renovated."
    Reviewed May 31, 2026
    Return • Oahu (HNL) - Chicago (ORD)
    HNL - ORD • 1 stop ORD - HNL • 1 stop
    NZ$1,983
    NZ$1,854
    per traveller
    found 19 hours ago
    Fairmont Chicago at Millennium Park
  • Exterior
    Jul 17 - Jul 18

    Arlo Chicago + Flight

    Downtown Chicago
    1 night
    4.0 star property
    9.4/10 - Exceptional (2,115 reviews)
    "Love our stay! Will def stay again!!"
    Reviewed May 29, 2026
    Return • Oahu (HNL) - Chicago (ORD)
    HNL - ORD • 1 stop ORD - HNL • 1 stop
    NZ$2,037
    NZ$1,914
    per traveller
    found 19 hours ago
    Arlo Chicago

Our guide on 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

Our pick of the best Highland Hills Hotel Deals

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 NZ$171 per night from 21 June to 22 June
NZ$171
21 June - 22 June
includes taxes & fees
9/10 Wonderful! (2,775 reviews)
"Orher customers should respect the people next door to them with watching how they close the doors at 2:00/3:00 in the morning"

Reviewed on 31 May 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 NZ$303 per night from 28 June to 29 June
NZ$303
28 June - 29 June
includes taxes & fees
8.8/10 Excellent! (2,597 reviews)
"Convenient to O’Hare with reliable shuttle that runs frequently. The hotel itself and staff exceeded expectations. Would definitely stay here again."

Reviewed on 31 May 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 NZ$383 per night from 28 June to 29 June
NZ$383
28 June - 29 June
includes taxes & fees
9/10 Wonderful! (2,231 reviews)
"It's near the union Station and convenient area, bus stop is near by"

Reviewed on 31 May 2026

Crowne Plaza Chicago West Loop by IHG
See all 3,236 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.

Discover the most popular places to visit in Highland Hills

Wrigley Field

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

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

Naval Base Great Lakes

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
McCormick Place

McCormick Place

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

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.