Highland Park Holiday Packages

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So what's the secret? Simple, we can combine your flights and hotels into one neat little package.

Your Highland Park vacation is about to get a whole lot more exciting.

You might even see savings of up to . Also, with more than 550 airlines and 665,000 worldwide properties, it's easy to craft your dream holiday.

Wotif boasts some of the most attractive deals under the sun. Start packing — now's the perfect time to begin a new adventure.

Highland Park Accommodation

Even though there are no accommodations in central Highland Park, you'll be delighted to discover that there are 20 properties on offer just a little further afield.

There are always stacks of things to get ready before a holiday. Why not let us take the heat off by pointing you in the direction of some terrific places? We think The Deer Path Inn (255 East Illinois Road) and The Glen Club (2901 West Lake Avenue) are fantastic options.

Car Hire in Highland Park

If you're landing at O'Hare International Airport, check out the deals at Thrifty Car Rental or Dollar Rent A Car. There's no need to mess around with airport shuttles or pricey taxis — their offices are just an easy stroll from the baggage claim.

You won't have any problems hiring a vehicle in the heart of the city, even if you're fussy. See if something grabs your attention at Enterprise (1430 Old Skokie Valley Road). Otherwise, head over to Budget (1333 Park Ave W) and investigate their offerings.

Holidays to Highland Park

Hoping to scratch your travel itch in Highland Park? We don't blame you. But before you make your way to this spectacular destination, why not spend a bit of time getting to know the essentials?

To reach this Chicago neighbourhood, you'll need to venture 35 kilometres northwest of the city centre.

If you've heard your travel pals not only rave about Highland Park but about Chicago in general, then you won't be at all surprised to learn that approximately 2 700 000 people call it home.

Top Highland Park hotels

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 AU$270 per night from 18 May to 19 May
AU$270
includes taxes & fees
18 May - 19 May
Hyatt Regency O'Hare Chicago: Eco-certified hotel with free WiFi and a bar/lounge. Located in the entertainment district.
"All around great."

Reviewed on 30 Apr. 2025

Hyatt Regency O'Hare Chicago
Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$311 per night from 6 May to 7 May
AU$311
includes taxes & fees
6 May - 7 May
Claridge House: Pet-friendly hotel with a bar/lounge and a coffee shop/cafe. Located in the city centre.
"What I really like is that it was walkable to many places. Good location."

Reviewed on 1 May 2025

Claridge House
Ambassador Hotel Chicago

Ambassador Hotel Chicago

4 out of 5
1301 N State Pkwy, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$274 per night from 4 May to 5 May
AU$274
includes taxes & fees
4 May - 5 May
The Chicago Hotel Collection Ambassador Gold Coast: Pet-friendly hotel with free WiFi and a bar/lounge. Located near a train station.
"We stayed for 4days/3nights. We were given a free King bed upgrade upon arrival. We were also given free breakfast and bar drinks vouchers for each day or our stay. Pretty good (free food). Very lovely/safe area. Took many late night walks around the area and 3-4 blocks down to Lake Shore Drive waterfront. ..."

Reviewed on 30 Apr. 2025

Ambassador Hotel Chicago
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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.