A lake surrounded by autumn-colored trees and a small island with a dock.

Hickory Hills Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Hickory Hills holiday rentals

Individually decorated, individually furnished, iron/ironing board

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
The price is HK$2,039
HK$2,891 total
includes taxes & fees
7 Jul - 8 Jul
Kasa Lake Shore Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,205 reviews)
"Great location"
United States
JAVIER
The price is HK$1,327
HK$1,788 total
includes taxes & fees
8 Jul - 9 Jul
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (499 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is HK$2,252
HK$2,837 total
includes taxes & fees
8 Jul - 9 Jul
Level Chicago – Old Town
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (15 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is HK$1,553
HK$4,133 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$2,078
HK$4,733 total
includes taxes & fees
8 Jul - 9 Jul
River North Rooftop With In and Out Parking 3
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (24 reviews)
"Great location. "
United States
Tom S.
The price is HK$3,404
HK$7,405 total
includes taxes & fees
2 Aug - 3 Aug
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is HK$2,423
HK$5,266 total
includes taxes & fees
16 Jul - 17 Jul
River North Rooftop With In and Out Parking 6
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (24 reviews)
"Great location, close to public transport and Whole Foods. The property was clean, quiet, and easy to access. The host was great with communication. We would stay again! "
United States
Susan R.
The price is HK$9,192
HK$14,933 total
includes taxes & fees
31 Jul - 1 Aug
Spacious 4BR Central Apartment w/ Skyline Views
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is HK$1,573
HK$3,680 total
includes taxes & fees
7 Jul - 8 Jul
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location."
United States
Nicoll M.
The price is HK$1,639
HK$2,195 total
includes taxes & fees
8 Jul - 9 Jul
LIVN Millennium Park Downtown Chicago Superior 2 BR
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (814 reviews)
"Great place to stay."
United States
Benedictine
The price is HK$1,609
HK$2,350 total
includes taxes & fees
7 Jul - 8 Jul
Kasa Magnificent Mile Chicago
Paper towels, dining tables

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
wheaton
10.0 out of 10, Exceptional, (1 review)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
The price is HK$1,878
HK$4,126 total
includes taxes & fees
7 Jul - 8 Jul
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is HK$1,264
HK$2,318 total
includes taxes & fees
27 Jul - 28 Jul
The Oak Park Loft
Games room

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
The price is HK$2,061
HK$6,133 total
includes taxes & fees
13 Jul - 14 Jul
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (30 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is HK$1,071
HK$2,489 total
includes taxes & fees
7 Jul - 8 Jul
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is HK$2,965
HK$5,972 total
includes taxes & fees
17 Jul - 18 Jul
South Loop Rooftop With In and Out Parking 2
Interior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
The price is HK$5,796
HK$10,152 total
includes taxes & fees
18 Jul - 19 Jul
Modern 3BR Apartment Near North Ave Shops
Fridge, microwave, oven, stovetop

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (11 reviews)
"Amazing property had everything we need! "
United States
Rachel
The price is HK$1,588
HK$3,259 total
includes taxes & fees
7 Jul - 8 Jul
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is HK$3,804
HK$7,191 total
includes taxes & fees
29 Jul - 30 Jul
Downtown Chicago Stay with Free In & Out Parking 5
Interior

King Bed Suite, *Spacious Newly Remodeled House*

King Bed Suite, *Spacious Newly Remodeled House*
Joliet
10.0 out of 10, Exceptional, (50 reviews)
"The place was everything we needed , clean, convenient and comfortable "
United States
Victor P.
The price is HK$1,588
HK$3,124 total
includes taxes & fees
7 Jul - 8 Jul
King Bed Suite, *Spacious Newly Remodeled House*
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.
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Top Hickory Hills Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Clean high floor room with a city/lake view helpful staff and housekeeping. I will stay here again in the future."
Merttay 2-night trip
Posted 2 hours ago
Hyatt Regency Chicago

Find out more about Hickory Hills

Search for holiday rentals in Hickory Hills on Expedia! You can easily find your home rentals, villas, holiday apartments in Hickory Hills using one of the methods below:

  • View our selection of featured holiday rentals in Hickory Hills
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  • Enter your travel dates to view the best deals on holiday rentals in Hickory Hills while they last

Look no further and take a look at our great range of rental properties in Hickory Hills!

Frequently asked questions

Can I find a holiday rental in Hickory Hills?

Yes, there are holiday rentals close to the most popular sights in Hickory Hills, or you can select a more secluded option if you're looking for a relaxing stay. Hickory Hills is known for its shopping and forests. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Hickory Hills has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Hickory Hills is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Hickory Hills?

Explore the area and family-friendly sights such as Galloping Ghost, or get out into nature at a spot like Grant Park. In the wider area, you’ll find popular places such as United Center and Soldier Field.

What’s a holiday rental in Hickory Hills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hickory Hills. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.