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

Hickory Hills Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Hickory Hills vacation rentals

Lake

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
The price is SAR 947
SAR 1,349 total
includes taxes & fees
9 Aug - 10 Aug
Kasa Lake Shore Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,208 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is SAR 718
SAR 953 total
includes taxes & fees
9 Aug - 10 Aug
Sentral Michigan Avenue
Full-size 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 SAR 1,315
SAR 1,636 total
includes taxes & fees
9 Aug - 10 Aug
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, (16 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is SAR 3,976
SAR 6,552 total
includes taxes & fees
30 Jul - 31 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)
The price is SAR 995
SAR 2,284 total
includes taxes & fees
26 Jul - 27 Jul
River North Rooftop With In and Out Parking 3
Exterior detail

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 SAR 1,648
SAR 3,587 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.
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, (26 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.
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.
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
9.2 out of 10, Wonderful, (5 reviews)
The price is SAR 1,048
SAR 1,411 total
includes taxes & fees
12 Jul - 13 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, (816 reviews)
"Great place to stay."
United States
Benedictine
The price is SAR 1,096
SAR 1,507 total
includes taxes & fees
21 Jul - 22 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 SAR 1,116
SAR 2,209 total
includes taxes & fees
14 Jul - 15 Jul
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
Design Apartment, Private Bathroom (The Oak Park Loft) | 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 SAR 605
SAR 1,110 total
includes taxes & fees
13 Jul - 14 Jul
The Oak Park Loft
TV

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

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
The price is SAR 838
SAR 2,732 total
includes taxes & fees
14 Jul - 15 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 SAR 765
SAR 1,487 total
includes taxes & fees
14 Jul - 15 Jul
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Interior

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 SAR 1,393
SAR 2,822 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)
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 SAR 845
SAR 1,650 total
includes taxes & fees
12 Jul - 13 Jul
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Exterior

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.
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, (51 reviews)
"The place was everything we needed , clean, convenient and comfortable "
United States
Victor P.
The price is SAR 791
SAR 1,535 total
includes taxes & fees
12 Jul - 13 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hickory Hills Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Great location, welcoming staff, comfortable room"
Nick 2-night trip
Posted less than an hour ago
River Hotel

Frequently asked questions

Can I find a vacation rental in Hickory Hills?

Yes, there are vacation rentals near popular attractions in Hickory Hills, or you can choose a more secluded option if you're looking for relaxation. 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 vacation rentals that Hickory Hills has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Hickory Hills is located in the city center and has a balcony, a barbecue grill, 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 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 Childrens Museum of Oak Lawn, or get out into nature at a spot like Grant Park. In the larger area, you’ll find popular places like United Center and Soldier Field.

What’s a vacation rental in Hickory Hills like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Hickory Hills. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for small groups.