Holiday Homes in Chicago

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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Chicago holiday homes

Fridge, microwave, oven, stovetop

Newly remodeled-Near Lake 4BR w/ Hot Tub & Games

Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
2.0 star property
Gages Lake
10.0 out of 10, Exceptional, (1 review)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
The price is €467
includes taxes & fees
18 Jan - 19 Jan
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
Dining

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
2.0 star property
Portage Park
The price is €665
includes taxes & fees
15 Jan - 16 Jan
Sleeps 18 • 8BR • Game Room • Gym • Theater
Interior

Near Lake and Museum • Pool Table • Game Area

Near Lake and Museum • Pool Table • Game Area
2.0 star property
South Shore
The price is €401
includes taxes & fees
19 Jan - 20 Jan
Near Lake and Museum • Pool Table • Game Area
2 bedrooms, iron/ironing board, WiFi, bed sheets

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €248
includes taxes & fees
18 Jan - 19 Jan
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Fridge, microwave, oven, stovetop

Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
2.0 star property
Belmont Cragin
Game Room • Fire-pit • Playground • Gym • Billiard
Fridge, microwave, stovetop, dishwasher

Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
2.0 star property
Forest Park
The price is €365
includes taxes & fees
18 Jan - 19 Jan
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exterior detail

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (68 reviews)
"Super cozy!! The neighborhood is so so so lovely! "
United States
Andrea M.
The price is €289
includes taxes & fees
18 Jan - 19 Jan
Quaint Bungalow, near Great Lakes Naval Base
2 bedrooms, iron/ironing board, WiFi, bed sheets

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
La Grange Highlands
10.0 out of 10, Exceptional, (2 reviews)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
The price is €224
includes taxes & fees
15 Jan - 16 Jan
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
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, (20 reviews)
"Had a nice time. Great location!"
United States
Jinjer M.
The price is €223
includes taxes & fees
15 Jan - 16 Jan
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Fridge, microwave, oven, stovetop

Gated Family Home w/ Chef’s Kitchen

Gated Family Home w/ Chef’s Kitchen
2.0 star property
Humboldt Park
The price is €415
includes taxes & fees
15 Jan - 16 Jan
Gated Family Home w/ Chef’s Kitchen
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, (19 reviews)
"Great place Great location "
United States
Josh W.
The price is €391
includes taxes & fees
20 Jan - 21 Jan
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Dining

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
2.0 star property
Oak Park
The price is €210
includes taxes & fees
20 Jan - 21 Jan
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Paper towels, dining tables

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
streamwood
10.0 out of 10, Exceptional, (2 reviews)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is €311
includes taxes & fees
15 Jan - 16 Jan
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (76 reviews)
"Amazing area, loved the feel of it all and very quiet neighborhood."
United States
Joshua K.
The price is €170
includes taxes & fees
19 Jan - 20 Jan
Master qtr close to nature & easy urban facilities
Fridge, microwave, oven, stovetop

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
2.0 star property
Homewood
Modern Stylish Comfort Near Casino and Hwy
Microwave, oven, stovetop, dishwasher

Home -2 bedroom, 4k projector

Home -2 bedroom, 4k projector
2.0 star property
Waukegan
8.8 out of 10, Excellent, (3 reviews)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
The price is €232
includes taxes & fees
12 Feb - 13 Feb
Home -2 bedroom, 4k projector
Smart TV, offices

North Chi retreatNavySaunaTiki BarGames

North Chi retreatNavySaunaTiki BarGames
North Chicago
9.8 out of 10, Exceptional, (18 reviews)
"Nice clean home, easy check in processes close to the base. Perfect for our stay with kids. "
United States
Thomas D.
The price is €457
includes taxes & fees
19 Jan - 20 Jan
North Chi retreatNavySaunaTiki BarGames
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is €454
includes taxes & fees
21 Jan - 22 Jan
Vintage Urban Retreat
Interior

Luxury Suite in Glen Ellyn, IL USA

Luxury Suite in Glen Ellyn, IL USA
Glen Ellyn
9.6 out of 10, Exceptional, (10 reviews)
"Was very comfortable. Had everything we needed except wash clothes. Walmart really close. "
United States
Debra B.
Luxury Suite in Glen Ellyn, IL USA
Terrace/patio

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
2.0 star property
Austin
The price is €981
includes taxes & fees
27 Jan - 28 Jan
Sleeps 18 • 7BR • Gym • Game Room • Theater
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 Chicago Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"10/10"
Ivan 1-night trip
Posted 18 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
229
Accommodation
822 Holiday Homes
Lowest Price
€170
Highest Price
€981