Holiday Homes in Chicago

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Chicago holiday homes

Exterior

Holiday Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is €177
includes taxes & fees
3 Mar - 4 Mar
A quiet stay while you are away
Exterior detail

Holiday Home in Riverwoods

Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (77 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is €168
includes taxes & fees
3 Mar - 4 Mar
Master qtr close to nature & easy urban facilities
Exterior detail

Holiday Home in Mundelein

Quaint Bungalow, near Great Lakes Naval Base
9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
The price is €283
includes taxes & fees
3 Mar - 4 Mar
Quaint Bungalow, near Great Lakes Naval Base
Interior

Holiday Home in South Shore

Near Lake and Museum • Modern • Game Area
The price is €428
includes taxes & fees
3 Mar - 4 Mar
Near Lake and Museum • Modern • Game Area
Smart TV

Holiday Home in Maywood

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
8.0 out of 10, Very good, (21 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is €258
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Fridge, microwave, oven, stovetop

Holiday Home in Gages Lake

Newly remodeled Near Lake 4BR Hot Tub Navy Family home
10.0 out of 10, Exceptional, (4 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is €647
includes taxes & fees
3 Mar - 4 Mar
Newly remodeled Near Lake 4BR Hot Tub Navy Family home
Outdoor dining

Holiday Home in Wheaton

✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (59 reviews)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is €259
includes taxes & fees
9 Mar - 10 Mar
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining

Holiday Home in Lisle

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
9.4 out of 10, Exceptional, (23 reviews)
"Had a nice time. Great location!"
United States
Jinjer M.
The price is €210
includes taxes & fees
3 Mar - 4 Mar
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Interior

Holiday Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (14 reviews)
"The house was spotless and very comfortable for our needs. Best of all it was not far from our son’s home in River Forest which made going back and forth convenient."
United States
Beryl I.
The price is €396
includes taxes & fees
3 Mar - 4 Mar
Vintage Urban Retreat
Exterior detail

Holiday Home in Oak Park

Oak Park Victorian by FLW Studio
10.0 out of 10, Exceptional, (29 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is €393
includes taxes & fees
3 Mar - 4 Mar
Oak Park Victorian by FLW Studio
Fridge, microwave, oven, stovetop

Holiday Home in Worth

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
9.4 out of 10, Exceptional, (57 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
The price is €287
includes taxes & fees
15 Mar - 16 Mar
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop

Holiday Home in Schaumburg

4BR Near Woodfield Mall & Metra | LCP Collection
8.4 out of 10, Very good, (5 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is €409
includes taxes & fees
3 Mar - 4 Mar
4BR Near Woodfield Mall & Metra | LCP Collection
Dining

Holiday Home in Elmhurst

LUXE 3 BR, 2 BA + Hot Tub
8.8 out of 10, Excellent, (39 reviews)
"Great place to stay. Plenty of backyard space. "
United States
Terrence M.
The price is €316
includes taxes & fees
3 Mar - 4 Mar
LUXE 3 BR, 2 BA + Hot Tub
Fridge, microwave, oven, stovetop

Holiday Home in Westchester

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is €397
includes taxes & fees
8 Mar - 9 Mar
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Private kitchen

Holiday Home in Oakton

Your Next Vacation Home
9.6 out of 10, Exceptional, (63 reviews)
"We enjoyed our stay"
United States
Lukose K.
The price is €239
includes taxes & fees
10 Mar - 11 Mar
Your Next Vacation Home
Dining

Holiday Home in Oak Park

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is €335
includes taxes & fees
30 Mar - 31 Mar
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
TV

Holiday Home in Burbank

Modern 4BR Retreat Near MDW | LCP Collection
8.6 out of 10, Excellent, (7 reviews)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
The price is €383
includes taxes & fees
3 Mar - 4 Mar
Modern 4BR Retreat Near MDW | LCP Collection
Smart TV, fireplace, books, video library

Holiday Home in Skokie

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is €479
includes taxes & fees
3 Mar - 4 Mar
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Private kitchen

Holiday Home in Glen Ellyn

Spacious Deck & Balcony, Game Area, Garage
9.6 out of 10, Exceptional, (20 reviews)
"Great place to stay. "
United States
Jason T.
The price is €398
includes taxes & fees
3 Mar - 4 Mar
Spacious Deck & Balcony, Game Area, Garage
Paper towels, dining tables

Holiday Home in wheaton

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
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 €331
includes taxes & fees
3 Mar - 4 Mar
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"amazing staff and beautiful rooms and lobbies. i just loved the free breakfast"
Carole 1-night trip
Posted 6 hours ago
Hotel Riu Plaza Chicago

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
576
Accommodation
822 Holiday Homes
Lowest Price
€168
Highest Price
€647