Holiday Homes in Chicago

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Chicago holiday homes

Exterior

Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
The price is NZ$778
includes taxes & fees
13 May - 14 May
Envitae Hotel, 4BR Modern Sleek Apartment
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, (79 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
The price is NZ$329
includes taxes & fees
28 Apr - 29 Apr
Master qtr close to nature & easy urban facilities
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 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 NZ$410
includes taxes & fees
21 Apr - 22 Apr
A quiet stay while you are away
Exterior detail

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"The home was a perfect spot for our family while we visited extended family. Quaint home and matched what was advertised online."
United States
Kayla C.
The price is NZ$553
includes taxes & fees
19 Apr - 20 Apr
Quaint Bungalow, near Great Lakes Naval Base
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is NZ$968
includes taxes & fees
28 Apr - 29 Apr
Near Lake and Museum • Modern • Game Area
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (59 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is NZ$567
includes taxes & fees
13 May - 14 May
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Carol Stream
9.6 out of 10, Exceptional, (4 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is NZ$864
includes taxes & fees
22 Apr - 23 Apr
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Fridge, microwave, oven, stovetop

Navy Family home -Near Lake 4BR Hot Tub

Navy Family home -Near Lake 4BR Hot Tub
Gages Lake
10.0 out of 10, Exceptional, (8 reviews)
"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 NZ$784
includes taxes & fees
19 Apr - 20 Apr
Navy Family home -Near Lake 4BR Hot Tub
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (62 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is NZ$524
includes taxes & fees
21 Apr - 22 Apr
✽ Charming Cottage ✽ close to College/Town/Station
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (41 reviews)
"Nice place, alot of space. Great host"
United States
Devonta J.
The price is NZ$459
includes taxes & fees
16 Apr - 17 Apr
LUXE 3 BR, 2 BA + Hot Tub
Smart TV

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (23 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 NZ$507
includes taxes & fees
28 Apr - 29 Apr
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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, (27 reviews)
"Had a nice time. Great location!"
United States
Jinjer M.
The price is NZ$430
includes taxes & fees
16 Apr - 17 Apr
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Dining

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

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is NZ$510
includes taxes & fees
27 Apr - 28 Apr
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
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 NZ$862
includes taxes & fees
21 Apr - 22 Apr
Vintage Urban Retreat
Fridge, microwave, oven, stovetop

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
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 NZ$852
includes taxes & fees
20 Apr - 21 Apr
4BR Near Woodfield Mall & Metra | LCP Collection
Fridge, microwave, oven, stovetop

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
Berwyn
10.0 out of 10, Exceptional, (2 reviews)
"We had an excellent stay. Our host was responsive & accommodated an extremely early check-in request for us. This helped tremendously. Instructions were clear to get in & the home was spacious & clean. The location was great & easily accessible to restaurants. We would stay here again. "
United States
Sarah H.
The price is NZ$532
includes taxes & fees
21 Apr - 22 Apr
Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
Smart TV, fireplace, offices

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is NZ$699
includes taxes & fees
16 Apr - 17 Apr
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (71 reviews)
"Hist was welcoming!House clean and well taken care of!"
United States
Edward H.
The price is NZ$567
includes taxes & fees
21 Apr - 22 Apr
Your Next Vacation Home
Living area

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
10.0 out of 10, Exceptional, (1 review)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is NZ$356
includes taxes & fees
20 Apr - 21 Apr
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Fridge, microwave, oven, stovetop

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Bensenville
10.0 out of 10, Exceptional, (1 review)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is NZ$1,007
includes taxes & fees
20 Apr - 21 Apr
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Nice hotel I would stay here again"
Samentha 3-night trip
Posted 1 hour ago
Fairmont Chicago at Millennium Park

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
429
Accommodation
793 Holiday Homes
Lowest Price
NZ$329
Highest Price
NZ$1,007