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Holiday Homes in Chicago

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chicago holiday homes

A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

1. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (33 reviews)
"Super clean great location short drive to everything we wanted to see!"
United States
eric p.
The price is NZ$999
includes taxes & fees
14 Oct - 15 Oct
ENVITAE Hotel, 4BR Luxury Modern Apartments
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

2. 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
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is NZ$470
includes taxes & fees
27 Oct - 28 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

3. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is NZ$1,139
includes taxes & fees
15 Oct - 16 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is NZ$537
includes taxes & fees
2 Nov - 3 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is NZ$1,876
includes taxes & fees
22 Oct - 23 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
A modern living room with a sectional sofa, a coffee table, and a TV.

6. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is NZ$414
includes taxes & fees
19 Oct - 20 Oct
Attractive Coach House Apartment for rent in Oak Park.
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

7. 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
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is NZ$536
includes taxes & fees
19 Oct - 20 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

8. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (88 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is NZ$366
includes taxes & fees
19 Oct - 20 Oct
Master qtr close to nature & easy urban facilities
Room

9. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is NZ$1,413
includes taxes & fees
14 Oct - 15 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A single-story house with a covered porch, a front door, and a small garden area.

10. 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, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is NZ$615
includes taxes & fees
29 Oct - 30 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

11. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is NZ$642
includes taxes & fees
14 Oct - 15 Oct
LUXE 3 BR, 2 BA + Hot Tub
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

12. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
The price is NZ$1,277
includes taxes & fees
25 Oct - 26 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

13. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is NZ$833
includes taxes & fees
14 Oct - 15 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

14. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (26 reviews)
"We enjoyed our 2 night stay. The home was exactly what we were expecting. It is on a quiet street and is within walking distance to several restaurants. The beds were comfortable and and the lower level bathroom was especially nice to get ready in."
United States
KIM K.
The price is NZ$561
includes taxes & fees
18 Oct - 19 Oct
Cozy Home by O'Hare + EV Plug
A modern kitchen with a marble countertop, stainless steel appliances, and light wood flooring.

15. 3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
The price is NZ$811
includes taxes & fees
2 Nov - 3 Nov
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

16. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is NZ$3,818
includes taxes & fees
26 Oct - 27 Oct
Premier 9BR Art Deco manor with garage.
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

17. Spacious 4BR near Northwestern with King Beds + Crib

Spacious 4BR near Northwestern with King Beds + Crib
Evanston
10.0 out of 10, Exceptional, (5 reviews)
"Spacious home that accommodates all our guests. Very close to Northwestern University so travel was easy! Home was clean and well taken care of. Would definitely recommend to others and would stay agin when I’m in the area."
United States
Melissa C.
The price is NZ$1,323
includes taxes & fees
17 Oct - 18 Oct
Spacious 4BR near Northwestern with King Beds + Crib
A white two-story house with a porch, steps, and a small table with chairs.

18. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is NZ$1,107
includes taxes & fees
14 Oct - 15 Oct
Oak Park Victorian by FLW Studio
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

19. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is NZ$1,776
includes taxes & fees
14 Oct - 15 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A living room with a sofa, a patterned armchair, a coffee table, and a painting on the wall.

20. Cozy Lakeview Home Minutes from O'Hare

Cozy Lakeview Home Minutes from O'Hare
Des Plaines
The price is NZ$868
includes taxes & fees
15 Oct - 16 Oct
Cozy Lakeview Home Minutes from O'Hare
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
"The staff at Gold Club. Mandan geninely treats you like your guest at her own home. We were at the hotel for Chicago Marathon; and their soecial athlete breakfast and attention to details were very helpful."
Ahmad reza 4-night trip
Posted 5 hours ago
Fairmont Chicago at Millennium Park

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
509
Accommodation
773 Holiday Homes
Lowest Price
NZ$366
Highest Price
NZ$3,818