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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

Communal lounging

1. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.0 out of 10, Wonderful, (4 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is €359
includes taxes & fees
15 Oct - 16 Oct
Cozy Studio Suite, Steps from River North & Shops
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

2. 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 €496
includes taxes & fees
15 Oct - 16 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

3. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A modern living room with a sectional sofa, a coffee table, and a TV.

4. 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 €209
includes taxes & fees
28 Oct - 29 Oct
Attractive Coach House Apartment for rent in Oak Park.
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €275
includes taxes & fees
9 Nov - 10 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

6. 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.
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

7. 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 €956
includes taxes & fees
22 Oct - 23 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
A single-story house with a covered porch, a front door, and a small garden area.

8. 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.
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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 €815
includes taxes & fees
21 Oct - 22 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

10. 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 €191
includes taxes & fees
19 Oct - 20 Oct
Master qtr close to nature & easy urban facilities
A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

11. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Near South Side
9.0 out of 10, Wonderful, (6 reviews)
"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"
United States
Ilir T.
The price is €669
includes taxes & fees
21 Oct - 22 Oct
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

12. 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 €279
includes taxes & fees
28 Oct - 29 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

13. 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 €250
includes taxes & fees
27 Oct - 28 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

14. 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 €445
includes taxes & fees
28 Oct - 29 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

15. 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 €342
includes taxes & fees
28 Oct - 29 Oct
LUXE 3 BR, 2 BA + Hot Tub
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

16. 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.
Cozy Home by O'Hare + EV Plug
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.
Spacious 4BR near Northwestern with King Beds + Crib
A two-story house with a garage, solar panels, and a red car parked in front.

18. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is €358
includes taxes & fees
19 Oct - 20 Oct
Lombard 1BR & 1BH Suite Close to freeway & Mall
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

19. 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 €2,065
includes taxes & fees
27 Oct - 28 Oct
Premier 9BR Art Deco manor with garage.
A building with a sign reading 'Hale Street Cantina' and a brick facade.

20. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (74 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is €296
includes taxes & fees
2 Nov - 3 Nov
✽ Charming Cottage ✽ close to College/Town/Station
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

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

10/10 Excellent
"Amazing locations and staff!"
Sarah 2-night trip
Posted 10 hours ago
The Godfrey Hotel Chicago

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
334
Accommodation
744 Holiday Homes
Lowest Price
€191
Highest Price
€2,065