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Holiday Homes in Chicago

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chicago holiday homes

Property grounds

1. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
The price is €890
includes taxes & fees
16 Sept - 17 Sept
ENVITAE Hotel, 4BR Luxury Modern Apartments
Living area

2. Scott C.H. - Chicago Getaway

Scott C.H. - Chicago Getaway
Near North Side
The price is €1,070
includes taxes & fees
31 Aug - 1 Sept
Scott C.H. - Chicago Getaway
Living area

3. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (4 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is €471
includes taxes & fees
31 Aug - 1 Sept
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Interior

4. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.6 out of 10, Exceptional, (4 reviews)
"Really enjoyed staying at this property! Clean and safe. Would recommend!"
United States
Emmeline R.
The price is €1,118
includes taxes & fees
18 Sept - 19 Sept
Modern 3BR Apartment Near North Ave Shops
Dining

5. 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!
Room

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

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is €607
includes taxes & fees
31 Aug - 1 Sept
Arcade • Theater • Gym • Office • Sleeps 15
Private kitchen

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
The price is €386
includes taxes & fees
31 Aug - 1 Sept
Game Room • Fire-pit • Playground • Gym • Billiard
Exterior

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, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is €311
includes taxes & fees
29 Sept - 30 Sept
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Exterior detail

9. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (86 reviews)
"Lovely, quiet property with easy access to retail & restaurants. Perfect for a long weekend away."
United States
Suzanne H.
The price is €184
includes taxes & fees
7 Sept - 8 Sept
Master qtr close to nature & easy urban facilities
Living area

10. 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, (33 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is €264
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Dining

11. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (55 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is €329
includes taxes & fees
2 Sept - 3 Sept
LUXE 3 BR, 2 BA + Hot Tub
Dining

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (6 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 €720
includes taxes & fees
8 Sept - 9 Sept
Sleeps 18 • 8BR • Game Room • Gym • Theater
Private kitchen

13. 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
9.4 out of 10, Exceptional, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is €358
includes taxes & fees
31 Aug - 1 Sept
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Room

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €319
includes taxes & fees
13 Sept - 14 Sept
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Interior

15. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (21 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is €293
includes taxes & fees
1 Sept - 2 Sept
Cozy Home by O'Hare + EV Plug
Exterior detail

16. 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 €438
includes taxes & fees
31 Aug - 1 Sept
Oak Park Victorian by FLW Studio
Private kitchen

17. 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 €403
includes taxes & fees
8 Sept - 9 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
Living area

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

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.0 out of 10, Very good, (3 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
Attractive Coach House Apartment for rent in Oak Park.
Exterior

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

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (70 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is €286
includes taxes & fees
6 Sept - 7 Sept
✽ Charming Cottage ✽ close to College/Town/Station
Terrace/patio

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

Sleeps 18 • 7BR • Gym • Game Room • Theater
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
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

Hilton Chicago

10/10 Excellent
"The hotel was exceptionally beautifully and the staff were so friendly and helpful. We were there for the BTS concert and the hotel went out of their way to make the space welcoming to Army (fans) by setting up a designated spot for photo ops and meet ups! They also played BTS music in the lobby to help foster a fun and exciting atmosphere. Besides the electric atmosphere, the hotel itself was comfortable with many amenities available. The rooms were spacious clean. It was centrally located and we were walking distance to many restaurants and tourist sites. It was my first time in Chicago and when I go back for a visit, the Hilton Chicago will be my first choice for accommodations"
Odelia 3-night trip
Posted 1 hour ago
Hilton Chicago

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
284
Accommodation
792 Holiday Homes
Lowest Price
€184
Highest Price
€1,118