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Holiday Homes in Central Chicago

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Central Chicago holiday homes

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

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is NZ$640
includes taxes & fees
27 Sept - 28 Sept
Cozy Studio Suite, Steps from River North & Shops
A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

2. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
The price is NZ$1,121
includes taxes & fees
28 Sept - 29 Sept
Envitae Hotel, 4BR Modern Sleek Apartment
A billiards room with multiple tables, large windows, and a high ceiling with exposed ductwork.

3. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is NZ$1,626
includes taxes & fees
8 Oct - 9 Oct
Wabash 4BR - Pool, Free In & Out Parking 1
A modern gym with various exercise equipment, including a bench press, dumbbells, and a treadmill.

4. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is NZ$7,090
includes taxes & fees
13 Oct - 14 Oct
Brand New 12 Bedroom Mansion

5. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.8 out of 10, Exceptional, (6 reviews)
Modern 3BR Apartment Near North Ave Shops

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is NZ$959
includes taxes & fees
24 Sept - 25 Sept
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.

7. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is NZ$1,226
includes taxes & fees
29 Sept - 30 Sept
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

8. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
The price is NZ$502
includes taxes & fees
12 Oct - 13 Oct
A quiet stay while you are away

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$1,267
includes taxes & fees
30 Sept - 1 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

10. 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, (43 reviews)
"We had a really nice stay at the Village Inn. We appreciated that artistic furnishings and decorations, and the thoughtful touches throughout. (We are a white noise family, so we were very happy to find a white noise machine in every bedroom!)The neighborhood is very quiet and also close to great shops and restaurants as well as the train. We enjoyed being able to walk to dinner in the evening, and walk to the train to take a short ride right to the Art Institute. The kitchen was great for...
United States
Andrea M.
The price is NZ$1,289
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

11. 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)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is NZ$529
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a sectional sofa, a coffee table, and a TV.

12. 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$400
includes taxes & fees
13 Oct - 14 Oct
Attractive Coach House Apartment for rent in Oak Park.
A single-story house with a covered porch, a front door, and a small garden area.

13. 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$595
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A white two-story house with a porch, steps, and a small table with chairs.

14. 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$991
includes taxes & fees
29 Sept - 30 Sept
Oak Park Victorian by FLW Studio
A circular fire pit with chairs around it, string lights overhead, and a house in the background.

15. 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.
The price is NZ$1,641
includes taxes & fees
30 Sept - 1 Oct
Sleeps 18 • 7BR • Gym • Game Room • Theater
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

16. 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, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is NZ$1,607
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A wooden deck with a railing, a staircase, and a window with a wreath.

17. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (35 reviews)
"I had a fun stay "
United States
Jusu K.
The price is NZ$363
includes taxes & fees
29 Sept - 30 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

18. 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$846
includes taxes & fees
30 Sept - 1 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.

19. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (23 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 NZ$543
includes taxes & fees
27 Sept - 28 Sept
Cozy Home by O'Hare + EV Plug
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

20. 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$367
includes taxes & fees
30 Sept - 1 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and 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 Central Chicago Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Hotel best feature was Location!!!"
Shirley 5-night trip
Posted 5 hours ago
Hotel Saint Clair- Magnificent Mile

Find out more about Central Chicago

Central Chicago Holiday Homes information

Number of reviews
354
Accommodation
29 Holiday Homes
Lowest Price
NZ$363
Highest Price
NZ$1,641

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