Photo by Phil Ostroff

Holiday Homes in Central Chicago

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Central Chicago holiday homes

A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

1. 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 €459
includes taxes & fees
8 Nov - 9 Nov
Envitae Hotel, 4BR Modern Sleek Apartment
A kitchen with a white countertop, dark wooden stools, and a window with decorative iron bars.

2. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
9.0 out of 10, Wonderful, (2 reviews)
"Property is a bit worn, however, furnishings are in good shape and nicely appointed for our stay. Clean upon arrival and great location for an extended stay in Chicago. Host has extra supplies that are helpful- umbrellas, games, laundry detergent that made our stay easier and more enjoyable. Would stay again."
United States
Sara C.
The price is €613
includes taxes & fees
9 Nov - 10 Nov
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is €777
includes taxes & fees
17 Nov - 18 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

4. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is €519
includes taxes & fees
19 Nov - 20 Nov
Chicago Riverhouse with private fenced in oasis
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

5. 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)
"Great location. Great place to stay. "
United States
Jill L.
The price is €519
includes taxes & fees
16 Nov - 17 Nov
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern living room with a white sofa, a white armchair, and a floor lamp.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is €424
includes taxes & fees
9 Nov - 10 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

7. 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 €534
includes taxes & fees
9 Nov - 10 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
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.
The price is €371
includes taxes & fees
23 Nov - 24 Nov
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

9. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
The price is €331
includes taxes & fees
12 Nov - 13 Nov
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

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, (35 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is €264
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

11. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
Brookfield
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
The price is €379
includes taxes & fees
9 Nov - 10 Nov
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

12. 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 €1,558
includes taxes & fees
16 Nov - 17 Nov
Premier 9BR Art Deco manor with garage.
A cozy outdoor seating area with Adirondack chairs around a fire pit, string lights overhead, and a house in the background.

13. Firepit • Game Room • Theater • Gym • Sleeps 18

Firepit • Game Room • Theater • Gym • Sleeps 18
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 €803
includes taxes & fees
9 Nov - 10 Nov
Firepit • Game Room • Theater • Gym • Sleeps 18
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
10.0 out of 10, Exceptional, (1 review)
"Happy with communication, comfort and location"
United States
Kelly K.
The price is €265
includes taxes & fees
1 Dec - 2 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

15. 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 €398
includes taxes & fees
9 Nov - 10 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

16. 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
9.6 out of 10, Exceptional, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €223
includes taxes & fees
9 Nov - 10 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
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, (37 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €171
includes taxes & fees
9 Nov - 10 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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 €493
includes taxes & fees
10 Nov - 11 Nov
Oak Park Victorian by FLW Studio
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

19. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is €577
includes taxes & fees
9 Nov - 10 Nov
Vibrant House, Walk to Train, Game Room
A modern dining area with a round table, black chairs, and a hanging light fixture.

20. Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston

Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston
South Evanston
8.8 out of 10, Excellent, (9 reviews)
"Great place everything was clean, good communication from host. Perfect space!"
United States
Shelly S.
The price is €724
includes taxes & fees
17 Nov - 18 Nov
Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston
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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Learn more about Central Chicago

Discover the local area in Central Chicago as you check out popular sights like Navy Pier and Soldier Field.

See all hotels in Central Chicago
A city skyline at dusk with illuminated buildings reflecting on the water.
Photo by Phil Ostroff
Open Photo by Phil Ostroff

Top reviews in Central Chicago

A modern hotel lobby with a spiral staircase, seating areas, and large windows offering city views.
Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
Downtown Chicago

10/10 Excellent

Location, staff and the room.
Ireland
Beechom
Reviewed November 9, 2025
Residence Inn Chicago Downtown Magnificent Mile

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