Chicago Holiday House Rentals from AU$293: Search Holiday Homes

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Our top choices for Chicago holiday homes

A modern bathroom with a large mirror, a sink, and two hanging planters with greenery.

A dining area with a dark wooden table, six chairs, a coffee machine, and a potted plant.

A living room with a dark wood floor, a black sofa, a round coffee table, and a black cabinet with a mirror.

A modern kitchen with white cabinets, a granite countertop, a coffee machine, and a window with blinds.

1. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

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

Lincoln Park

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"This VRBO was perfect for our group! There was more than enough space. The host let us drop our luggage off early since we arrived in the area before 4. The listing initially had errors, but the host updated the listing and we knew what to expect coming into it. Thank you for a wonderful stay!"

Jamiee B.

The price is AU$924

AU$924

includes taxes & fees

1 Nov - 2 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.

A white arched cabinet with glass doors, containing kitchen appliances like a blender, toaster, and kettle.

A modern living room with a white sofa, a round coffee table, a fireplace, and a flat-screen TV mounted on the wall.

A room with a black bean bag chair, a small table with a plant, and a tic-tac-toe game on a clear glass table.

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

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

Portage Park

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Wonderful night, boys loved the arcade area."

Anonymous traveller

The price is AU$1,297

AU$1,297

includes taxes & fees

3 Nov - 4 Nov

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

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

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)

10/10

Exceptional

(7 reviews)

"Great location, safe and quiet. Perfect for our family of 6!"

Jason

The price is AU$798

AU$798

includes taxes & fees

2 Nov - 3 Nov

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

A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

A modern hallway with a glass door, a round mirror, a wooden bench, and a cactus plant.

A modern living room with a sofa, coffee table, and large windows.

A modern kitchen with a central island, built-in appliances, and a dining area with a view.

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)

10/10

Exceptional

(45 reviews)

"House was perfect for our needs and all as described per the listing."

Robert S.

The price is AU$842

AU$842

includes taxes & fees

1 Nov - 2 Nov

Chicago Riverhouse with private fenced in oasis

A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

A modern living room with a sofa, coffee table, and a dining area with blue chairs.

A dining area with a round table, blue velvet chairs, and a gold chandelier.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

5. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room

Brookfield

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Wonderful place to stay!"

Chasity D.

The price is AU$993

AU$993

includes taxes & fees

9 Nov - 10 Nov

Vibrant House, Walk to Train, Game Room

A modern living room with a dining area, a sofa set, and a television mounted on the wall.

A modern living room with a sofa, a coffee table, and a television mounted on the wall.

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

Arcade • Theater • Gym • Office • Sleeps 15

Portage Park

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"Good place for a large group or family."

Daniel J.

The price is AU$1,103

AU$1,103

includes taxes & fees

3 Nov - 4 Nov

Arcade • Theater • Gym • Office • Sleeps 15

A cozy living room with a neon sign, a fireplace, a television, and a guitar.

A covered outdoor area with wooden flooring, a green bench, a small table, and a potted plant.

A spacious living area with a sofa, a dining table, and a kitchen in the background.

A cozy interior with a neon sign reading "The Village Inn," brick walls, a marble table, and comfortable seating.

7. 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)

9.6/10

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."

Alison G.

The price is AU$938

AU$938

includes taxes & fees

10 Nov - 11 Nov

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

A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

A laundry room with a front-loading washing machine, a dryer, and a small sink.

A kitchen with wooden cabinets, a stainless steel stove, a microwave, and a refrigerator.

A living room with a black leather sofa, two blue armchairs, a coffee table, and a floral rug.

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

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

Westmont

The price is AU$411

AU$411

includes taxes & fees

2 Nov - 3 Nov

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

A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and pendant lighting.

A modern living room with a white sofa, a white armchair, and a floor lamp.

A modern living room with a fireplace, two white sofas, a coffee table, and a pool table.

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

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

Belmont Cragin

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Everyone was super happy with the house and the location."

Rhiannon

The price is AU$778

AU$778

includes taxes & fees

3 Nov - 4 Nov

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

A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

A living room with a brown sofa, a beige ottoman, and a red vase. There are three framed pictures on the wall and a window with blinds.

A spacious living room with a large sectional sofa, a coffee table, and a kitchen area with a refrigerator and cabinets.

A kitchen with wooden cabinets, stainless steel appliances, a dining table with chairs, and a patterned rug.

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)

7.8/10

Good

(35 reviews)

"Very nice home with basement bar. Host was very accommodating."

Carl T.

The price is AU$425

AU$425

includes taxes & fees

3 Nov - 4 Nov

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

A single-story house with a covered porch, a front door, and a small garden area.

A kitchen with a coffee maker, a stove, and a window.

A living room with a ceiling fan, a sofa, a coffee table, and two blue chairs.

A staircase leading to a porch with a 'WELCOME' sign.

11. 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)

10/10

Exceptional

(4 reviews)

"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."

Willow M.

The price is AU$540

AU$540

includes taxes & fees

3 Nov - 4 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.

A room with a desk, chair, computer, lamp, and potted plants.

A living room with a flat-screen TV, a blue sofa, a wooden coffee table, and a dining area with a table and chairs.

A courtyard with a picnic table and benches, surrounded by brick buildings with multiple windows.

12. 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 AU$530

AU$530

includes taxes & fees

30 Oct - 31 Oct

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

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

A modern kitchen with white cabinets, a stainless steel refrigerator, a black stove, a microwave, and a dishwasher.

A single-story house with a front door, two windows, and a small porch.

A bedroom with a bed, bedside tables, a ceiling fan, a window with blinds, a mirror, and a wardrobe.

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

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"This property fully met our needs for our weekend trip to the Chicagoland area to visit family in Westmont and explore the city. Finding an affordable, conveniently located, and pet friendly location was a major concern on this trip…finding this property relieved all of our concerns."

Chad R.

The price is AU$383

AU$383

includes taxes & fees

9 Nov - 10 Nov

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.

A dining area with a wooden table, four chairs, a sofa, and a lamp.

A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

A living room with a sofa, a coffee table, and a TV mounted on the wall.

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)

10/10

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."

LEM R.

The price is AU$667

AU$667

includes taxes & fees

1 Nov - 2 Nov

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.

A living room with a glass coffee table, a gray sofa, and a patterned rug.

A neatly arranged bedroom with a bed, bedside tables, a mirror, and a ceiling fan.

A living room with a glass coffee table, a potted plant, a flat-screen TV, a dining table with chairs, and a clock on the wall.

15. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

8.6 out of 10, Excellent, (64 reviews)

8.6/10

Excellent

(64 reviews)

"We had a wonderful stay"

Anonymous traveller

The price is AU$518

AU$518

includes taxes & fees

2 Nov - 3 Nov

LUXE 3 BR, 2 BA + Hot Tub

A modern living room with a grey sofa, a white armchair, a coffee table, and a TV. There is a kitchen area in the background with a dining table and chairs.

A backyard patio with wicker furniture, a barbecue grill, and string lights.

A modern kitchen with stainless steel appliances, a dining area with blue tableware, and a cityscape painting on the wall.

A bedroom with a large bed, two bedside tables, a wall-mounted artwork, and a window with curtains.

16. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Highland Hills

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"I booked this property because I was told (before I made the reservation) that the bedroom and one of the bathrooms were on the main floor. I specifically inquired whether my mother-in-law would need to use stairs to access a bedroom and bathroom. In the words of the host, "the main living area, kitchen, two bedrooms and a full bathroom are on the main floor. Only the basement requires the use of steps ". This was not the case. The two bedrooms and a full bathroom are up a flight of 5...

Denise G.

The price is AU$551

AU$551

includes taxes & fees

18 Nov - 19 Nov

Cozy Home | King Bed | 10P | Metra |Chicago Suburb

A modern kitchen with a marble countertop, stainless steel appliances, and light wood flooring.

A dining area with a dark wooden table, white chairs, a bench, and a TV mounted on the wall.

A modern kitchen with a central island, dark wooden dining table, and a ceiling fan.

A bedroom with two beds, a ceiling fan, and a door.

17. 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 AU$585

AU$585

includes taxes & fees

9 Nov - 10 Nov

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

A modern building with a large dome and circular design, surrounded by a landscaped area with trees and a water body.

A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

A modern living room with a green wall, a leather sofa, a round coffee table, and a chandelier.

A bedroom with a bed, bedside table, desk, and a window with curtains.

18. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.

Lakeview

7.4 out of 10, Good, (3 reviews)

7.4/10

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. "

Joel D.

The price is AU$2,545

AU$2,545

includes taxes & fees

2 Nov - 3 Nov

Premier 9BR Art Deco manor with garage.

A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

A hanging flower basket with purple flowers, a brick wall, and a green lawn with trees in the background.

A large bed with a wooden headboard, two bedside tables with lamps, and a window with a view of trees.

A two-story house with a brick exterior, a covered porch, and a stone pathway leading to the entrance.

19. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities

Riverwoods

9.8 out of 10, Exceptional, (89 reviews)

9.8/10

Exceptional

(89 reviews)

"Great spot, safe, clean, and beautiful environment would highly recommend!"

Chris F.

The price is AU$293

AU$293

includes taxes & fees

3 Nov - 4 Nov

Master qtr close to nature & easy urban facilities

A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

An outdoor deck with a brick fireplace and a grill.

A living room with a brick fireplace, a black leather sofa, a round ottoman, and a flat-screen TV mounted on the wall.

A two-story house with a stone facade, a front porch, and a black front door.

20. 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

9.6 out of 10, Exceptional, (25 reviews)

9.6/10

Exceptional

(25 reviews)

"Great place Great location "

Josh W.

The price is AU$586

AU$586

includes taxes & fees

2 Nov - 3 Nov

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

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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Chicago Holiday Homes information

Number of reviews	301
Accommodation	771 Holiday Homes
Lowest Price	AU$293
Highest Price	AU$2,545

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Chicago Holiday Rentals

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Holiday Homes in Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chicago holiday homes

1. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

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

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

4. Chicago Riverhouse with private fenced in oasis

5. Vibrant House, Walk to Train, Game Room

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

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

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

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

10. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

11. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

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

13. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

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

15. LUXE 3 BR, 2 BA + Hot Tub

16. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

17. 3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

18. Premier 9BR Art Deco manor with garage.

19. Master qtr close to nature & easy urban facilities

20. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Find holiday rentals that suit your style

Top Chicago Hotel Reviews

L7 Chicago by LOTTE

Find out more about Chicago

Chicago Holiday Homes information

Explore a world of travel with Expedia