Chicago Holiday Houses | Expedia.co.nz

Chicago Holiday Homes
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Holiday Homes
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Our top choices for Chicago holiday homes

A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

A bedroom with a large bed, a window, and three framed documents on the wall.

A modern office space with a large meeting table, comfortable seating, and large windows offering a view of the city.

1. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments

Near North Side

9.6 out of 10, Exceptional, (25 reviews)

9.6/10

Exceptional

(25 reviews)

"Beautiful place and location! Had a great time with my family here"

Pedro C.

The price is NZ$1,714

NZ$1,714

includes taxes & fees

16 Sept - 17 Sept

ENVITAE Hotel, 4BR Luxury Modern Apartments

A spacious living room with a large sectional sofa, a glass coffee table, and a wooden staircase.

A pub with outdoor seating, a brick facade, and a sign indicating it was established in 1972.

A bedroom with a bed, a desk, a chair, a wardrobe, and a ceiling fan.

A dining area with a glass table, four chairs, and a view of the kitchen through a doorway.

2. Scott C.H. - Chicago Getaway

Scott C.H. - Chicago Getaway

Near North Side

The price is NZ$2,086

NZ$2,086

includes taxes & fees

10 Sept - 11 Sept

Scott C.H. - Chicago Getaway

A living room with a sectional sofa, a round wooden coffee table, and three framed artworks on the wall.

A wooden deck with a wicker chair and a table, a potted plant, and a house in the background.

A gym with cardio equipment, weight benches, and a treadmill.

A room with a foosball table, a dartboard, and arcade machines.

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)

10/10

Exceptional

(4 reviews)

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

Jason

The price is NZ$908

NZ$908

includes taxes & fees

30 Aug - 31 Aug

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

A modern interior with large windows, a wooden floor, and a conference table with chairs.

A modern living room with a sofa, a round coffee table, a plant, and a view of the city through large windows.

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)

9.6/10

Exceptional

(4 reviews)

"Really enjoyed staying at this property! Clean and safe. Would recommend!"

Emmeline R.

The price is NZ$2,122

NZ$2,122

includes taxes & fees

18 Sept - 19 Sept

Modern 3BR Apartment Near North Ave Shops

A dining room with a large table, four chairs, a vase, and a mirror on the wall.

A home theater room with black leather recliners, a popcorn machine, and a wall of movie posters.

A staircase with patterned carpeted steps and black balusters, leading to a landing with a framed picture on the wall.

A four-poster bed in a room with a window and a framed picture on the wall.

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!

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

Arcade • Theater • Gym • Office • Sleeps 15

Portage Park

8.8 out of 10, Excellent, (3 reviews)

8.8/10

Excellent

(3 reviews)

"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."

Latasha C.

The price is NZ$1,169

NZ$1,169

includes taxes & fees

31 Aug - 1 Sept

Arcade • Theater • Gym • Office • Sleeps 15

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

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

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

A wicker outdoor seating area with a table set for a meal, including fruits and wine glasses.

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)

9.4/10

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."

kim r.

The price is NZ$744

NZ$744

includes taxes & fees

31 Aug - 1 Sept

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

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

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

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

A bedroom with a bed, a nightstand, a lamp, and a door.

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)

10/10

Exceptional

(3 reviews)

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

Willow M.

The price is NZ$538

NZ$538

includes taxes & fees

1 Sept - 2 Sept

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

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

A room with a desk, a chair, a TV mounted on the wall displaying various streaming services, a window with a blind, and a framed picture on the wall.

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

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

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)

9.8/10

Exceptional

(86 reviews)

"Lovely, quiet property with easy access to retail & restaurants. Perfect for a long weekend away."

Suzanne H.

The price is NZ$342

NZ$342

includes taxes & fees

7 Sept - 8 Sept

Master qtr close to nature & easy urban facilities

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

A single-story house with a front porch, a staircase leading to the entrance, and a driveway.

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.

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)

7.8/10

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."

Amal

The price is NZ$506

NZ$506

includes taxes & fees

31 Aug - 1 Sept

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

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 potted plant, a flat-screen TV, a dining table with chairs, and a clock on the wall.

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.

11. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

8.6 out of 10, Excellent, (54 reviews)

8.6/10

Excellent

(54 reviews)

"Hot tub was very nice!"

Jeff

The price is NZ$620

NZ$620

includes taxes & fees

2 Sept - 3 Sept

LUXE 3 BR, 2 BA + Hot Tub

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 bedroom with a bed, a dresser, a TV on the wall, and a door leading to a bathroom.

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)

10/10

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!"

Ashley Y.

The price is NZ$1,380

NZ$1,380

includes taxes & fees

8 Sept - 9 Sept

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

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

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

An outdoor deck with a brick fireplace and a grill.

A bedroom with a checkered bedspread, a tufted headboard, and a door with a white frame.

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)

9.4/10

Exceptional

(23 reviews)

"Great location and the place was immaculate. Host was very nice."

Carl M.

The price is NZ$702

NZ$702

includes taxes & fees

31 Aug - 1 Sept

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

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

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

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

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

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

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

Westmont

The price is NZ$498

NZ$498

includes taxes & fees

31 Aug - 1 Sept

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

A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

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

A bedroom with a bed, dresser, mirror, and window.

A two-story house with a white exterior and black trim, a large front window, and a small front porch.

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)

9.8/10

Exceptional

(21 reviews)

"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."

Richie S.

The price is NZ$570

NZ$570

includes taxes & fees

8 Sept - 9 Sept

Cozy Home by O'Hare + EV Plug

A white two-story house with a porch, steps, and a small table with chairs.

A stainless steel refrigerator with a built-in ice maker, a microwave, and a small oven.

A neatly made bed with white bedding and a black decorative pillow, a bedside table with a glass lamp, and a framed picture of a landscape on the wall.

A modern living room with a sofa, coffee table, and a dining area with a bowl, wine glass, and coffee cup.

16. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio

Oak Park

10.0 out of 10, Exceptional, (33 reviews)

10/10

Exceptional

(33 reviews)

"Would stay there again"

Margaret L.

The price is NZ$951

NZ$951

includes taxes & fees

1 Sept - 2 Sept

Oak Park Victorian by FLW Studio

A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

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

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

A modern kitchen with white cabinets, a stainless steel dishwasher, and a wooden countertop.

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)

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 NZ$756

NZ$756

includes taxes & fees

7 Sept - 8 Sept

Classic Forest Park Foursquare < 1 Mi to Blue Line

A modern living room with a sectional sofa, a coffee table, and a TV.

A bedroom with a bed, a chair, a table, and a window.

A modern kitchen with grey cabinets, a black refrigerator, a microwave, a stove, and a dining area with a table and chairs.

A compact kitchen with a dining table, chairs, a refrigerator, microwave, and built-in oven.

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)

8.0/10

Very good

(3 reviews)

"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"

kerston b.

The price is NZ$390

NZ$390

includes taxes & fees

30 Aug - 31 Aug

Attractive Coach House Apartment for rent in Oak Park.

A building with a sign reading "Hale Street Cantina" and a brick facade.

A white house with a garden featuring purple flowers and a birdbath.

A kitchen with white cabinets, a stainless steel refrigerator, a gas stove, a window with a view, and a rug on the floor.

A white door with a mirror above it, a white wall, and a hanging light fixture.

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

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton

10.0 out of 10, Exceptional, (70 reviews)

10/10

Exceptional

(70 reviews)

"This was the perfect place for our short stay!"

Laurie R.

The price is NZ$529

NZ$529

includes taxes & fees

6 Sept - 7 Sept

✽ Charming Cottage ✽ close to College/Town/Station

A circular fire pit with chairs around it, string lights overhead, and a house in the background.

A modern living room with a sofa, coffee table, TV, and a staircase.

A modern kitchen with white cabinets, stainless steel appliances, and a black pendant light.

A neatly arranged bedroom with a large bed, two bedside tables, and a nightstand. There are curtains on the windows, and a towel is placed on the bed.

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

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

Austin

6.0 out of 10, (1 review)

6.0/10

(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."

Adrian Cesar C.

The price is NZ$1,517

NZ$1,517

includes taxes & fees

30 Aug - 31 Aug

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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Find out more about Chicago

Chicago Holiday Homes information

Number of reviews	338
Accommodation	786 Holiday Homes
Lowest Price	NZ$342
Highest Price	NZ$2,122

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Chicago on Expedia.com

Holiday Homes in Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chicago holiday homes

1. ENVITAE Hotel, 4BR Luxury Modern Apartments

2. Scott C.H. - Chicago Getaway

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

4. Modern 3BR Apartment Near North Ave Shops

5. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

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

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

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

9. Master qtr close to nature & easy urban facilities

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

11. LUXE 3 BR, 2 BA + Hot Tub

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

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

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

15. Cozy Home by O'Hare + EV Plug

16. Oak Park Victorian by FLW Studio

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

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

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

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

Find holiday rentals that suit your style

Top Chicago Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

Find out more about Chicago

Chicago Holiday Homes information

Explore a world of travel with Expedia