Northwest Side Holiday Houses

Northwest Side Holiday Homes
United States of America
Holiday Homes
Expedia.co.nz

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A curved pathway with a metal fence, flowering trees, and a street lamp.

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Our top choices for Northwest Side holiday homes

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

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

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

A bedroom with a large bed, two bedside tables, a window with curtains, and a wooden floor.

1. 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

1 Sept - 2 Sept

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

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

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

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

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

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

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

4. 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.

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

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 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.

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

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

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

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

6. 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

1 Sept - 2 Sept

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

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.

7. 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 stainless steel appliances, wooden cabinets, and a tiled backsplash.

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

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

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

8. 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$690

NZ$690

includes taxes & fees

1 Sept - 2 Sept

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

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

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

9. 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$807

NZ$807

includes taxes & fees

8 Sept - 9 Sept

Classic Forest Park Foursquare < 1 Mi to Blue Line

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

A modern kitchen with white cabinets, a built-in microwave, a coffee maker, and a sink.

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

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

10. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

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

Lincoln Park

The price is NZ$1,098

NZ$1,098

includes taxes & fees

31 Aug - 1 Sept

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

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 bathroom with a bathtub, toilet, and sink.

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

11. 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 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 modern kitchen with dark wooden cabinets, a white stove, a microwave, and a sink.

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

12. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

8.6 out of 10, Excellent, (55 reviews)

8.6/10

Excellent

(55 reviews)

"Hot tub was very nice!"

Jeff

The price is NZ$620

NZ$620

includes taxes & fees

10 Sept - 11 Sept

LUXE 3 BR, 2 BA + Hot Tub

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

A living room with a black sofa, two white armchairs, a wooden coffee table, and a patterned rug.

13. 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$584

NZ$584

includes taxes & fees

20 Sept - 21 Sept

Cozy Home by O'Hare + EV Plug

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

A round black coffee table with a wooden board holding grapes, cheese, and crackers. A bottle of wine and a book titled "Luxury Chaletlets" are on the table.

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

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

14. 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

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

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

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

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

15. 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$344

NZ$344

includes taxes & fees

7 Sept - 8 Sept

Master qtr close to nature & easy urban facilities

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

16. 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$1,713

NZ$1,713

includes taxes & fees

16 Sept - 17 Sept

ENVITAE Hotel, 4BR Luxury Modern Apartments

A spacious living room with a blue sofa, a dining area with blue chairs, a kitchen with a white countertop, and a fireplace.

A bedroom with a bed, a black sofa, a small round table, and a staircase.

A kitchen area with a countertop, stools, and a sign that reads "KITCHEN".

A spacious living area with a sofa, dining table, and chairs, a kitchen with wooden cabinets, and a large window offering a view of greenery.

17. Spacious Des Plaines Home - Near Airport, Casino & Arena

Spacious Des Plaines Home - Near Airport, Casino & Arena

Des Plaines

8.0 out of 10, Very good, (2 reviews)

8.0/10

Very good

(2 reviews)

"It was a nice area."

Sherice S.

The price is NZ$742

NZ$742

includes taxes & fees

31 Aug - 1 Sept

Spacious Des Plaines Home - Near Airport, Casino & Arena

A modern kitchen with white cabinets, a black stove, and a microwave.

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

A modern entryway with a grey wall, a white door, and a view of a green field through a large window.

A modern living room with a gray sofa, a dining table with chairs, a ceiling fan, and a TV mounted on the wall.

18. Your Next Vacation Home

Your Next Vacation Home

Oakton

9.4 out of 10, Exceptional, (81 reviews)

9.4/10

Exceptional

(81 reviews)

"Peaceful and quiet with a great lake to fish and pedal boat on. Clean and a great space for kids!"

Ashley L.

The price is NZ$591

NZ$591

includes taxes & fees

1 Sept - 2 Sept

Your Next Vacation Home

A modern living room with a sofa, coffee table, TV, and a staircase leading to an upper floor.

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden shelf with dishes.

A bedroom with a bed, a rocking chair, a nightstand, and a window.

A dining table with a potted plant, a checkered tray, and a staircase in the background.

19. Spacious 5BR 2BA Berwyn Home

Spacious 5BR 2BA Berwyn Home

Berwyn

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

The price is NZ$975

NZ$975

includes taxes & fees

30 Aug - 31 Aug

Spacious 5BR 2BA Berwyn Home

A dining area with a marble table, a potted plant, and a checkered coaster.

A kitchen with white cabinets, a clock, a coffee maker, and a dishwasher.

A living room with a TV, sofa, coffee table, and artwork on the walls.

A dining area with a table and chairs, a staircase, and a framed picture on the wall.

20. Spacious 5-bed 2-bath house - Berwyn

Spacious 5-bed 2-bath house - Berwyn

Berwyn

The price is NZ$942

NZ$942

includes taxes & fees

8 Sept - 9 Sept

Spacious 5-bed 2-bath house - Berwyn

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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