West Side Holiday Houses

West Side Holiday Homes
United States of America
Holiday Homes
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A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

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Our top choices for West Side holiday homes

A cozy outdoor seating area with Adirondack chairs around a fire pit, string lights overhead, and a house in the background.

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.

A movie theater with a large screen displaying 'UNIVERSAL,' leather recliner seating, popcorn buckets, and a popcorn machine.

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

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

Firepit • Game Room • Theater • Gym • Sleeps 18

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$1,698

NZ$1,698

includes taxes & fees

29 Oct - 30 Oct

Firepit • Game Room • Theater • Gym • Sleeps 18

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

A modern living room with a grey sectional sofa, a dining table with chairs, a kitchen area, and a desk with a chair.

A laundry room with two front-loading washers, a shelf with a plant, and a wall-mounted basket.

A two-story residential building with a brick facade, large windows, and a small front porch.

2. Quiet Area - Revamped Basement

Quiet Area - Revamped Basement

Belmont Cragin

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Excellent apartment very clean and comfortable. "

Albert

The price is NZ$754

NZ$754

includes taxes & fees

29 Oct - 30 Oct

Quiet Area - Revamped Basement

A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

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.

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

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)

10/10

Exceptional

(10 reviews)

"Wonderful night, boys loved the arcade area."

Anonymous traveller

The price is NZ$1,567

NZ$1,567

includes taxes & fees

27 Oct - 28 Oct

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

4. 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 NZ$1,011

NZ$1,011

includes taxes & fees

2 Nov - 3 Nov

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

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 kitchen with a built-in counter, pendant lights, and decorative wall art.

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

5. 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 NZ$1,153

NZ$1,153

includes taxes & fees

27 Oct - 28 Oct

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

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

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

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

A modern bedroom with a large bed, a ceiling fan, a wooden wardrobe, a round mirror, and a potted plant.

6. 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 NZ$1,057

NZ$1,057

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

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.

7. 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 NZ$1,229

NZ$1,229

includes taxes & fees

9 Nov - 10 Nov

Vibrant House, Walk to Train, Game Room

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

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

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

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

Westmont

The price is NZ$495

NZ$495

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A modern kitchen with a dining area, a bar stool, and a decorative wall piece.

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

9. 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 NZ$463

NZ$463

includes taxes & fees

9 Nov - 10 Nov

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

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.

10. 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 NZ$1,371

NZ$1,371

includes taxes & fees

2 Nov - 3 Nov

Arcade • Theater • Gym • Office • Sleeps 15

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.

11. 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 NZ$359

NZ$359

includes taxes & fees

27 Oct - 28 Oct

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

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

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.

12. 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 NZ$527

NZ$527

includes taxes & fees

27 Oct - 28 Oct

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

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 grey cabinets, a white dishwasher, a stove, and a coffee maker.

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

13. 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 NZ$696

NZ$696

includes taxes & fees

18 Nov - 19 Nov

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

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

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

14. 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 NZ$583

NZ$583

includes taxes & fees

16 Nov - 17 Nov

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

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.

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

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

15. 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 NZ$683

NZ$683

includes taxes & fees

27 Oct - 28 Oct

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

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 kitchen with white cabinets, a black refrigerator, a microwave, a stove, and a window with a view.

16. 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 NZ$665

NZ$665

includes taxes & fees

27 Oct - 28 Oct

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

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

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

17. 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 NZ$629

NZ$629

includes taxes & fees

28 Oct - 29 Oct

LUXE 3 BR, 2 BA + Hot Tub

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

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

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

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

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

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

Belmont Cragin

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 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$1,005

NZ$1,005

includes taxes & fees

2 Nov - 3 Nov

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

A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

A living room with a glass coffee table, leather sofa, and a red accent wall.

A room with a bunk bed, a red rug, a white door, and a small trash can.

A spacious living area with a round dining table, multiple chairs, a sofa, and a TV.

19. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Lisle

9.4 out of 10, Exceptional, (36 reviews)

9.4/10

Exceptional

(36 reviews)

"This property was perfect for our weekend stay in the Chicagoland area. It was conveniently located to activities, shops and restaurants. Vic is a wonderfully attentive host who responds quickly and is happy to answer any questions or concerns."

Christine M.

The price is NZ$526

NZ$526

includes taxes & fees

29 Oct - 30 Oct

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

A wooden deck with a railing, a staircase, and a window with a wreath.

A dining area with a round table, chairs, a decorative vase, and a patterned rug.

A dining table with a decorative runner, candles, and a framed picture.

A two-story house with a porch, a small tree, and a sign that reads 'Ashlin House.'

20. 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, (36 reviews)

9.8/10

Exceptional

(36 reviews)

"I had a fun stay "

Jusu K.

The price is NZ$360

NZ$360

includes taxes & fees

27 Oct - 28 Oct

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

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 West Side Hotel Reviews

Hyatt Place Chicago Medical/University District

8/10 Good

"Stayed for 2 nights traveling from Ohio for a concert had never stayed in Chicago before the hotel was enough to keep us comfortable historic building with updates note. Staff was great"

Karma 2-night trip

Posted less than an hour ago

Hyatt Place Chicago Medical/University District

Hotel Chicago West Loop, SureStay Collection by Best Western

8/10 Good

"Best place to stay for walking distance to an event at the United Center. It is not the Ritz but it is serviceable, the staff is helpful, there is good local dining and parking, and it was ok for our purpose."

Richard 2-night trip

Posted 2 hours ago

Hotel Chicago West Loop, SureStay Collection by Best Western