West Side, IL Vacation Homes from ￥14,054

A building with a sign reading "GARDEN BABY CONSERVATORY" and a red door.

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Our top choices for West Side vacation homes

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

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

Austin

Adrian Cesar C.

￥148,343 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Portage Park

Anonymous traveler

￥142,126 total

includes taxes & fees

Nov 17 - Nov 18

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

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

Westmont

Kelly K.

￥46,149 total

includes taxes & fees

Dec 1 - Dec 2

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

Belmont Cragin

Jason

￥86,388 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Belmont Cragin

Rhiannon

￥78,456 total

includes taxes & fees

Nov 16 - Nov 17

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

6. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

Oak Park

Willow M.

￥61,835 total

includes taxes & fees

Dec 1 - Dec 2

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

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

Maywood

Carl T.

￥46,048 total

includes taxes & fees

Nov 16 - Nov 17

A garage with a white door, brick pillars, and a car parked inside.

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

Oak Park

￥58,144 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Westmont

Tomas R.

￥41,132 total

includes taxes & fees

Nov 22 - Nov 23

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

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

Brookfield

Steve H.

￥69,575 total

includes taxes & fees

Nov 15 - Nov 16

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

11. LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

Brenda M

￥56,213 total

includes taxes & fees

Nov 18 - Nov 19

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

12. Master qtr close to nature & easy urban facilities

Riverwoods

Chris F.

￥33,192 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Robertsdale

Scott n Holly K.

￥31,502 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Lincoln Park

Jill L.

￥89,080 total

includes taxes & fees

Nov 15 - Nov 16

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.

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

Highland Hills

"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.

￥65,317 total

includes taxes & fees

Nov 18 - Nov 19

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

16. Oak Park Victorian by FLW Studio

Oak Park

Margaret L.

￥87,031 total

includes taxes & fees

Nov 18 - Nov 19

A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

17. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

Near South Side

"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"

Ilir T.

￥77,512 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Forest Park

LEM R.

￥73,639 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

19. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Hazel Green

Nick L.

￥53,479 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Westchester

"We had a great time at this property while our family explored Chicago. We found everything about the property was awesome for our family. Sitting outside with coffee in the morning was fantastic. Quiet neighborhood and very close to grocery store. We would stay there again. If we had to make any recommendations it would be that the living room could use more seating as we were five adults and had to use kitchen chairs for all to have a seat. I would also consider new sofa downstairs. It sits...

Stephen K.

￥70,388 total

includes taxes & fees

Nov 15 - Nov 16

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Discover things to see and do in West Side as you venture to popular sights like United Center.

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Top reviews in West Side

A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

The Publishing House B&B

Downtown Chicago

10/10 Excellent

Vanessa

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A modern indoor pool area with lounge chairs, a wooden table, and large windows.

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

10/10 Excellent

Rashad

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

Hotel Riu Plaza Chicago

Downtown Chicago

10/10 Excellent

We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...

Donna

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

10/10 Excellent

Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.

Michael

A hotel lobby with a bar area, a chandelier, and a reception desk.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Excellent

Sergio

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Griffin

A modern lounge area with a fire feature, seating, and a bar.

Hyatt Place Chicago/Wicker Park

West Town

10/10 Excellent

Shelby

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

10/10 Excellent

We will definitely be staying here again! Great location, clean room, and great service. They even have a great complimentary breakfast which is a must have in a city like Chicago. The staff was great also. We had to switch trains for an earlier one due to weather and got into Chicago in the AM. Check in is 4pm and with two small children we were worried about what to do for hours but the staff helped us out and luckily had a room available.

Alexander

Arlo Chicago

Downtown Chicago

10/10 Excellent

Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel...

Lina