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

Search Vacation Homes in West Side

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find vacation rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

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.

￥140,062 total

includes taxes & fees

Nov 9 - Nov 10

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

￥133,931 total

includes taxes & fees

Nov 9 - Nov 10

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

3. Chicago Riverhouse with private fenced in oasis

North Park

Robert S.

￥91,007 total

includes taxes & fees

Nov 19 - Nov 20

A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

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

Oak Park

￥57,515 total

includes taxes & fees

Nov 12 - Nov 13

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

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

Belmont Cragin

Rhiannon

￥73,868 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Belmont Cragin

Jason

￥96,800 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Westmont

Kelly K.

￥45,322 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.

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

Maywood

Carl T.

￥45,407 total

includes taxes & fees

Nov 17 - Nov 18

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

9. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

Lincoln Park

Sara C.

￥107,907 total

includes taxes & fees

Nov 10 - Nov 11

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.

￥66,081 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Westmont

Tomas R.

￥38,890 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Oak Park

Willow M.

￥65,415 total

includes taxes & fees

Nov 10 - Nov 11

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

13. LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

Anonymous traveler

￥53,241 total

includes taxes & fees

Nov 9 - Nov 10

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.

￥90,370 total

includes taxes & fees

Nov 16 - Nov 17

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

15. Master qtr close to nature & easy urban facilities

Riverwoods

Chris F.

￥31,229 total

includes taxes & fees

Nov 10 - Nov 11

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.

16. 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.

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.

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

Hazel Green

Nick L.

￥50,713 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Robertsdale

Jusu K.

￥29,829 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Forest Park

LEM R.

￥69,415 total

includes taxes & fees

Nov 9 - Nov 10

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

20. Oak Park Victorian by FLW Studio

Oak Park

Margaret L.

￥93,353 total

includes taxes & fees

Nov 10 - Nov 11

View all properties

Learn more about West Side

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

See all hotels in West Side

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 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 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 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

A rooftop terrace with outdoor seating, a fire feature, and a modern building with large windows.

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

A grand hotel facade with classical architecture, featuring tall columns, ornate detailing, and a prominent entrance with a marquee.

Hyatt House Chicago Medical/University District

Near West Side

10/10 Excellent

Fuller

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Downtown Chicago

10/10 Excellent

Lyn

A cozy room with a sofa, a dining table, and a window with a view of buildings.

LIVN - West Loop Chicago

Downtown Chicago

10/10 Excellent

Merri

A modern lobby with a sofa, coffee table, and potted plants.

The Emily Hotel

Downtown Chicago

10/10 Excellent

Marvene

A breakfast setting with a plate of toast, a bowl of fruit, a cup of coffee, and a newspaper on a table by a window with a city view.

The Robey, Chicago, a Member of Design Hotels

West Town

10/10 Excellent

Kathleen

Hyatt Place Chicago Medical/University District

Near West Side

10/10 Excellent

Vanity

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

10/10 Excellent

The staff was amazing and the room was super spacious and clean!! The best layout of a room for a family of 3 who enjoy separate beds and a little privacy. We had the room with two queen beds and a sofa. Amazing view of chicago from the sky deck and the pool was a nice temp! Breakfast had great options and was delicious! Rosemary seasoned potatoes and captain crunch caught my eye! The elevator was a bit hard to navigate at times as you need a key. But great safety feature so no complaints!...

Valia

A multi-story hotel with a prominent sign reading "Crowne Plaza."

Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

10/10 Excellent

Priya

A modern hotel room with a large flat-screen TV, a desk with a chair, a bedside table, and a walk-in closet.

Courtyard by Marriott Chicago at Medical District/UIC

Near West Side

10/10 Excellent

We arrived a little early at 9am to valet the car and explore the city. We were DELIGHTED when the manager not only checked us in 6 hours early but also upgraded our single king to a double bed room with both a KING and QUEEN. We have loved the stay so far. Abby the night desk lady went above and beyond to find us drinks when the little store ran out and Evangeline at the bar was the BEST! Will recommend!

Maddie

Explore a world of travel with Expedia

Chicago Vacations
Standard Link for Chicago Vacations

Search Vacation Homes in West Side

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for West Side vacation homes

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

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

3. Chicago Riverhouse with private fenced in oasis

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

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

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

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

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

9. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

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

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

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

13. LUXE 3 BR, 2 BA + Hot Tub

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

15. Master qtr close to nature & easy urban facilities

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

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

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

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

20. Oak Park Victorian by FLW Studio

Learn more about West Side

Top reviews in West Side

The Publishing House B&B

10/10 Excellent

Explore a world of travel with Expedia