Chicago Vacation Home Rentals from CA $291: Search Top Private Vacation Homes for Rent

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Our top choices for Chicago vacation homes

A modern lounge area with a large window, a sofa, ottomans, and a coffee table.

A modern bedroom with a large bed, a window with blinds, a bedside table, and a floor lamp.

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

A modern conference room with a long table, multiple chairs, and pendant lighting.

1. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1

Downtown Chicago

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Property is new and really nice. Super clean and well put together. Would stay here again."

Devin D.

The price is CA $220

CA $220

CA $804 total

includes taxes & fees

Oct 26 - Oct 27

Wabash 4BR - Pool, Free In & Out Parking 1

A kitchen with a white countertop, dark wooden stools, and a window with decorative iron bars.

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

A modern living room with a dark wood floor, a black sofa, a black entertainment unit with a gold lamp, and a black and white decor piece on the wall.

A modern living room with a flat-screen TV mounted above a fireplace, flanked by two large potted plants.

2. 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 CA $267

CA $267

CA $1,064 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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

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.

3. 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 CA $147

CA $147

CA $708 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

4. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments

Near North Side

9.2 out of 10, Wonderful, (34 reviews)

9.2/10

Wonderful

(34 reviews)

"Super clean great location short drive to everything we wanted to see!"

eric p.

The price is CA $279

CA $279

CA $741 total

includes taxes & fees

Oct 25 - Oct 26

ENVITAE Hotel, 4BR Luxury Modern Apartments

A bedroom with a bed, bedside table, lamp, dresser, chair, and two windows with blinds.

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.

A room with a desk, chair, computer, lamp, and potted plants.

5. 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 CA $238

CA $238

CA $540 total

includes taxes & fees

Oct 28 - Oct 29

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

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 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.

6. 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 CA $193

CA $193

CA $1,268 total

includes taxes & fees

Oct 25 - Oct 26

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

✔️ 2-Way Coffee maker (K-Cup Pods or Grounds) ✔️ K-Cup pods (upon request and availability)

✔️ Toaster, blender, mixer, Crockpot, ice maker, electric water heater

7. 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 CA $170

CA $170

CA $862 total

includes taxes & fees

Nov 2 - Nov 3

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

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 gray sofa, and a patterned rug.

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.

8. 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 CA $252

CA $252

CA $523 total

includes taxes & fees

Oct 26 - Oct 27

LUXE 3 BR, 2 BA + Hot Tub

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

A modern living room with a sofa, coffee table, and large windows.

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

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

9. 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 CA $300

CA $300

CA $824 total

includes taxes & fees

Nov 1 - Nov 2

Chicago Riverhouse with private fenced in oasis

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

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

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

A kitchen with a coffee maker, a stove, and a window.

10. 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 CA $261

CA $261

CA $480 total

includes taxes & fees

Nov 16 - Nov 17

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

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

A spacious living area with a sofa, a dining table, and a kitchen in the background.

A covered outdoor area with wooden flooring, a green bench, a small table, and a potted plant.

A bed with a white headboard, a bedside lamp, and a small table with a vase of flowers.

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

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

Lincoln Park

9.6 out of 10, Exceptional, (45 reviews)

9.6/10

Exceptional

(45 reviews)

"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."

Alison G.

The price is CA $480

CA $480

CA $989 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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, (34 reviews)

7.8/10

Good

(34 reviews)

"Very nice home with basement bar. Host was very accommodating."

Carl T.

The price is CA $208

CA $208

CA $425 total

includes taxes & fees

Oct 26 - Oct 27

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

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.

13. 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 CA $238

CA $238

CA $381 total

includes taxes & fees

Nov 24 - Nov 25

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

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

A covered outdoor deck with a table and chairs, surrounded by a white railing.

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.

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

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

Westmont

The price is CA $165

CA $165

CA $412 total

includes taxes & fees

Oct 26 - Oct 27

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

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 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.

15. 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 CA $150

CA $150

CA $291 total

includes taxes & fees

Oct 27 - Oct 28

Master qtr close to nature & easy urban facilities

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

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

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.

16. 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 CA $269

CA $269

CA $682 total

includes taxes & fees

Nov 1 - Nov 2

Classic Forest Park Foursquare < 1 Mi to Blue Line

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.

An open door leading to a dining area with a table and chairs, a rug, and a hanging light fixture.

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.

17. 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 CA $315

CA $315

CA $816 total

includes taxes & fees

Nov 2 - Nov 3

Oak Park Victorian by FLW Studio

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

A dining area with a white table, two white chairs, and a vase of orange flowers.

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.

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

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton

10.0 out of 10, Exceptional, (74 reviews)

10/10

Exceptional

(74 reviews)

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

Laurie R.

The price is CA $252

CA $252

CA $456 total

includes taxes & fees

Nov 15 - Nov 16

✽ Charming Cottage ✽ close to College/Town/Station

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

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

19. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug

Des Plaines

9.8 out of 10, Exceptional, (26 reviews)

9.8/10

Exceptional

(26 reviews)

"We enjoyed our 2 night stay. The home was exactly what we were expecting. It is on a quiet street and is within walking distance to several restaurants. The beds were comfortable and and the lower level bathroom was especially nice to get ready in."

KIM K.

The price is CA $210

CA $210

CA $463 total

includes taxes & fees

Nov 2 - Nov 3

Cozy Home by O'Hare + EV Plug

A single-story brick house with a front door, a garage door, and a small front yard with a hedge and a lawn.

A modern bathroom with a large sink, toilet, and bathtub.

A well-maintained lawn with a house and a paved walkway.

A single-story house with a front door, a small window, and a trash can.

20. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard

The price is CA $174

CA $174

CA $546 total

includes taxes & fees

Oct 28 - Oct 29

Lombard 1BR & 1BH Suite Close to freeway & Mall

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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Chicago Vacation Homes information

Number of reviews	432
Accommodation	744 Vacation Homes
Lowest Price	CA $291
Highest Price	CA $1,268

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chicago vacation homes

1. Wabash 4BR - Pool, Free In & Out Parking 1

2. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

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

4. ENVITAE Hotel, 4BR Luxury Modern Apartments

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

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

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

8. LUXE 3 BR, 2 BA + Hot Tub

9. Chicago Riverhouse with private fenced in oasis

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

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

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

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

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

15. Master qtr close to nature & easy urban facilities

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

17. Oak Park Victorian by FLW Studio

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

19. Cozy Home by O'Hare + EV Plug

20. Lombard 1BR & 1BH Suite Close to freeway & Mall

Find vacation rentals that suit your style

Top Chicago Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Find out more about Chicago

Chicago Vacation Homes information

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