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Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chicago vacation homes

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

1. 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)
"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!"
United States
Jamiee B.
The price is CA $190
CA $963 total
includes taxes & fees
Nov 1 - Nov 2
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A modern kitchen with grey cabinets, a stainless steel microwave, a black refrigerator, and a dishwasher.

2. Quiet Area - Revamped Basement

Quiet Area - Revamped Basement
Belmont Cragin
9.0 out of 10, Wonderful, (2 reviews)
"Excellent apartment very clean and comfortable. "
United States
Albert
The price is CA $157
CA $627 total
includes taxes & fees
Oct 29 - Oct 30
Quiet Area - Revamped Basement
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

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is CA $300
CA $853 total
includes taxes & fees
Nov 1 - Nov 2
Chicago Riverhouse with private fenced in oasis
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)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is CA $115
CA $782 total
includes taxes & fees
Oct 29 - Oct 30
Theater • Game Room • Gym • Firepit • 4BR Home
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is CA $213
CA $1,309 total
includes taxes & fees
Nov 2 - Nov 3
Sleeps 18 • 8BR • Game Room • Gym • Theater
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

6. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is CA $323
CA $1,005 total
includes taxes & fees
Nov 9 - Nov 10
Vibrant House, Walk to Train, Game Room
A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

7. 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 $537 total
includes taxes & fees
Oct 30 - Oct 31
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A modern living room with a white sofa, a white armchair, and a floor lamp.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 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."
United States
kim r.
The price is CA $220
CA $811 total
includes taxes & fees
Nov 3 - Nov 4
Game Room • Fire-pit • Playground • Gym • Billiard
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is CA $174
CA $423 total
includes taxes & fees
Nov 2 - Nov 3
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A single-story house with a covered porch, a front door, and a small garden area.

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)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is CA $279
CA $499 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern living room with a dining area, a sofa set, and a television mounted on the wall.

11. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is CA $217
CA $1,119 total
includes taxes & fees
Nov 2 - Nov 3
Arcade • Theater • Gym • Office • Sleeps 15
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

12. 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)
"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."
United States
Alison G.
The price is CA $431
CA $919 total
includes taxes & fees
Oct 29 - Oct 30
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

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)
"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."
United States
Chad R.
The price is CA $238
CA $382 total
includes taxes & fees
Nov 22 - Nov 23
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
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.

14. 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)
"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...
United States
Denise G.
The price is CA $139
CA $564 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Home | King Bed | 10P | Metra |Chicago Suburb
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

15. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is CA $671
CA $2,604 total
includes taxes & fees
Nov 9 - Nov 10
Premier 9BR Art Deco manor with garage.
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

16. 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)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is CA $208
CA $425 total
includes taxes & fees
Nov 3 - Nov 4
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

17. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is CA $252
CA $523 total
includes taxes & fees
Nov 3 - Nov 4
LUXE 3 BR, 2 BA + Hot Tub
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

18. 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)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is CA $150
CA $291 total
includes taxes & fees
Nov 3 - Nov 4
Master qtr close to nature & easy urban facilities
A white house with a garden featuring purple flowers and a birdbath.

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

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (74 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is CA $252
CA $456 total
includes taxes & fees
Nov 23 - Nov 24
✽ Charming Cottage ✽ close to College/Town/Station
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

20. 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)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is CA $269
CA $676 total
includes taxes & fees
Nov 1 - Nov 2
Classic Forest Park Foursquare < 1 Mi to Blue Line
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 Chicago Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Clean clean Beautiful view of the River Helpful staff loved that I could check in early with a 50$ charge"
Sherrell 1-night trip
Posted less than an hour ago
The Royal Sonesta Chicago Downtown

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
351
Accommodation
744 Vacation Homes
Lowest Price
CA $291
Highest Price
CA $2,655

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