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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chicago vacation homes

Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

1. 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 $212
CA $932 total
includes taxes & fees
Oct 15 - Oct 16
Theater • Game Room • Gym • Firepit • 4BR Home
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

2. 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
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is CA $210
CA $349 total
includes taxes & fees
Oct 25 - Oct 26
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern living room with a sectional sofa, a coffee table, and a TV.

3. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is CA $257
CA $335 total
includes taxes & fees
Oct 13 - Oct 14
Attractive Coach House Apartment for rent in Oak Park.
Room

4. 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 $350
CA $1,309 total
includes taxes & fees
Oct 21 - Oct 22
Arcade • Theater • Gym • Office • Sleeps 15
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, (9 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is CA $336
CA $1,503 total
includes taxes & fees
Oct 22 - Oct 23
Sleeps 18 • 8BR • Game Room • Gym • Theater
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is CA $186
CA $438 total
includes taxes & fees
Nov 9 - Nov 10
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.

7. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (88 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is CA $153
CA $298 total
includes taxes & fees
Oct 19 - Oct 20
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.

8. 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)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is CA $212
CA $429 total
includes taxes & fees
Oct 12 - Oct 13
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A single-story house with a covered porch, a front door, and a small garden area.

9. 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 $293
CA $518 total
includes taxes & fees
Oct 29 - Oct 30
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

10. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (26 reviews)
"clean, good access to highway. nice neighborhood."
United States
Jay Z.
The price is CA $203
CA $458 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Home by O'Hare + EV Plug
A two-story house with a garage, solar panels, and a red car parked in front.

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

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is CA $177
CA $555 total
includes taxes & fees
Oct 12 - Oct 13
Lombard 1BR & 1BH Suite Close to freeway & Mall
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

12. 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 $257
CA $529 total
includes taxes & fees
Oct 12 - Oct 13
LUXE 3 BR, 2 BA + Hot Tub
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

13. 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 $274
CA $691 total
includes taxes & fees
Oct 14 - Oct 15
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern kitchen with a marble countertop, stainless steel appliances, and light wood flooring.

14. 3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
The price is CA $257
CA $646 total
includes taxes & fees
Oct 12 - Oct 13
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

15. 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 $642
CA $1,221 total
includes taxes & fees
Oct 12 - Oct 13
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern kitchen with white cabinets, a black stove, and a microwave.

16. Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (83 reviews)
"It was a very clean place, comfortable furniture and beds e.c.t."
United States
Ronald H.
The price is CA $278
CA $512 total
includes taxes & fees
Oct 29 - Oct 30
Your Next Vacation Home
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

17. 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 $759
CA $2,755 total
includes taxes & fees
Nov 2 - Nov 3
Premier 9BR Art Deco manor with garage.
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.

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

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is CA $349
CA $496 total
includes taxes & fees
Oct 12 - Oct 13
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A building with a sign reading 'Hale Street Cantina' and a brick facade.

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 $257
CA $464 total
includes taxes & fees
Oct 13 - Oct 14
✽ Charming Cottage ✽ close to College/Town/Station
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

20. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is CA $642
CA $1,451 total
includes taxes & fees
Oct 12 - Oct 13
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Hotel was unique and enjoyed the location. Room was very basic but functional. Lobby was very welcoming."
Lindsey Marie 3-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
595
Accommodation
744 Vacation Homes
Lowest Price
CA $298
Highest Price
CA $2,755

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