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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 $99
CA $775 total
includes taxes & fees
Oct 5 - Oct 6
Theater • Game Room • Gym • Firepit • 4BR Home
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

2. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (31 reviews)
"Super clean great location short drive to everything we wanted to see!"
United States
eric p.
The price is CA $291
CA $765 total
includes taxes & fees
Oct 14 - Oct 15
ENVITAE Hotel, 4BR Luxury Modern Apartments
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

3. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

4. 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 $306
CA $1,461 total
includes taxes & fees
Oct 5 - Oct 6
Sleeps 18 • 8BR • Game Room • Gym • Theater
A modern kitchen with wooden cabinets, stainless steel appliances, and a white tiled backsplash.

5. 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)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
The price is CA $580
CA $1,320 total
includes taxes & fees
Oct 8 - Oct 9
Wabash 4BR - Pool, Free In & Out Parking 1
Room

6. 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 $248
CA $1,161 total
includes taxes & fees
Oct 4 - Oct 5
Arcade • Theater • Gym • Office • Sleeps 15
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 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 $219
CA $812 total
includes taxes & fees
Oct 6 - Oct 7
Game Room • Fire-pit • Playground • Gym • Billiard
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

8. 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, (44 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 $443
CA $946 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern living room with a sectional sofa, a coffee table, and a TV.

9. 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 $331 total
includes taxes & fees
Oct 4 - Oct 5
Attractive Coach House Apartment for rent in Oak Park.
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

10. 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 $434 total
includes taxes & fees
Oct 12 - Oct 13
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is CA $178
CA $429 total
includes taxes & fees
Oct 4 - Oct 5
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.

12. 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 $276
CA $500 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

13. 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 $430
CA $1,005 total
includes taxes & fees
Oct 8 - Oct 9
Chicago Riverhouse with private fenced in oasis
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

14. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (63 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is CA $256
CA $526 total
includes taxes & fees
Oct 14 - Oct 15
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.

15. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (87 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is CA $165
CA $310 total
includes taxes & fees
Oct 8 - Oct 9
Master qtr close to nature & easy urban facilities
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

16. 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 $182
CA $311 total
includes taxes & fees
Oct 26 - Oct 27
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A two-story house with a garage, solar panels, and a red car parked in front.

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

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is CA $177
CA $550 total
includes taxes & fees
Oct 13 - Oct 14
Lombard 1BR & 1BH Suite Close to freeway & Mall
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

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 $689 total
includes taxes & fees
Oct 14 - Oct 15
Classic Forest Park Foursquare < 1 Mi to Blue Line
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

19. 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 $513
CA $1,277 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

20. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (24 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is CA $212
CA $468 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Home by O'Hare + EV Plug
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 Godfrey Hotel Chicago

The Godfrey Hotel Chicago

10/10 Excellent
"Great hotel - great rooms - nice restaurant and bar"
Carrie 1-night trip
Posted 4 hours ago
The Godfrey Hotel Chicago

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
360
Accommodation
744 Vacation Homes
Lowest Price
CA $310
Highest Price
CA $1,461

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