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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

A living room with a flat-screen TV mounted on the wall, a plant on a stand, 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
The price is CA $343
CA $1,157 total
includes taxes & fees
Oct 6 - Oct 7
4 BR • Theater Room • Gym • Walk to Lincoln Park!
Room

2. 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 $148
CA $1,033 total
includes taxes & fees
Oct 1 - Oct 2
Arcade • Theater • Gym • Office • Sleeps 15
Lounge by the fire pit

3. 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 $129
CA $814 total
includes taxes & fees
Oct 5 - Oct 6
Theater • Game Room • Gym • Firepit • 4BR Home
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

4. 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 $169
CA $314 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.

5. 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)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is CA $211
CA $431 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.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is CA $158
CA $404 total
includes taxes & fees
Oct 1 - Oct 2
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

7. 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 $255
CA $523 total
includes taxes & fees
Oct 6 - Oct 7
LUXE 3 BR, 2 BA + Hot Tub
A single-story house with a covered porch, a front door, and a small garden area.

8. 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 $269
CA $490 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern kitchen with wooden cabinets, stainless steel appliances, and a white tiled backsplash.

9. 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 $570
CA $1,303 total
includes taxes & fees
Oct 8 - Oct 9
Wabash 4BR - Pool, Free In & Out Parking 1
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

10. Spacious 4BR near Northwestern with King Beds + Crib

Spacious 4BR near Northwestern with King Beds + Crib
Evanston
10.0 out of 10, Exceptional, (5 reviews)
"Spacious home that accommodates all our guests. Very close to Northwestern University so travel was easy! Home was clean and well taken care of. Would definitely recommend to others and would stay agin when I’m in the area."
United States
Melissa C.
Spacious 4BR near Northwestern with King Beds + Crib
A modern living room with a sectional sofa, a coffee table, and a TV.

11. 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 $255
CA $329 total
includes taxes & fees
Oct 4 - Oct 5
Attractive Coach House Apartment for rent in Oak Park.
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

12. 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 $272
CA $688 total
includes taxes & fees
Oct 1 - Oct 2
Classic Forest Park Foursquare < 1 Mi to Blue Line
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

13. 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 $154
CA $720 total
includes taxes & fees
Oct 1 - Oct 2
Game Room • Fire-pit • Playground • Gym • Billiard
A white two-story house with a porch, steps, and a small table with chairs.

14. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is CA $331
CA $838 total
includes taxes & fees
Oct 6 - Oct 7
Oak Park Victorian by FLW Studio
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

15. 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 $201
CA $455 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Home by O'Hare + EV Plug
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

16. 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 $201
CA $1,311 total
includes taxes & fees
Oct 5 - Oct 6
Sleeps 18 • 8BR • Game Room • Gym • Theater
A two-story house with a stone chimney, a front porch with steps, and a flag.

17. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (75 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is CA $191
CA $506 total
includes taxes & fees
Oct 25 - Oct 26
Quaint Bungalow, near Great Lakes Naval Base
A building with a sign reading 'Hale Street Cantina' and a brick facade.

18. ✽ 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 $255
CA $457 total
includes taxes & fees
Oct 8 - Oct 9
✽ Charming Cottage ✽ close to College/Town/Station
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

19. 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 $179
CA $306 total
includes taxes & fees
Oct 26 - Oct 27
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern kitchen with stainless steel appliances, grey cabinetry, and pendant lighting.

20. AeroStay Retreat – 4BR Home Near O’Hare Airport!

AeroStay Retreat – 4BR Home Near O’Hare Airport!
Wood Dale
9.4 out of 10, Exceptional, (3 reviews)
"Large space great for family"
United States
Remona S.
The price is CA $333
CA $735 total
includes taxes & fees
Oct 6 - Oct 7
AeroStay Retreat – 4BR Home Near O’Hare Airport!
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

Hilton Chicago

Hilton Chicago

8/10 Good
"It was my first time in Chicago. Stay was ok. But breakfast was not included."
Monica 3-night trip
Posted 6 hours ago
Hilton Chicago

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
206
Accommodation
794 Vacation Homes
Lowest Price
CA $306
Highest Price
CA $1,311

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