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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 $162
CA $927 total
includes taxes & fees
Sep 30 - Oct 1
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 $1,032 total
includes taxes & fees
Sep 30 - Oct 1
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 $141
CA $830 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 $165
CA $307 total
includes taxes & fees
Sep 30 - Oct 1
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 $422 total
includes taxes & fees
Sep 30 - Oct 1
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 $168
CA $416 total
includes taxes & fees
Sep 30 - Oct 1
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 $522 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 $266
CA $479 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 $543
CA $1,265 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.
The price is CA $240
CA $635 total
includes taxes & fees
Sep 30 - Oct 1
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 $327 total
includes taxes & fees
Oct 6 - Oct 7
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 $685 total
includes taxes & fees
Oct 14 - Oct 15
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 $170
CA $741 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 $278
CA $762 total
includes taxes & fees
Sep 30 - Oct 1
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, (23 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 $218
CA $474 total
includes taxes & fees
Oct 18 - Oct 19
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 $216
CA $1,329 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 $496 total
includes taxes & fees
Sep 30 - Oct 1
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 $456 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 $178
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 $282
CA $678 total
includes taxes & fees
Sep 30 - Oct 1
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

10/10 Excellent
"It was good..."
Michael 1-night trip
Posted less than an hour ago
Hilton Chicago

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Chicago Vacation Homes information

Number of reviews
205
Accommodation
794 Vacation Homes
Lowest Price
CA $306
Highest Price
CA $1,329

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