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Chicago Vacation Rentals

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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

1. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
Cozy Studio Suite, Steps from River North & Shops
A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

2. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Near South Side
9.0 out of 10, Wonderful, (6 reviews)
"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"
United States
Ilir T.
The price is CA $157
CA $575 total
includes taxes & fees
Sep 29 - Sep 30
Spacious 3BR · Bronzeville/South Loop · Sleeps 8

3. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is CA $165
CA $863 total
includes taxes & fees
Oct 5 - Oct 6
Theater • Game Room • Gym • Firepit • 4BR Home
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

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

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is CA $156
CA $922 total
includes taxes & fees
Sep 29 - Sep 30
4 BR • Theater Room • Gym • Walk to Lincoln Park!

5. 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 $143
CA $1,032 total
includes taxes & fees
Sep 29 - Sep 30
Arcade • Theater • Gym • Office • Sleeps 15
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

6. 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 $210
CA $430 total
includes taxes & fees
Sep 29 - Sep 30
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a sectional sofa, a coffee table, and a TV.

7. 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 house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

8. 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 $164
CA $309 total
includes taxes & fees
Sep 30 - Oct 1
Master qtr close to nature & easy urban facilities
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 $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.

10. 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 $1,302 total
includes taxes & fees
Oct 8 - Oct 9
Wabash 4BR - Pool, Free In & Out Parking 1
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

11. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (62 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is CA $255
CA $527 total
includes taxes & fees
Sep 29 - Sep 30
LUXE 3 BR, 2 BA + Hot Tub
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
Sep 29 - Sep 30
Classic Forest Park Foursquare < 1 Mi to Blue Line
A white two-story house with a porch, steps, and a small table with chairs.

13. 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 $268
CA $758 total
includes taxes & fees
Sep 29 - Sep 30
Oak Park Victorian by FLW Studio
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

14. 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 $180
CA $307 total
includes taxes & fees
Oct 25 - Oct 26
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
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 $211
CA $460 total
includes taxes & fees
Oct 15 - Oct 16
Cozy Home by O'Hare + EV Plug
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

16. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.4 out of 10, Exceptional, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is CA $227
CA $596 total
includes taxes & fees
Sep 29 - Sep 30
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is CA $181
CA $432 total
includes taxes & fees
Sep 29 - Sep 30
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A two-story house with a stone chimney, a front porch with steps, and a flag.

18. 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 $501 total
includes taxes & fees
Sep 29 - Sep 30
Quaint Bungalow, near Great Lakes Naval Base
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 $255
CA $456 total
includes taxes & fees
Oct 7 - Oct 8
✽ Charming Cottage ✽ close to College/Town/Station
A two-story house with a garage, solar panels, and a red car parked in front.

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

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is CA $176
CA $550 total
includes taxes & fees
Oct 4 - Oct 5
Lombard 1BR & 1BH Suite Close to freeway & Mall
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
"Have a friendly, knowledgeable and polite staff. Hotel in an ideal location, rooms are clean, restaurant in hotel. It's in walking distance to numerous downtown amenities, sights, museums, parks, etc."
Ricky 3-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
275
Accommodation
794 Vacation Homes
Lowest Price
CA $307
Highest Price
CA $1,302

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