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Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chicago vacation homes

Exterior

1. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
The price is CA $611
CA $1,210 total
includes taxes & fees
Sep 28 - Sep 29
Envitae Hotel, 4BR Modern Sleek Apartment
Game room

2. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is CA $694
CA $1,473 total
includes taxes & fees
Oct 8 - Oct 9
Wabash 4BR - Pool, Free In & Out Parking 1
Fitness facility

3. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is CA $2,768
CA $5,935 total
includes taxes & fees
Oct 13 - Oct 14
Brand New 12 Bedroom Mansion
Game room

4. 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 $106
CA $765 total
includes taxes & fees
Sep 21 - Sep 22
Theater • Game Room • Gym • Firepit • 4BR Home
Exterior

5. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
The price is CA $193
CA $414 total
includes taxes & fees
Oct 12 - Oct 13
A quiet stay while you are away
Dining

6. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (8 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 $190
CA $1,281 total
includes taxes & fees
Sep 22 - Sep 23
Sleeps 18 • 8BR • Game Room • Gym • Theater
7 bedrooms, desk, iron/ironing board, travel crib

7. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is CA $149
CA $1,037 total
includes taxes & fees
Sep 22 - Sep 23
Arcade • Theater • Gym • Office • Sleeps 15
Smart TV

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, (33 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is CA $208
CA $426 total
includes taxes & fees
Sep 22 - Sep 23
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior detail

9. 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 $162
CA $303 total
includes taxes & fees
Sep 20 - Sep 21
Master qtr close to nature & easy urban facilities
Coffee/tea maker, fridge, microwave, oven

10. 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 $176
CA $752 total
includes taxes & fees
Sep 22 - Sep 23
Game Room • Fire-pit • Playground • Gym • Billiard
Smart TV

11. 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 $160
CA $282 total
includes taxes & fees
Sep 29 - Sep 30
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Living area

12. 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 $252
CA $328 total
includes taxes & fees
Sep 22 - Sep 23
Attractive Coach House Apartment for rent in Oak Park.
Exterior

13. 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, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is CA $266
CA $485 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Dining

14. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (60 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is CA $252
CA $522 total
includes taxes & fees
Sep 22 - Sep 23
LUXE 3 BR, 2 BA + Hot Tub
Coffee/tea maker, fridge, microwave, stovetop

15. 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 $269
CA $681 total
includes taxes & fees
Sep 22 - Sep 23
Classic Forest Park Foursquare < 1 Mi to Blue Line
Terrace/patio

16. Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
The price is CA $220
CA $1,338 total
includes taxes & fees
Sep 21 - Sep 22
Sleeps 18 • 7BR • Gym • Game Room • Theater
Coffee/tea maker, fridge, microwave, oven

17. 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 $263
CA $637 total
includes taxes & fees
Sep 22 - Sep 23
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Exterior detail

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 $189
CA $498 total
includes taxes & fees
Sep 20 - Sep 21
Quaint Bungalow, near Great Lakes Naval Base
Dining

19. 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 $310
CA $727 total
includes taxes & fees
Sep 30 - Oct 1
Spacious 4BR near Northwestern with King Beds + Crib
Interior

20. 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 $221
CA $469 total
includes taxes & fees
Sep 20 - Sep 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

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"It is a bit outdated and needs an upgrade. The place is clean, well maintained however and staff helpful. The room needs more outlets. Outlets are located on the desk and very slow to fully charge phone. Location is great! Everything is in walking distance- Grant and Millennium Parks, Michigan Ave, bus/train easily accessible, State St for shopping, etc. No refrigerator nor microwave in the room."
Morenike 5-night trip
Posted less than an hour ago
Travelodge by Wyndham Downtown Chicago

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
139
Accommodation
793 Vacation Homes
Lowest Price
CA $282
Highest Price
CA $1,473

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