A river with a yellow boat, surrounded by tall buildings and a bridge.

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Check prices for these dates

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

Our top choices for Chicago holiday homes

A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

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 HK$2,667
HK$5,673 total
includes taxes & fees
28 Sept - 29 Sept
Envitae Hotel, 4BR Modern Sleek Apartment
A billiards room with multiple tables, large windows, and a high ceiling with exposed ductwork.

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

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is HK$3,891
HK$8,258 total
includes taxes & fees
8 Oct - 9 Oct
Wabash 4BR - Pool, Free In & Out Parking 1
A modern gym with various exercise equipment, including a bench press, dumbbells, and a treadmill.

3. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is HK$15,423
HK$32,962 total
includes taxes & fees
13 Oct - 14 Oct
Brand New 12 Bedroom Mansion

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 HK$641
HK$4,373 total
includes taxes & fees
21 Sept - 22 Sept
Theater • Game Room • Gym • Firepit • 4BR Home
A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

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 HK$1,056
HK$2,278 total
includes taxes & fees
16 Oct - 17 Oct
A quiet stay while you are away
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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 HK$1,074
HK$7,104 total
includes taxes & fees
22 Sept - 23 Sept
Sleeps 18 • 8BR • Game Room • Gym • Theater

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 HK$909
HK$5,829 total
includes taxes & fees
22 Sept - 23 Sept
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.

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 HK$1,165
HK$2,354 total
includes taxes & fees
21 Sept - 22 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

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 HK$911
HK$1,714 total
includes taxes & fees
20 Sept - 21 Sept
Master qtr close to nature & easy urban facilities
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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 HK$1,019
HK$4,197 total
includes taxes & fees
22 Sept - 23 Sept
Game Room • Fire-pit • Playground • Gym • Billiard
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

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 HK$988
HK$1,696 total
includes taxes & fees
28 Sept - 29 Sept
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern living room with a sectional sofa, a coffee table, and a TV.

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 HK$1,412
HK$1,823 total
includes taxes & fees
22 Sept - 23 Sept
Attractive Coach House Apartment for rent in Oak Park.
A single-story house with a covered porch, a front door, and a small garden area.

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 HK$1,497
HK$2,692 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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, (58 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is HK$1,412
HK$2,912 total
includes taxes & fees
21 Sept - 22 Sept
LUXE 3 BR, 2 BA + Hot Tub
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

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 HK$1,506
HK$3,768 total
includes taxes & fees
22 Sept - 23 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
A circular fire pit with chairs around it, string lights overhead, and a house in the background.

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 HK$1,236
HK$7,442 total
includes taxes & fees
21 Sept - 22 Sept
Sleeps 18 • 7BR • Gym • Game Room • Theater
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

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 HK$1,466
HK$3,440 total
includes taxes & fees
22 Sept - 23 Sept
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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 HK$1,059
HK$2,785 total
includes taxes & fees
20 Sept - 21 Sept
Quaint Bungalow, near Great Lakes Naval Base
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

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 HK$1,740
HK$3,995 total
includes taxes & fees
30 Sept - 1 Oct
Spacious 4BR near Northwestern with King Beds + Crib
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, (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 HK$1,245
HK$2,548 total
includes taxes & fees
20 Sept - 21 Sept
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Clean room, funky smell tho. Super nice staff. Very helpful"
Pedro 1-night trip
Posted 2 hours ago
Congress Plaza Hotel

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
137
Accommodation
779 Vacation Homes
Lowest Price
HK$1,696
Highest Price
HK$8,258

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