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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chicago holiday homes

A brick building with a sign for 'Irish Declans' Pub' and outdoor seating with metal chairs and tables.

1. Scott C.H.

Scott C.H.
2.0 star property
Near North Side
The price is HK$5,950
HK$10,113 total
includes taxes & fees
8 Sept - 9 Sept
Scott C.H.
A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

2. 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$3,190
HK$6,452 total
includes taxes & fees
28 Sept - 29 Sept
Envitae Hotel, 4BR Modern Sleek Apartment
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

3. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
The price is HK$4,139
HK$7,816 total
includes taxes & fees
16 Sept - 17 Sept
ENVITAE Hotel, 4BR Luxury Modern Apartments
A spacious living room with a large sectional sofa, a glass coffee table, and a wooden staircase.

4. Scott C.H. - Chicago Getaway

Scott C.H. - Chicago Getaway
Near North Side
The price is HK$7,059
HK$9,722 total
includes taxes & fees
8 Sept - 9 Sept
Scott C.H. - Chicago Getaway
A living room with a sectional sofa, a round wooden coffee table, and three framed artworks on the wall.

5. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
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$1,023
HK$4,696 total
includes taxes & fees
7 Sept - 8 Sept
4BR Retreat w/ Theater, Arcade, Gym and Firepit
A dining room with a large table, four chairs, a vase, and a mirror on the wall.

6. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is HK$1,006
HK$5,067 total
includes taxes & fees
7 Sept - 8 Sept
4 BR • Theater Room • Gym • Walk to Lincoln Park!

7. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.6 out of 10, Exceptional, (4 reviews)
"Really enjoyed staying at this property! Clean and safe. Would recommend!"
United States
Emmeline R.
The price is HK$5,370
HK$9,547 total
includes taxes & fees
18 Sept - 19 Sept
Modern 3BR Apartment Near North Ave Shops
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (6 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$813
HK$6,586 total
includes taxes & fees
8 Sept - 9 Sept
Sleeps 18 • 8BR • Game Room • Gym • Theater

9. 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$826
HK$5,527 total
includes taxes & fees
9 Sept - 10 Sept
Arcade • Theater • Gym • Office • Sleeps 15
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$640
HK$3,521 total
includes taxes & fees
2 Sept - 3 Sept
Game Room • Fire-pit • Playground • Gym • Billiard
A patio area with stone flooring, wicker furniture, and a brick building in the background.

11. Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
South Evanston
9.8 out of 10, Exceptional, (43 reviews)
"The property was in an excellent location; easy walk to beach, beautiful and quiet neighborhood, easy walk to shops. The apartment was clean and spacious. We enjoyed out stay. Only complaint is no TV. We spent much of our time with my daughter who lives nearby but if I had mornings or longer evenings inside, I would have wanted a TV."
United States
debra
The price is HK$1,560
HK$2,626 total
includes taxes & fees
9 Sept - 10 Sept
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

12. 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)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is HK$1,164
HK$2,386 total
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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$1,383
HK$2,579 total
includes taxes & fees
22 Sept - 23 Sept
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern living room with a sectional sofa, a coffee table, and a TV.

14. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.0 out of 10, Very good, (3 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$1,411
HK$1,849 total
includes taxes & fees
8 Sept - 9 Sept
Attractive Coach House Apartment for rent in Oak Park.
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

15. 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$1,440
HK$3,537 total
includes taxes & fees
8 Sept - 9 Sept
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.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is HK$1,021
HK$2,427 total
includes taxes & fees
8 Sept - 9 Sept
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

17. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (86 reviews)
"Lovely, quiet property with easy access to retail & restaurants. Perfect for a long weekend away."
United States
Suzanne H.
The price is HK$910
HK$1,720 total
includes taxes & fees
13 Sept - 14 Sept
Master qtr close to nature & easy urban facilities
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

18. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (34 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is HK$765
HK$2,041 total
includes taxes & fees
2 Sept - 3 Sept
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
A circular fire pit with chairs around it, string lights overhead, and a house in the background.

19. 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$1,235
HK$7,285 total
includes taxes & fees
9 Sept - 10 Sept
Sleeps 18 • 7BR • Gym • Game Room • Theater
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

20. 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$1,505
HK$3,816 total
includes taxes & fees
7 Sept - 8 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
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

River Hotel

River Hotel

8/10 Good
"The front desk staff was wonderful and even upgraded my room so I could check in early when I was just expecting to store my bag. I had a wonderful view! The room is cozy and bathroom has good water pressure and fluffy towels. The elevators are quick and quiet. There is a refillable water bottle station by the elevator that I had never seen any where else. The coffee maker in the lounge was out of order when I was there. The Nespresso maker in my room wasn't working right either but with enough pushing and adjusting I was able to get it to function There is no restaurant or bar in the building but there is one on either side and probably a dozen options within two blocks. The location is great- close to Michigan Avenue, the River Walk and Millennium Park. This was my second stay and won't be my last."
Kim 1-night trip
Posted 1 hour ago
River Hotel

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
241
Accommodation
779 Vacation Homes
Lowest Price
HK$1,720
Highest Price
HK$9,547

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