A wooden dock extending into a calm body of water, with boats docked nearby and a building with a red roof in the background.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Kenilworth vacation homes

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

1. 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 AED 437
AED 810 total
includes taxes & fees
19 Oct - 20 Oct
Master qtr close to nature & easy urban facilities
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 AED 566
AED 2,906 total
includes taxes & fees
5 Oct - 6 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

3. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
Chicago Riverhouse with private fenced in oasis
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

4. 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 AED 635
AED 2,481 total
includes taxes & fees
13 Oct - 14 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

5. 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 AED 758
AED 3,678 total
includes taxes & fees
5 Oct - 6 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

6. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (24 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 AED 523
AED 1,165 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Home by O'Hare + EV Plug
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

7. 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 AED 407
AED 1,888 total
includes taxes & fees
6 Oct - 7 Oct
Game Room • Fire-pit • Playground • Gym • Billiard
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

8. 6 Kings Ping-Pong Gazebo!

6 Kings Ping-Pong Gazebo!
Northbrook
9.0 out of 10, Wonderful, (7 reviews)
"Hosts were great. Very accommodating to our needs and quick to respond. I will stay again!"
United States
Cj Y.
The price is AED 1,138
AED 2,494 total
includes taxes & fees
4 Oct - 5 Oct
6 Kings Ping-Pong Gazebo!
A modern kitchen with white cabinets, a black stove, and a microwave.

9. Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (83 reviews)
"It was a very clean place, comfortable furniture and beds e.c.t."
United States
Ronald H.
The price is AED 698
AED 1,257 total
includes taxes & fees
29 Oct - 30 Oct
Your Next Vacation Home
Room

10. Great 6 bedroom home near Chicago still avoiding the traffic of the big city

Great 6 bedroom home near Chicago still avoiding the traffic of the big city
Des Plaines
Great 6 bedroom home near Chicago still avoiding the traffic of the big city
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

11. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (44 reviews)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
The price is AED 1,128
AED 2,389 total
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A single-story house with a covered porch, a front door, and a small garden area.

12. 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 AED 698
AED 1,257 total
includes taxes & fees
6 Oct - 7 Oct
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.

13. 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 AED 661
AED 854 total
includes taxes & fees
4 Oct - 5 Oct
Attractive Coach House Apartment for rent in Oak Park.
A modern kitchen with stainless steel appliances, grey cabinetry, and pendant lighting.

14. 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 AED 845
AED 1,876 total
includes taxes & fees
5 Oct - 6 Oct
AeroStay Retreat – 4BR Home Near O’Hare Airport!
A modern hotel room with a bed, a sofa, a coffee table, a TV, and artwork on the wall.

15. Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Irving Park
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

16. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is AED 1,322
AED 3,250 total
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A white two-story house with a porch, steps, and a small table with chairs.

17. 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 AED 1,084
AED 2,447 total
includes taxes & fees
6 Oct - 7 Oct
Oak Park Victorian by FLW Studio
A modern kitchen with white cabinetry, a central island with bar stools, a stove, oven, microwave, and a ceiling fan.

18. Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Libertyville
The price is AED 503
AED 2,238 total
includes taxes & fees
5 Oct - 6 Oct
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

19. 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 AED 545
AED 1,083 total
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

20. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is AED 917
AED 3,087 total
includes taxes & fees
5 Oct - 6 Oct
4 BR • Theater Room • Gym • Walk to Lincoln Park!
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 Kenilworth Hotel Reviews

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Everything was awesome love this place"
Jared 2-night trip
Posted 1 hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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