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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chicago vacation homes

A kitchen with a built-in counter, pendant lights, and decorative wall art.

1. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
4 BR • Theater Room • Gym • Walk to Lincoln Park!
Communal Lounge

2. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (31 reviews)
"This was a great property. It was easy to access, easy transportation near by, Whole Foods is right around the corner and the neighborhood is very pleasant. Will definitely stay here again."
United States
Josh
The price is ￥42,349
￥99,059 total
includes taxes & fees
Oct 19 - Oct 20
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
A compact laundry area with a front-loading washer and dryer, wooden cabinets above, and a tiled floor.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ￥17,588
￥44,764 total
includes taxes & fees
Oct 19 - Oct 20
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Room

4. 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 ￥24,333
￥126,201 total
includes taxes & fees
Oct 21 - Oct 22
Arcade • Theater • Gym • Office • Sleeps 15
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

5. 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, (45 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 ￥49,618
￥102,375 total
includes taxes & fees
Oct 29 - Oct 30
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
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, (10 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 ￥29,082
￥154,700 total
includes taxes & fees
Oct 22 - Oct 23
Sleeps 18 • 8BR • Game Room • Gym • Theater
A laundry room with two front-loading LG washing machines.

7. Tranquil 3-bedroom house with AC in charming Wheaton, Illinois

Tranquil 3-bedroom house with AC in charming Wheaton, Illinois
Wheaton
The price is ￥52,336
￥83,768 total
includes taxes & fees
Oct 29 - Oct 30
Tranquil 3-bedroom house with AC in charming Wheaton, Illinois
A single-story house with a covered porch, a front door, and a small garden area.

8. 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 ￥30,861
￥55,228 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

9. 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 ￥30,340
￥76,242 total
includes taxes & fees
Oct 27 - Oct 28
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

10. 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 ￥45,668
￥103,739 total
includes taxes & fees
Oct 21 - Oct 22
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

11. 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)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is ￥23,466
￥47,757 total
includes taxes & fees
Oct 19 - Oct 20
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

12. 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.
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.

13. 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 ￥26,863
￥42,537 total
includes taxes & fees
Nov 9 - Nov 10
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern office with a black desk, two chairs, a large window with blinds, a plant, and a ceiling light fixture.

14. Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport

Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport
Belmont Cragin
The price is ￥37,925
￥102,331 total
includes taxes & fees
Nov 16 - Nov 17
Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

15. 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 ￥41,992
￥128,859 total
includes taxes & fees
Oct 26 - Oct 27
Theater • Game Room • Gym • Firepit • 4BR Home
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

16. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is ￥28,444
￥58,830 total
includes taxes & fees
Oct 26 - Oct 27
LUXE 3 BR, 2 BA + Hot Tub
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, (88 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is ￥16,924
￥32,841 total
includes taxes & fees
Oct 27 - Oct 28
Master qtr close to nature & easy urban facilities
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

18. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (26 reviews)
"We enjoyed our 2 night stay. The home was exactly what we were expecting. It is on a quiet street and is within walking distance to several restaurants. The beds were comfortable and and the lower level bathroom was especially nice to get ready in."
United States
KIM K.
The price is ￥23,545
￥51,729 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Home by O'Hare + EV Plug
A two-story house with a garage, solar panels, and a red car parked in front.

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

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is ￥19,626
￥60,825 total
includes taxes & fees
Oct 19 - Oct 20
Lombard 1BR & 1BH Suite Close to freeway & Mall
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

20. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is ￥87,227
￥309,763 total
includes taxes & fees
Nov 18 - Nov 19
Premier 9BR Art Deco manor with garage.
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
"Room is spacious, very clean hotel. I would recommend."
Ramesh 4-night trip
Posted 13 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
285
Accommodation
744 Vacation Homes
Lowest Price
￥32,841
Highest Price
￥309,763