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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

Communal lounging

1. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.0 out of 10, Wonderful, (4 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is CA $420
CA $851 total
includes taxes & fees
Oct 24 - Oct 25
Cozy Studio Suite, Steps from River North & Shops
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

2. 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 CA $372
CA $1,146 total
includes taxes & fees
Oct 26 - Oct 27
Theater • Game Room • Gym • Firepit • 4BR Home
A bedroom with a bed, a white door, and a mounted television on the wall.

3. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is CA $286
CA $1,100 total
includes taxes & fees
Oct 20 - Oct 21
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A modern living room with a sectional sofa, a coffee table, and a TV.

4. 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 $255
CA $328 total
includes taxes & fees
Oct 20 - Oct 21
Attractive Coach House Apartment for rent in Oak Park.
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is CA $181
CA $434 total
includes taxes & fees
Oct 21 - Oct 22
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

6. 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 CA $491
CA $1,009 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.

7. 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 CA $297
CA $1,441 total
includes taxes & fees
Oct 22 - Oct 23
Sleeps 18 • 8BR • Game Room • Gym • Theater
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 CA $301
CA $534 total
includes taxes & fees
Nov 11 - Nov 12
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Room

9. 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 CA $248
CA $1,159 total
includes taxes & fees
Oct 18 - Oct 19
Arcade • Theater • Gym • Office • Sleeps 15
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

10. 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 CA $152
CA $296 total
includes taxes & fees
Oct 27 - Oct 28
Master qtr close to nature & easy urban facilities
A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

11. 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 CA $474
CA $1,023 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.

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, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is CA $211
CA $430 total
includes taxes & fees
Oct 20 - Oct 21
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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 CA $241
CA $387 total
includes taxes & fees
Oct 28 - Oct 29
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

14. 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 $272
CA $691 total
includes taxes & fees
Oct 27 - Oct 28
Classic Forest Park Foursquare < 1 Mi to Blue Line
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

15. 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 traveller
The price is CA $255
CA $530 total
includes taxes & fees
Oct 26 - Oct 27
LUXE 3 BR, 2 BA + Hot Tub
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

16. 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 CA $254
CA $515 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Home by O'Hare + EV Plug
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

17. 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.
Spacious 4BR near Northwestern with King Beds + Crib
A two-story house with a garage, solar panels, and a red car parked in front.

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

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is CA $176
CA $554 total
includes taxes & fees
Oct 23 - Oct 24
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.

19. 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 CA $748
CA $2,735 total
includes taxes & fees
Nov 2 - Nov 3
Premier 9BR Art Deco manor with garage.
A building with a sign reading 'Hale Street Cantina' and a brick facade.

20. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (74 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is CA $255
CA $462 total
includes taxes & fees
Oct 20 - Oct 21
✽ Charming Cottage ✽ close to College/Town/Station
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Room smelled so clean and fresh! Our room size was perfect for our stay. Staff was super nice and helped a lot. I did wish a microwave was available in the room. Location was great - nearby stores, cafes and a good bagel spot. Neighborhood was safe and secure. Would recommend the hotel for future stays."
Kanae 2-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
334
Accommodation
744 Vacation Homes
Lowest Price
CA $296
Highest Price
CA $2,735

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