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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 891 Vacation Homes in Chicago with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (30)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Aerial view

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

10.0 out of 10, Exceptional, (166)
"We stayed here for my sister’s bachelorette. Location was great and the space was huge, perfect for our big group."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (23)
"Liked very much"
Cozy Home Sweet Homewood.
Modern 3Bd Townhome Near Beach & Base
Outdoor dining

Modern 3Bd Townhome Near Beach & Base

9.8 out of 10, Exceptional, (20)
"This property was exactly what we were needing! Cute house, very well maintained and the leasing agents were responsive to any concerns. "
Modern 3Bd Townhome Near Beach & Base
Cozy 3-bedroom house in family-oriented Melrose Park.
Interior

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (9)
"Good house with 3 bedrooms. 1.5 bathrooms. The hot tub is a nice touch. Just your average house, nothing extravagant. Had towels and all. Netflix etc. was overall a pleasant stay. "
Cozy 3-bedroom house in family-oriented Melrose Park.
Updated Forest Park 3 BR Bungalow
Fridge, microwave, oven, stovetop

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (102)
"This home sparkled; it was so clean! Also, it's very thoughtfully furnished and was in walking distance of shopping, restaurants, and public transportation for me! I hope to stay here again, soon!"
Updated Forest Park 3 BR Bungalow
Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East
Fridge, microwave, oven, stovetop

Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East

10.0 out of 10, Exceptional, (4)
"This property was great for our group! It was clean and ready to use when we got there. There was even snacks left out for us! "
Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Fridge, microwave, oven, stovetop

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.2 out of 10, Wonderful, (90)
"Good for our get together."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Charming ModernRetro Home!
Smart TV

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (14)
"The house was in a nice neighborhood that was close to a lot of different things. The house was stocked with everything needed for an enjoyable stay. The beds were very com, the home was clean, and the host was very responsive."
Charming ModernRetro Home!
Historic home with easy access to Chicago
Exterior

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (164)
"Beautiful, clean, and comfortable! Perfect getaway and wonderful memories were made!"
Historic home with easy access to Chicago
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Fridge, microwave, oven, dishwasher

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (12)
"We have a good time in this property. It is very well located to go to the United Center and to downtown Chicago."
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!
Fridge, microwave, oven, stovetop

2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

9.4 out of 10, Exceptional, (18)
"We enjoyed a 3-day stay as we visited Chicago museums for 2 days. Everything went smoothly and we enjoyed our time. If I had to identify room for improvement it would be a more detailed instruction of controlling the furnace thermostat. It warms up very quickly in the house! Otherwise, all was great!"
2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!
Berwyn Beauty
Fridge, microwave, oven, stovetop

Berwyn Beauty

10.0 out of 10, Exceptional, (15)
"We had an amazing time at the Berwyn Beauty. Good location and response time to messages! We Came down for Americas Beauty show and had the most amazing time. "
Berwyn Beauty
BoHo House - A Chic, 1903 Chicago Workers Cottage
Outdoor dining

BoHo House - A Chic, 1903 Chicago Workers Cottage

10.0 out of 10, Exceptional, (10)
"Well located, comfortable and stylish home. The backyard was great to let the dog out and would be a fabulous place to hang out in warmer weather. Perfectly clean throughout, and great host communication made for a wonderful stay."
BoHo House - A Chic, 1903 Chicago Workers Cottage
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Fridge, microwave, oven, stovetop

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

LUXE 3 BR, 2 BA + Hot Tub

9.0 out of 10, Wonderful, (24)
"This property was is in a good neighborhood nice and clean I really enjoy myself Thanks"
The price is $456
includes taxes & fees
$451 per night
May 4 - May 5
LUXE 3 BR, 2 BA + Hot Tub
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (51)
"Great spot."
The price is $194
includes taxes & fees
$194 per night
Apr 30 - May 1
Master qtr close to nature & easy urban facilities
Private Home Awaits
Fridge, microwave, oven, stovetop

Private Home Awaits

10.0 out of 10, Exceptional, (2)
"Very convenient to all my activities for my 55th Birthday "
Private Home Awaits
Spacious 5-bedroom house with movie room, game room and more!
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house with movie room, game room and more!

10.0 out of 10, Exceptional, (3)
"I wanted a fun place to stay close to friends in Oak Park. We had 2 teenagers and they basically lived in the basement with the games while we stayed here. You can hear them talking in the basement while on the main level. The location was good for our needs."
Spacious 5-bedroom house with movie room, game room and more!
Family frndly TwnHm by navy base
Fridge, microwave, oven, stovetop

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (13)
"This property was easy to get to and close to all amenities, including the Navy RTC. Host was excellent! Responsive and ensured we had everything we needed. Property was very clean and beds were comfortable. Easy check-in and out process. Great experience overall!"
Family frndly TwnHm by navy base
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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Other property types in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (737)
"Wonderful stay, beautiful views, spacious and clean!"
The price is $188
includes taxes & fees
$160 per night
Apr 30 - May 1
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (484)
"Good place"
The price is $135
includes taxes & fees
$115 per night
May 26 - May 27
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (277)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is $160
includes taxes & fees
$137 per night
May 26 - May 27
Sonder Market Hall
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.