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Vacation Homes in Chicago

Stylish 3bd w/ backyard patio mins from Downtown!

2.0 star property
8.8 out of 10, Excellent, (3)
"Very comfortable home. Location was great. Owners were very responsive and helpful. A storm on our last day unfortunately left us without power, owner was great at keeping us informed of status. Already went to book for our next trip but someone beat us to it. "
Stylish 3bd w/ backyard patio mins from Downtown!

Your Next Vacation Home

9.6 out of 10, Exceptional, (48)
"Very clean and tidy. We didn't stay long, just slept overnight before heading out again, but the rooms were comfortable."
$363 nightly
The price is $367
Jul 14 - Jul 15
Total includes taxes and fees
Your Next Vacation Home

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

10.0 out of 10, Exceptional, (16)
"This is a great place and very pet friendly. Only negatives were lack of hashtags (only one in the home), no hair dryer when it advertised it had one, and no TV in any of the bedrooms. The home was clean, spacious, fireplace and hot tub are a great bonus."
Cozy 3-bedroom house in family-oriented Melrose Park.

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (30)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (43)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

10.0 out of 10, Exceptional, (11)
"Lots of good food and close to transit! Amazing little spot."
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

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

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

Charming 3-bedroom house with WiFi in peaceful Hazel Crest

8.0 out of 10, Very Good, (4)
"The property was very spacious and clean and customer service is very responsive and quick. "
$342 nightly
The price is $345
Jul 13 - Jul 14
Total includes taxes and fees
Charming 3-bedroom house with WiFi in peaceful Hazel Crest

Des Plaines Vacation Rental w/ Spacious Backyard!

8.6 out of 10, Excellent, (12)
"The home was very clean and exactly as pictured. We had a lovely stay."
Des Plaines Vacation Rental w/ Spacious Backyard!

3-bedroom house in awesome Addison with WiFi, AC. Enjoy your stay

7.6 out of 10, Good, (5)
"Wonderful neighborhood! Comfortable beds! Great TV in the living room. Communication with host was fabulous. "
$434 nightly
The price is $434
Jul 13 - Jul 14
Total includes taxes and fees
3-bedroom house in awesome Addison with WiFi, AC. Enjoy your stay

Cozy Home | King Bed | 10P | Metra | Chicago Suburb

9.8 out of 10, Exceptional, (9)
"The house worked perfectly for our stay. Lots of seating options and a beautiful kitchen for home prepped meals. The house also gets amazing natural light with the abundance of windows."
Cozy Home | King Bed | 10P | Metra | Chicago Suburb

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (43)
"The place was located right down the street from where the concert was at. Cute place, better than a hotel, parking right outside the place. "
Belmont House, Classy & Chic/walk to Wrigley Field

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (40)
"The large number of bedrooms provides privacy for a lot of people."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Lincoln Park Living - Suite 1

9.4 out of 10, Exceptional, (26)
"Great location in a beautiful part of town. Walk to Wrigley. Place was great for 2 families to hang out. "
Lincoln Park Living - Suite 1

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.6 out of 10, Exceptional, (7)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

2.0 out of 10, (1)
"Here is a condensed version of the document, aiming for around 1500 characters:Review of rental: Communication was good, but the house was problematic. It looked abandoned with overgrown shrubs and a "Beware of Dog" sign. Jessica, the host, was finishing cleaning upon arrival due to a late checkout. The living room had an 85" TV but only one lamp with no shade. One couch was broken. The dining room had a table and a makeshift hutch. The kitchen was odd with mismatched items; no coffee pot for...
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

9.6 out of 10, Exceptional, (166)
"Great location. Has everything we needed. Great host. Have already recommended it to others who visit Chicago frequently and will definitely stay there again. "
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

10.0 out of 10, Exceptional, (2)
"The area is quiet and the apartment is close to a dog park which is open to non-residents. There is a paved walkway right by the park that’s nice so I was able to walk my dog in the morning. The property manager immediately replied to any questions I had and the apartment was fully stocked in the kitchen, etc. I booked this because of the cost. I was in town to see the Indiana Dunes. I would stay here again."
$165 nightly
The price is $167
Jul 16 - Jul 17
Total includes taxes and fees
Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

Chic Oasis/Game Room/Near Base/5 Bedroom

2.0 star property
10.0 out of 10, Exceptional, (3)
"This was a great experience. Marta was great to work with and responded quickly to my questions before and during the stay. The house was clean and had everything we needed for our stay. The kids enjoyed the games and separate space in the basement. "
Chic Oasis/Game Room/Near Base/5 Bedroom

Cozy 2 bedroom house/w garage in Skokie

10.0 out of 10, Exceptional, (11)
"The house was super nice, the pictures do not do it justice. Great location, nice neighborhood."
Cozy 2 bedroom house/w garage in Skokie
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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