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Vacation Homes in Chicago Station

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

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

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

8.0 out of 10, Very Good, (5)
"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
10.0 out of 10, Exceptional, (6)
"This house was in a really convenient location - relatively close to the airport and within walking distance of downtown Bucktown. The home was very clean, the beds were really comfortable (not always the case in vacation rentals!), the communication was thorough and quick. It was perfect for me and my 3 friends!"
Chic and Spacious Bi-level 3BD in Bucktown!

Wicker Park Haven. 3-Levels. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage

10.0 out of 10, Exceptional, (23)
"Nancy was a great host and she place was even better!"
Wicker Park Haven. 3-Levels. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.2 out of 10, Wonderful, (17)
"Very quiet and close to CTA , Old Town easy access to the city"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS

8.6 out of 10, Excellent, (7)
"For friends traveling to Chicago this is the perfect layout for privacy, modern amenities and a wonderful place to relax. Highly recommend for its location and accommodation."
MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS

Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

9.0 out of 10, Wonderful, (6)
"Very convenient to the Metra blue line, lots of bars and restaurants in the neighborhood. "
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (49)
"We stayed for a number of weeks at the property - it was an excellent stay! The property is exactly as advertised and the owner was extremely helpful, communicative, and responsive throughout. The house is modern, in good condition, and is an excellent location."
Luxury House in the heart of Old Town with Parking

Spacious 5 BR / King Size Beds + Private Parking!

9.6 out of 10, Exceptional, (13)
"The place was wondeful and the host was very easy to communicate with and prompt in his responses. 10/10 would stay here again!"
Spacious 5 BR / King Size Beds + Private Parking!

Spacious and Sleek 4BD/2.5BA - Logan Square!

9.2 out of 10, Wonderful, (21)
"Overall, we had a great time in Chicago. The area was perfect and it’s located right across a school so it made it a bit more entertaining when seating out in the balcony. The home had all we looked for and was very much pretty clean. Nice place to stay and will definitely reconsider for our next stay. "
Spacious and Sleek 4BD/2.5BA - Logan Square!

5 BR / 3.5 BA Newly Built Home in Logan Square!

8.4 out of 10, Very Good, (15)
"The house was in a great location for accessing great restaurants and entertainment in Chicago. The house was clean and had a well-functioning kitchen."
5 BR / 3.5 BA Newly Built Home in Logan Square!

Spacious 4-Level/4-Bedroom Townhouse in West Loop

10.0 out of 10, Exceptional, (57)
"Excellent property, excellent location, excellent host!"
Spacious 4-Level/4-Bedroom Townhouse in West Loop

GROUP LUX LINCOLN PARK 4BD/4.5BA Home +parking

9.6 out of 10, Exceptional, (4)
"What a wonderful experience we had. We were a group of 7 girlfriends, some traveling to Chicago for the first time. We have been friends forever, since 1st grade for most, and we wanted a place close to everything but with enough space to catch up. This property was excellent. Townhouse with two apartments that connected in fun and quirky ways. We joked we needed a map... getting to that age lol It was very clean, with enough beds for all, appreciated the multiple bathrooms! The home was...
GROUP LUX LINCOLN PARK 4BD/4.5BA Home +parking

Vital Urban: Spa Inspired Retreat

10.0 out of 10, Exceptional, (6)
"All the comforts of home with the amenities of a resort! Communication with the host was stellar. We had an amazing stay and look forward to booking again!"
Vital Urban: Spa Inspired Retreat

Fantastic Home in Wicker Park

10.0 out of 10, Exceptional, (12)
"Beautiful house in a lively neighborhood, had a great time."
Fantastic Home in Wicker Park

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

10.0 out of 10, Exceptional, (2)
"Spacious and clean property in a great location. "
Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Chicago West Town Row House

2.0 star property
9.4 out of 10, Exceptional, (3)
"Would use this property again, was very cute and interesting lay out. "
Chicago West Town Row House

Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover

10.0 out of 10, Exceptional, (2)
"My new go to spot to stay in Chicago. Really loved the space and location, easy to get around. "
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover

Spacious Townhome! 3 bedrooms & 2 complete bath and 2 outdoor Patios, Near Train

10.0 out of 10, Exceptional, (16)
"We had a great stay here. Really added to our enjoyment of Chicago. Marco is a great host. The place is very comfortable."
Spacious Townhome! 3 bedrooms & 2 complete bath and 2 outdoor Patios, Near Train

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (6)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
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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