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15 Aug - 17 Aug
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Vacation Homes in Chicago Halsted Station

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Iron/ironing board, WiFi, bed sheets

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Exterior

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (15)
"The house was excellent for our family. It was definitely enough room and everything was okay for our trip. Neighborhood was nice and no one bothered us. "
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Secure, Quiet, Solo Traveler's Fave, Free Coffee!
Exterior detail

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
Fridge, microwave, oven, stovetop

EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

9.8 out of 10, Exceptional, (20)
"Beautifully maintained property in residential neighborhood proximate to fantastic food and beverage / public transportation and quick cab ride from all major Chicago attractions. "
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
Spacious 4-Level/4-Bedroom Townhouse in West Loop
Fridge, microwave, oven, stovetop

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
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
Property grounds

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
Spacious 5 BR / King Size Beds + Private Parking!
Property grounds

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!
The Neighborhood Hotel - Little Italy One Bedroom
Exterior detail

The Neighborhood Hotel - Little Italy One Bedroom

9.6 out of 10, Exceptional, (4)
"I would quickly recommend this listing to any friend of mine- it was a highlight of the vacation! The location is a bit outside of the heart of downtown, but is easily accessible by a 30-40 min safe walk. Clean, stylish, safe, and very comfortable. Thanks for a great stay!"
The Neighborhood Hotel - Little Italy One Bedroom
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Exterior

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (90)
"We stayed at the property for a bachelorette party weekend. The house was very nice and the host was so accommodating! The coffee maker was also a big plus. Highly, highly recommend for a large group! Great stay! "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Downtown Goose Island with access to patio - 1
Fridge, microwave, oven, stovetop

Downtown Goose Island with access to patio - 1

9.0 out of 10, Wonderful, (6)
"Perfect location for a visit with our son. "
Downtown Goose Island with access to patio - 1
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Property grounds

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (50)
"We enjoyed the convenience and location. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS
Interior

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

9.0 out of 10, Wonderful, (9)
"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
7-Bedroom 2-Flat Perfect for Groups — Near Train, Expressway, United Center
Outdoor dining

7-Bedroom 2-Flat Perfect for Groups — Near Train, Expressway, United Center

10.0 out of 10, Exceptional, (1)
"This place really can accommodate a large group. Great location, close to public transport, Ubers not too bad from here and parking is good. Host was very responsive to any questions. "
7-Bedroom 2-Flat Perfect for Groups — Near Train, Expressway, United Center
Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1
4 bedrooms, desk, iron/ironing board, travel crib

Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1

10.0 out of 10, Exceptional, (30)
"Such a great place!!!! Would 100% stay her again!"
Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1
The Banksy-King Bed-Firepit-Rooftop-United Center
Terrace/patio

The Banksy-King Bed-Firepit-Rooftop-United Center

10.0 out of 10, Exceptional, (1)
The Banksy-King Bed-Firepit-Rooftop-United Center
Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!
Fridge, microwave, stovetop, dishwasher

Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!

9.0 out of 10, Wonderful, (8)
"We had a great stay! This was an awesome spot for a large group to stay near downtown Chicago!"
Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!
Luxury Modern home minutes from Downtown Chicago
3 bedrooms, in-room safe, desk, iron/ironing board

Luxury Modern home minutes from Downtown Chicago

10.0 out of 10, Exceptional, (15)
"My friends and I love the neighborhood and how the house was perfectly set up for cosy conversation and hanging out. "
Luxury Modern home minutes from Downtown Chicago
Chic ART+1700sqf +3BR Home360° Roof+HotTub+CarGarage+12Guests
Fridge, microwave, oven, stovetop

Chic ART+1700sqf +3BR Home360° Roof+HotTub+CarGarage+12Guests

10.0 out of 10, Exceptional, (1)
Chic ART+1700sqf +3BR Home360° Roof+HotTub+CarGarage+12Guests
Chicago West Town Row House
Microwave, oven, stovetop, dishwasher

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
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center
Fridge, microwave, oven, stovetop

Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center

9.8 out of 10, Exceptional, (22)
"Loved the property and location. The host was very communicative and accommodating. Would stay here again!"
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center
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 Halsted Station Hotel Reviews

The Wade

The Wade

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ We had an absolutely wonderful stay! From the moment we arrived, the staff was warm, welcoming, and eager to help with anything we needed. Our room was spotless, comfortable, and had amazing views of the city. The location was perfect—walking distance to so many Chicago attractions, great restaurants, and shopping. The amenities were top-notch, and the attention to detail really made our trip extra special. We can’t wait to come back and would recommend this hotel to anyone visiting Chicago!"
Alexandra 5-night trip
Posted 8 hours ago
The Wade