Search Vacation Homes in Chicago Halsted Station

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 265 Vacation Homes in Chicago Halsted Station with updated reviews, rates, and availability.

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

8.4 out of 10, Very Good, (6)
"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

Luxury Modern home minutes from Downtown Chicago

10.0 out of 10, Exceptional, (13)
"Great location. Great communication with host. Great property. Great all around stay!"
Luxury Modern home minutes from Downtown Chicago

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (12)
"House was clean and the check in process was easy. The gated driveway easily fit 3 cars with room to spare."
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

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 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

Luxe Single Family Home + Private Skyline Rooftop! Sleeps 10

9.8 out of 10, Exceptional, (8)
"Caitlin is a wonderful host and very communicative. The rooftop is a great space to lounge around and hang out and the house has plenty of room for a large group. If you aren't able to do stairs, be warned! Otherwise, strongly recommend this place. Great neighborhood, lovely home, and had a wonderful time with my family. "
Luxe Single Family Home + Private Skyline Rooftop! Sleeps 10

Chicago West Town Row House

2.0 star property
9.0 out of 10, Wonderful, (2)
"Would use this property again, was very cute and interesting lay out. "
Chicago West Town Row House

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (5)
"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

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

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (48)
"The space was as promised. Well furnished, clean, and comfortable. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

Downtown Goose Island with access to patio - 1

9.2 out of 10, Wonderful, (5)
"Tuvimos una estancia muy buena en este departamento. Está muy cerca de las principales atracciones de Chicago y tiene acceso inmediato a la vía express que recorre toda la ciudad. Muy apto para ir y regresar al aeropuerto O’Hare. Sus instalaciones fueron confortables y limpias y las indicaciones de los servicios fueron muy buenas y sencillas. Sin duda regresaríamos para aprovechar más el verano e invierno. *****"
Downtown Goose Island with access to patio - 1

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

9.8 out of 10, Exceptional, (19)
"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

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!

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

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

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

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

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

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

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

10.0 out of 10, Exceptional, (90)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

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

9.8 out of 10, Exceptional, (21)
"Beautiful home in great location. Host was very responsive and we had no issues "
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center

Level studio suite with full kitchen and luxury bath

10.0 out of 10, Exceptional, (1)
"This was my first time staying at a Level property, and I was really impressed. I loved the studio; it felt like a one-bedroom because of the wall between the bed and the living area. And it was just as spacious and light-filled as the photos showed! I would gladly stay here again. It's a little more expensive than staying inside the loop, but the neighborhood was quieter and nicer, so it was worth it to me."
Level studio suite with full kitchen and luxury bath
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.
Save an average of 15% on thousands of hotels when you're signed in