West Side Vacation Rentals

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Vacation Rentals in West Side

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (257)
"It was wonderful!"
The price is CA $160
CA $188 total
includes taxes & fees
Mar 20 - Mar 21
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (140)
"My unit was very nice and more than perfect for my needs. It was spacious and quiet. There is little going on in the area in the evenings which I found a bit unnerving as an older adult. You know - there's safety in numbers! "
The price is CA $178
CA $209 total
includes taxes & fees
Feb 28 - Mar 1
Sonder The Burnham Apartments

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (130)
"I love it"
The Neighborhood Hotel-Little Italy

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (40)
"I loved how easy it was to find and the instructions to access was easy to follow"
The price is CA $179
CA $210 total
includes taxes & fees
Mar 13 - Mar 14
Sonder Greektown

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (222)
"I’ve stayed at this host’s properties several times, and the places are all lovely and welcoming with lots of extra touches and conveniences!"
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

8.8 out of 10, Excellent, (23)
"Great place to stay, close to downtown. Clean comfortable beds. "
Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (167)
"Was in a great location. Everything seemed new and put together well. Great stay and was nice to watch it's snow, from inside! "
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (155)
"We love this well stocked condo. The location, off street parking and amenities make it a great home away from home for us. "
NEW LUXURY CONDO WITH PATIO DECK

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (33)
"Beautiful apartment! We really enjoyed our time in Chicago. We ended up just parking across the street. It was easier, and there was always a spot available. There are many stairs leading up to the third floor apartment, so keep that in mind if you have mobility issues. The host texts you right back if you have concerns or questions."
Remodeled West Loop Apartment Near United Center

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

10.0 out of 10, Exceptional, (275)
"In town for an event, the amenities and neighbourhood were very nice, the only down side was the noise considering that a we had early morning obligations"
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

ART Downtn Fulton Market-3 bdrm HOME-EVTesla Private Grge-Sleeps 10-Rooftop-Pets

10.0 out of 10, Exceptional, (1)
"My family and I had a wonderful weekend in Chicago, all thanks to your beautiful home. We comfortably slept four people and enjoyed the ample space. The house is filled with stunning natural light during the day, thanks to the full windows on the second floor and a skylight in the stairwell leading to the third floor. One of the features we loved the most was the parking and the use of the garage. The kitchen was easy to navigate, and we appreciated the selection of coffee available."
ART Downtn Fulton Market-3 bdrm HOME-EVTesla Private Grge-Sleeps 10-Rooftop-Pets

Chic Chicago Retreat 2 Bedroom Home by RedAwning

3.0 star property
Chic Chicago Retreat 2 Bedroom Home by RedAwning

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

FIVE STAR Single Family in Heart Of Chicago! Super clean, Great Neighborhood

10.0 out of 10, Exceptional, (84)
"Great trip. On night one, we had a very easy check-in considering we all arrived 10pm or later and at 3 different times.On night two, we commuted easily and inexpensively to Wrigley Field for an awesome game. On our final night, we found a casino within a few miles.After checking out, we were able to do some amazing shopping before heading home.Overall this was a great trip in a great residence."
FIVE STAR Single Family in Heart Of Chicago! Super clean, Great Neighborhood

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"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

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (13)
"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."
Experience Chicago living near United Center

Entire Below Level Studio w/ Private Sauna

10.0 out of 10, Exceptional, (31)
"We loved the area and the place was easy to navigate as well as clean. LOVE the sauna. We will definitely be reaching back out when we visit in the spring."
Entire Below Level Studio w/ Private Sauna

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (12)
"Overall for solo travel is recommended."
Ground Floor Studios in Chicago by 747 Lofts

Luxuriant, Foodie, Culture,

9.6 out of 10, Exceptional, (10)
"Great property! Great kitchen for making our Thanksgiving feast. Loved the quiet area and ease of getting to places. Tall windows in the living room let in a lot of light - could use some sort of light filtering shades. Additionally - beds had only a sheet and a thin blanket. Glad that we brought an extra blanket with. "
Luxuriant, Foodie, Culture,

Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!

9.8 out of 10, Exceptional, (79)
"Great location - convenient to two L-stops, large park down the street, and good, inexpensive restaurants nearby. Perfect for short stay."
Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!
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 types of properties in West Side you may be interested in

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.6 out of 10, Excellent, (1004)
"Great, friendly staff. Very comfortable beds."
The price is CA $142
CA $167 total
includes taxes & fees
Feb 24 - Feb 25
Crowne Plaza Chicago West Loop by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.0 out of 10, Very good, (1002)
"No complaints. This is coming from a person that’s hard to please."
The price is CA $142
CA $167 total
includes taxes & fees
Feb 27 - Feb 28
Holiday Inn & Suites Chicago - Downtown by IHG

The Emily Hotel

4.0 star property
9.0 out of 10, Wonderful, (1009)
"Van at the front desk was very helpful! "
The price is CA $269
CA $316 total
includes taxes & fees
Mar 9 - Mar 10
The Emily Hotel
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.