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, (208)
"Easiest check in and check out process "
The price is CA $77
CA $91 total
includes taxes & fees
Dec 22 - Dec 23
Sonder Market Hall

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"Very convenient location, the apartment was impeccable "
The price is CA $194
CA $228 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Burnham Apartments

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

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (12)
"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "
Experience Chicago living near United Center

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (33)
"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...
The price is CA $221
CA $260 total
includes taxes & fees
Dec 17 - Dec 18
Sonder Greektown

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Overall for solo travel is recommended."
Ground Floor Studios in Chicago by 747 Lofts

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (151)
"Another wonderful Friendsgiving in a beautiful condo. Perfect kitchen for this. "
NEW LUXURY CONDO WITH PATIO DECK

Stay in “STYLE” Apartment, close to CHI downtown

9.8 out of 10, Exceptional, (69)
"Clean space. Neighborhood felt safe. Beds are super hard though so not ideal for everyone. Also the blinds in the bedrooms don’t block out light very well so be prepared to be up when the sun is up if you stay here"
Stay in “STYLE” Apartment, close to CHI downtown

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (118)
"Great location walking distance of restaurants and some nightlife. Good neighborhood very safe college kids walking the streets not occasion. Are you really lazy lots of amenities more than usual in places like this and enjoyed our state would stay there again"
1F Chicago's Little italy Graystone nearDowntown

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

10.0 out of 10, Exceptional, (211)
"Enough room for 2 kids and parents qith room to spare"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place

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

10.0 out of 10, Exceptional, (264)
"This was a fantastic find. Loved the area - let’s hear it for yummy Italian food! The unit was well stocked with everything a guest might need. Highly recommend!"
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Hidden East Village Gem

9.6 out of 10, Exceptional, (29)
"Perfect spot for a family. Visiting for husband’s conference. Great neighborhood and easy to get to all tourist attractions. Highly recommend. All our needs were anticipated. "
Hidden East Village Gem

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

9.2 out of 10, Wonderful, (17)
"Really nice place and the host was super helpful (he even answered when we called at almost 3 in the morning). It has almost every kitchen utensils except for a comal (us mexicans use it a lot lol) "
Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

The Upscale Getaway Near Downtown

9.8 out of 10, Exceptional, (81)
"Alex was helpful in every way possible and the place was perfect in every way and so well appointed "
The Upscale Getaway Near Downtown

Quiet but in the Heart of City walk Everywhere

10.0 out of 10, Exceptional, (3)
"We had an amazing stay. The property was beautiful and having the pool/hot tub was perfect after spending our days walking all over the city. "
Quiet but in the Heart of City walk Everywhere

Cabin 308 by 747 Lofts

9.4 out of 10, Exceptional, (13)
"The property was very clean and has the essentials. Being a 30 second walk from the blue line allowed us to travel most places fairly quickly. It is an ideal location for entertainment and amenities. I would definitely stay again!"
Cabin 308 by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

2.0 star property
8.6 out of 10, Excellent, (10)
"Not bad. Parking around the area wasn't easy, but the location itself was close enough to downtown to be walkable. I would stay again if I were in the area."
River West, Third Floor Chicago by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (5)
"Price and expectations matched "
The price is CA $99
CA $196 total
includes taxes & fees
Dec 1 - Dec 2
Chicago Third Floor Studio by 747 Lofts

Chicago Vacation Rental Apt ~ 7 Mi to Downtown

7.2 out of 10, Good, (7)
"The place was comfortable and inviting. We didn’t have to drive very far to get to downtown Chicago. We enjoyed our stay!"
Chicago Vacation Rental Apt ~ 7 Mi to Downtown
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

The Emily Hotel

4.0 star property
9.0 out of 10, Wonderful, (893)
"Very cool and modern hotel. Staff was very nice and recommended great restaurants in the area. "
The price is CA $242
CA $284 total
includes taxes & fees
Dec 1 - Dec 2
The Emily Hotel

Hotel Chicago West Loop

2.5 star property
8.2 out of 10, Very good, (1011)
"Awesome place! Will stay again. "
The price is CA $165
CA $193 total
includes taxes & fees
Nov 24 - Nov 25
Hotel Chicago West Loop

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (913)
"Great"
The price is CA $182
CA $214 total
includes taxes & fees
Nov 25 - Nov 26
The Hoxton Chicago
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.
Beautiful view of the beach with palm trees

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