West Side Holiday Rentals

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Holiday Rentals in West Side

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (341)
"Great stay!"
The price is AU$228
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (189)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (206)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is AU$269
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Bright & Roomy 4BR in Pilsen

7.8 out of 10, Good, (7)
The price is AU$617
includes taxes & fees
19 Aug - 20 Aug
Bright & Roomy 4BR in Pilsen

Your Perfect 2BR Home w/ Parking

8.0 out of 10, Very good, (4)
"Great location, close to United Center. Our host was super and was able to help me when I couldn't follow the instructions (lol). Wish I could have had a longer stay."
The price is AU$394
includes taxes & fees
3 Sept - 4 Sept
Your Perfect 2BR Home w/ Parking

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"Great location, easy stay!"
The price is AU$382
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Greektown Apartments

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

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

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (16)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is AU$342
includes taxes & fees
17 Aug - 18 Aug
Ground Floor Studios in Chicago by 747 Lofts

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

10.0 out of 10, Exceptional, (302)
"Very clean, nice amenities, excellent designated parking..we have a ford flex...large car. "
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Wicker Pk 2 Bdrm Near Downtown & SaltShed Last Minute Deal 199.00 Aug 17-21

9.8 out of 10, Exceptional, (37)
"Loved the location of the place. Great place to walk to bars and places to eat. Communication with Cheryl was great, parking was no problem at all. "
Wicker Pk 2 Bdrm Near Downtown & SaltShed Last Minute Deal 199.00 Aug 17-21

Experience Chicago living near United Center

9.0 out of 10, Wonderful, (17)
"Clean and cozy . Great communication . Not the best neighborhood but felt secure with passcode locks ! Would stay again "
Experience Chicago living near United Center

Spacious 3-bedroom apartment near downtown, FREE PARKING

8.6 out of 10, Excellent, (4)
"Extremely clean space that was perfect for our group. We didn't spend a lot of time in the home during our stay, but when we did it was fantastic. Only minor gripe would be the upstairs neighbors, they were occasionally quite loud and woke us up a few times in the middle of the night. Would absolutely stay here again, if/when we come back to the area."
The price is AU$562
includes taxes & fees
18 Aug - 19 Aug
Spacious 3-bedroom apartment near downtown, FREE PARKING

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (150)
"This is an awesome place to stay in Chicago."
1F Chicago's Little italy Graystone nearDowntown

4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!

10.0 out of 10, Exceptional, (3)
"We stayed here for 4 days and our stay was awesome. Matthew was super responsive for all our queries. "
4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!

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

10.0 out of 10, Exceptional, (248)
"Well stocked, spacious and beautifully decorated, excellent location, attentive host. We had a great stay!"
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (186)
"A perfect place to stay. The rooftop bar has the BEST views of the city, especially around sunset. I would definitely stay here again! "
NEW LUXURY PENTHOUSE CONDO

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (4)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is AU$351
includes taxes & fees
18 Aug - 19 Aug
Stylish 1BR in West Loop

Your 2BR Home in the City

10.0 out of 10, Exceptional, (1)
"Visited my daughter who lives near by in Ukrainian Village Everything was great! Would definitely stay again "
The price is AU$385
includes taxes & fees
3 Sept - 4 Sept
Your 2BR Home in the City

Upscale 4BR Retreat: Wicker Park

9.0 out of 10, Wonderful, (4)
"Place was clean, safe, parking was easy along side streets. Very spacious and reasonably priced! Will stay again! "
The price is AU$621
includes taxes & fees
25 Aug - 26 Aug
Upscale 4BR Retreat: Wicker Park

Luxury Home Away From Your Home

8.8 out of 10, Excellent, (126)
"Perfect for what we were looking for!"
Luxury Home Away From Your Home
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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