Southwest Side Holiday Rentals

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Check prices for these dates

Holiday Rentals in Southwest Side

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (680)
"This is a great hotel. The rooms have a kitchenette and the staff is wonderful! Beautiful hotel, great amenities. "
The price is AU$249
includes taxes & fees
25 Feb - 26 Feb
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (432)
"Even though this is a busy area, it was quiet. a lot of restaurants within walking distance."
The price is AU$180
includes taxes & fees
23 Mar - 24 Mar
Sonder South Wabash

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is AU$223
includes taxes & fees
13 Mar - 14 Mar
Found Chicago powered by Sonder

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (257)
"It was wonderful!"
The price is AU$209
includes taxes & fees
12 Mar - 13 Mar
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 AU$232
includes taxes & fees
11 Mar - 12 Mar
Sonder The Burnham Apartments

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (363)
"Great location, comfortable, would have opted for a traditional hotel with routine service had I known it was not offered."
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (288)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is AU$317
includes taxes & fees
24 Feb - 25 Feb
Level Chicago – Old Town

Comfort Inn Chicago Wind Creek Casino

2.5 star property
4.8 out of 10, (3)
"I was told on arrival that my room was given to somebody else I wasn’t notified or nothing and I’m still waiting on a refund"
The price is AU$159
includes taxes & fees
21 Feb - 22 Feb
Comfort Inn Chicago Wind Creek Casino

The Neighborhood Hotel-Little Italy

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

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (258)
"Best place to stay in Chicago. "
Kasa South Loop Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (138)
"Loved it Had to leave early but loved "
The price is AU$190
includes taxes & fees
12 Mar - 13 Mar
Sonder Jewelers Row

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (125)
"The property is very nice, we will definitely coming back soon "
The price is AU$173
includes taxes & fees
27 Feb - 28 Feb
Kasa River North Chicago

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is AU$179
includes taxes & fees
12 Mar - 13 Mar
Sonder The Opal

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (90)
"Great apartment, we were given an extra bedroom which we used as a wardrobe. Well equipped, modern and well decorated. Full cooker, fridge freezer, microwave. We were provided with tablets for laundry and dishwasher. Washing up.liquids, towels and toilet roll. Great shower. Loved the location. We enjoy cities and walking. Trains a very short walks (several L stations). Target was a 15 minute walk, great independent coffee shop 2 mins from entrance. We will use Sonder again. "
The price is AU$212
includes taxes & fees
23 Feb - 24 Feb
Sonder The Plymouth

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 AU$233
includes taxes & fees
20 Mar - 21 Mar
Sonder Greektown

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is AU$224
includes taxes & fees
21 Feb - 22 Feb
Wrigleyville Suites

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (72)
"Great property, perfect for two people. Easy walk to Wrigley. Stayed there on a couple cold winter days, and being a basement unit, the heater couldn’t keep up very well, so it was a little colder than ideal, but nothing a sweatshirt or extra blanket couldn’t fix. Would definitely go back!"
Wrigley/Southport Corridor Garden Oasis +parking!

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (23)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

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

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
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 Southwest Side you may be interested in

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3800)
"I like the hotel at downtown area, it’s convenient for everything."
The price is AU$167
includes taxes & fees
5 Mar - 6 Mar
River Hotel

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8525)
"A comfortable historical hotel, enjoyed the bar area, cocktails were good , would not recommend dining at the hotel. On Expedia it says it has parking and in and out privileges but this is not true, once you park you cant leave unless paying again (62$) . Had a paranormal experience in room 917 so don't be surprised if you see ghosts at night "
The price is AU$158
includes taxes & fees
23 Feb - 24 Feb
Congress Plaza Hotel

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1662)
"I had a great stay over Valentine’s Day weekend. The staff was friendly and it was near everything. "
The price is AU$238
includes taxes & fees
23 Feb - 24 Feb
L7 Chicago by LOTTE
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.