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Far Southwest Side Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Far Southwest Side holiday rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,273 reviews)
"Nice stay"
United States
Heather
The price is HK$1,186
HK$1,622 total
includes taxes & fees
7 Sept - 8 Sept
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (15 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,412
HK$2,145 total
includes taxes & fees
20 Aug - 21 Aug
Kasa Lake Shore Chicago
Full-sized fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (518 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is HK$1,866
HK$2,385 total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
TV, offices

4. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,687
HK$2,280 total
includes taxes & fees
23 Aug - 24 Aug
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

5. Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.2 out of 10, Wonderful, (7 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is HK$2,643
HK$6,496 total
includes taxes & fees
13 Sept - 14 Sept
Modern West Loop Gem-City Views & Prime Location 5
Exterior

6. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
The price is HK$4,722
HK$8,635 total
includes taxes & fees
27 Aug - 28 Aug
Envitae Hotel, 4BR Modern Sleek Apartment
Interior

7. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
The price is HK$1,012
HK$3,059 total
includes taxes & fees
20 Aug - 21 Aug
Plymouth Collection: 3BD 2BA High Floor with Gym
Coffee/tea maker, fridge, microwave, oven

8. Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (7 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is HK$2,745
HK$5,721 total
includes taxes & fees
25 Aug - 26 Aug
Downtown Chicago Stay with Free In & Out Parking 4
1 bedroom, iron/ironing board, travel cot, WiFi

9. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is HK$1,631
HK$2,196 total
includes taxes & fees
20 Aug - 21 Aug
LIVN West Loop Chicago King Studio
Interior

10. South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is HK$2,620
HK$5,537 total
includes taxes & fees
13 Sept - 14 Sept
South Loop Rooftop With In and Out Parking 3
TV, offices

11. LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
The price is HK$1,443
HK$1,946 total
includes taxes & fees
23 Aug - 24 Aug
LIVN Millennium Park Downtown Chicago Superior 1BR
Dining

12. LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is HK$1,592
HK$2,150 total
includes taxes & fees
23 Aug - 24 Aug
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

13. Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.6 out of 10, Exceptional, (11 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
Modern West Loop Gem-City Views & Prime Location 2
Interior

14. Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
9.6 out of 10, Exceptional, (8 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is HK$1,600
HK$5,024 total
includes taxes & fees
30 Aug - 31 Aug
Modern West Loop Gem-City Views & Prime Location 3
Interior

15. River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.0 out of 10, Wonderful, (9 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
The price is HK$1,459
HK$3,901 total
includes taxes & fees
8 Sept - 9 Sept
River North Rooftop With In and Out Parking 3
Dining

16. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$1,239
HK$1,648 total
includes taxes & fees
20 Aug - 21 Aug
LIVN Millennium Park Downtown Chicago Studio
Lounge

17. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is HK$1,747
HK$2,871 total
includes taxes & fees
25 Aug - 26 Aug
At Home in Oak Park
Property grounds

18. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (31 reviews)
"I had a fun stay "
United States
Jusu K.
The price is HK$1,122
HK$1,591 total
includes taxes & fees
30 Aug - 31 Aug
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Coffee/tea maker, fridge, microwave, oven

19. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (78 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is HK$1,073
HK$2,638 total
includes taxes & fees
24 Aug - 25 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!
Dining

20. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (31 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is HK$539
HK$1,424 total
includes taxes & fees
23 Aug - 24 Aug
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
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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Top Far Southwest Side Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Fantastic location. Staff was friendly, efficient & helpful. Nice room. Hotel is near lots of restaurants & shops. Really enjoyed our stay."
Debra 4-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

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