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Far Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Far Southwest Side vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,296 reviews)
"A great place"
United States
Lahiru
The price is ￥24,312
￥33,228 total
includes taxes & fees
Sep 8 - Sep 9
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 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 ￥40,447
￥51,423 total
includes taxes & fees
Sep 7 - Sep 8
Level Chicago – Old Town

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (25 reviews)
"Great location and super clean!"
United States
Erica
The price is ￥29,299
￥44,333 total
includes taxes & fees
Sep 9 - Sep 10
Kasa Lake Shore Chicago
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

4. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ￥31,958
￥43,238 total
includes taxes & fees
Sep 7 - Sep 8
LIVN Millennium Park Downtown Chicago 2BR
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

5. 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 ￥28,443
￥38,518 total
includes taxes & fees
Sep 7 - Sep 8
LIVN West Loop Chicago King Studio

6. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.6 out of 10, Exceptional, (4 reviews)
"Really enjoyed staying at this property! Clean and safe. Would recommend!"
United States
Emmeline R.
The price is ￥106,740
￥190,873 total
includes taxes & fees
Sep 18 - Sep 19
Modern 3BR Apartment Near North Ave Shops

7. Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.6 out of 10, Exceptional, (13 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is ￥23,489
￥89,541 total
includes taxes & fees
Sep 7 - Sep 8
Modern West Loop Gem-City Views & Prime Location 4

8. 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 ￥54,808
￥114,969 total
includes taxes & fees
Sep 13 - Sep 14
South Loop Rooftop With In and Out Parking 3

9. Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (10 reviews)
"Perfect place for my family’s visit to Chicago."
United States
Jason L.
The price is ￥47,937
￥105,113 total
includes taxes & fees
Sep 16 - Sep 17
Downtown Chicago Stay with Free In & Out Parking 3
A modern kitchen with a central island, bar stools, and a dining table.

10. River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (13 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is ￥47,298
￥108,514 total
includes taxes & fees
Sep 29 - Sep 30
River North Private Deck With In and Out Parking
A kitchen with white cabinets, a microwave, a kettle, and a toaster.

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

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 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 ￥25,726
￥69,679 total
includes taxes & fees
Sep 8 - Sep 9
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

12. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is ￥21,891
￥59,068 total
includes taxes & fees
Sep 7 - Sep 8
River North Private Balcony With In and Out Parking
A spacious living room with a large sectional sofa, a glass coffee table, and a wooden staircase.

13. Scott C.H. - Chicago Getaway

Scott C.H. - Chicago Getaway
Near North Side
The price is ￥144,047
￥198,344 total
includes taxes & fees
Sep 7 - Sep 8
Scott C.H. - Chicago Getaway
A room with a large window, a round table with chairs, a television, and a lamp.

14. 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 ￥29,401
￥39,843 total
includes taxes & fees
Sep 7 - Sep 8
LIVN Millennium Park Downtown Chicago Superior 1BR
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

15. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is ￥29,401
￥39,843 total
includes taxes & fees
Sep 7 - Sep 8
LIVN West Loop Chicago Queen Superior Studio
A wooden deck with a railing, a staircase, and a window with a wreath.

16. 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, (34 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥22,866
￥33,486 total
includes taxes & fees
Sep 7 - Sep 8
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern kitchen with wooden cabinets, a microwave, and a stove. There is a purple sofa and a small table with chairs. A suitcase is on the floor next to the sofa.

17. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
The price is ￥28,131
￥43,837 total
includes taxes & fees
Sep 10 - Sep 11
Chicago Second Floor Studio by 747 Lofts

18. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
10.0 out of 10, Exceptional, (4 reviews)
"Exactly as described, would recommend"
United States
Anonymous traveler
The price is ￥29,561
￥84,586 total
includes taxes & fees
Sep 7 - Sep 8
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A brick building with a sign for 'Irish Declans' Pub' and outdoor seating with metal chairs and tables.

19. Scott C.H.

Scott C.H.
2.0 star property
Near North Side
The price is ￥121,282
￥206,150 total
includes taxes & fees
Sep 8 - Sep 9
Scott C.H.
A living room with a blue sectional sofa, a glass coffee table, and yellow curtains.

20. Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.2 out of 10, Wonderful, (11 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
The price is ￥18,839
￥42,547 total
includes taxes & fees
Sep 8 - Sep 9
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Amazing hotel ! Was in the midst of everything and the staff was extremely helpful and even upgraded our room! Would definitely book again"
Dwayne 2-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown

Find out more about Far Southwest Side

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