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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Southwest Side apartments

Smart TV, video games

1. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Game room

2. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is AED 242
AED 962 total
includes taxes & fees
29 Sep - 30 Sep
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
2 bedrooms, desk, iron/ironing board, WiFi

3. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
Spacious Apt | 4 Queen Beds | Free Parking
Interior

4. South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is AED 404
AED 1,428 total
includes taxes & fees
21 Sep - 22 Sep
South Loop Rooftop With In and Out Parking 2
1 bedroom, iron/ironing board, travel crib, WiFi

5. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (23 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is AED 676
AED 902 total
includes taxes & fees
20 Sep - 21 Sep
LIVN West Loop Chicago Queen Superior Studio
TV

6. Modern 1BR in Prime West Loop Location

Modern 1BR in Prime West Loop Location
Downtown Chicago
The price is AED 812
AED 1,614 total
includes taxes & fees
19 Oct - 20 Oct
Modern 1BR in Prime West Loop Location
TV, offices

7. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is AED 771
AED 1,037 total
includes taxes & fees
21 Sep - 22 Sep
LIVN Millennium Park Downtown Chicago 1 BR
TV, offices

8. 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 AED 871
AED 1,852 total
includes taxes & fees
20 Sep - 21 Sep
River North Private Balcony With In and Out Parking
TV

9. Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is AED 617
AED 1,198 total
includes taxes & fees
29 Sep - 30 Sep
Stylish Japanese-Themed 2BR Apt Close to Downtown
Coffee/tea maker, fridge, microwave, oven

10. Wabash 4BR - Pool, Free In & Out Parking 4

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
The price is AED 962
AED 2,652 total
includes taxes & fees
29 Sep - 30 Sep
Wabash 4BR - Pool, Free In & Out Parking 4
Coffee/tea maker, fridge, microwave, oven

11. 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, (15 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
River North Private Deck With In and Out Parking
Interior

12. Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6
Downtown Chicago
The price is AED 1,469
AED 2,901 total
includes taxes & fees
1 Oct - 2 Oct
Downtown Chicago Stay with Free In & Out Parking 6
Dining

13. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
The price is AED 259
AED 804 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Urban View Retreat Near Downtown - Sleeps 7
1 bedroom, iron/ironing board, travel crib, WiFi

14. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is AED 962
AED 1,293 total
includes taxes & fees
24 Sep - 25 Sep
LIVN West Loop Chicago Classic Queen Studio
1 bedroom, iron/ironing board, travel crib, WiFi

15. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is AED 1,131
AED 1,523 total
includes taxes & fees
24 Sep - 25 Sep
LIVN West Loop Chicago King Studio
Dining

16. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is AED 786
AED 1,050 total
includes taxes & fees
20 Sep - 21 Sep
LIVN Millennium Park Downtown Chicago Studio
TV, offices

17. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great property"
United States
duane
The price is AED 1,028
AED 1,371 total
includes taxes & fees
20 Sep - 21 Sep
LIVN West Loop Chicago 2 BR City View
Interior

18. 2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
9.6 out of 10, Exceptional, (4 reviews)
"Great host very accommodating."
United States
Kali P.
The price is AED 338
AED 1,283 total
includes taxes & fees
27 Sep - 28 Sep
2MI to Obama Center - Pet-Friendly near UOC!
Dining

19. 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 AED 863
AED 1,149 total
includes taxes & fees
20 Sep - 21 Sep
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

20. Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
The price is AED 617
AED 1,134 total
includes taxes & fees
5 Oct - 6 Oct
Chicago-Themed 1BR in a Central Spot near 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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Top Southwest Side Hotel Reviews

River Hotel

River Hotel

8/10 Good
"The room was very small. The gal at check in was kinda rude. Everything seemed a little dated too. But the bed was comfy and the shower was hot. The gentleman at check out literally went out of his way to talk to us. The location was convenient!"
Alyssa 2-night trip
Posted 1 hour ago
River Hotel

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