Boutique Hotels in South Side, Chicago
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Our top choices for South Side boutique hotels
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier CollectionDowntown Chicago
8.2 out of 10, Very Good, (3815)
"Clean room, good location, friendly staff"
Zacharias
The price is P4,495
P5,277 total
includes taxes & fees
Dec 23 - Dec 24
9.6 out of 10, Exceptional, (3411)
"Enjoyed my stay"
Karen
The price is P6,818
P8,003 total
includes taxes & fees
Dec 24 - Dec 25
9.0 out of 10, Wonderful, (3167)
"Amazing stay very clean and beautiful views "
Deigo
The price is P5,496
P6,452 total
includes taxes & fees
Jan 22 - Jan 23, 2026
9.2 out of 10, Wonderful, (2325)
"The room was beautiful ❤️❤️ I enjoyed the hot tub and the views !! "
Mary
The price is P6,518
P9,531 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection HotelDowntown Chicago
9.6 out of 10, Exceptional, (1127)
"Amazing hotel "
Alondra
The price is P5,590
P6,563 total
includes taxes & fees
Jan 11 - Jan 12, 2026
9.4 out of 10, Exceptional, (1009)
"Great hotel location and friendly staff! "
Kathleen
The price is P6,283
P9,096 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.6 out of 10, Excellent, (1948)
"Good value and location worked well for our trip"
Todd
The price is P4,788
P5,621 total
includes taxes & fees
Jan 3 - Jan 4, 2026
8.8 out of 10, Excellent, (1049)
"I love this hotel "
Tiara
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.
Top South Side Hotel Reviews
Jaslin Hotel
10/10 Excellent