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Find Boutique Hotels in South Side, IL

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Check availability on South Side Boutique Hotels

Our top choices for South Side boutique hotels

Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3153)
"Amazing and will be staying again!"
United States
Angie
The price is NT$2,924
NT$3,432 total
includes taxes & fees
Jan 8 - 2026/1/9
Eurostars Magnificent Mile
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3346)
"I loved the location."
United States
Laura
The price is NT$4,395
NT$5,159 total
includes taxes & fees
Jan 1 - 2026/1/2
L7 Chicago by LOTTE
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (3802)
"Spacious room, cute boutique hotel in great location!"
United States
Julie
The price is NT$2,387
NT$2,802 total
includes taxes & fees
Jan 7 - 2026/1/8
The Whitehall Hotel, BW Premier Collection
Terrace/patio
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2308)
"Wonderful customer service, great location! "
United States
Michelle
The price is NT$3,461
NT$5,061 total
includes taxes & fees
Jan 4 - 2026/1/5
The Royal Sonesta Chicago River North
Exterior
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1110)
"Great hotel for price and location Everything clean and a huge room "
United States
James
The price is NT$2,969
NT$3,485 total
includes taxes & fees
Jan 6 - 2026/1/7
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1929)
"Very clean and well maintained room, comfortable bed, and great location!"
United States
Rebecca
The price is NT$2,543
NT$2,985 total
includes taxes & fees
Dec 22 - Dec 23
Central Loop Hotel
Rooftop terrace
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1418)
"Excellent hotel the rooms are awesome "
United States
Devita
The price is NT$5,475
NT$7,489 total
includes taxes & fees
Dec 11 - Dec 12
Virgin Hotels Chicago
Interior detail
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1005)
"Great hotel location and friendly staff! "
United States
Kathleen
The price is NT$3,227
NT$4,702 total
includes taxes & fees
Dec 27 - Dec 28
Staypineapple, An Iconic Hotel, The Loop
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1037)
"Clean room, nice amenities (especially like the rain shower), very centrally located, and friendly staff. "
United States
Kathleen
The price is NT$3,087
NT$3,624 total
includes taxes & fees
Dec 11 - Dec 12
Ivy Boutique Hotel
Cocktail bar
ACME Hotel Company

ACME Hotel Company

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1909)
"Lived up to expectations. Bathroom was really nice. Would stay here again."
United States
Nolan
The price is NT$3,340
NT$3,921 total
includes taxes & fees
Dec 14 - Dec 15
ACME Hotel Company
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 South Side Hotel Reviews

Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Excellent service, clean room, great location"
Stefan 1-night trip
Posted 6 days ago
Jaslin Hotel

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