Boutique Hotels in South Side, Chicago

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Our top choices for South Side boutique hotels

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,875 reviews)
"Great property, staff was amazing"
United States
Mamta Singh
The price is P27,548
P32,751 total
includes taxes & fees
May 26 - May 27
Trump International Hotel & Tower Chicago

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,058 reviews)
"Clean hotel great restaurant "
United States
ELIZABETH
The price is P15,221
P18,096 total
includes taxes & fees
May 26 - May 27
L7 Chicago by LOTTE

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (3,960 reviews)
"Nice location , good service, and tastier breakfast"
Mexico
Rogelio
The price is P8,345
P9,921 total
includes taxes & fees
May 26 - May 27
The Whitehall Hotel, BW Premier Collection

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,405 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is P12,326
P16,393 total
includes taxes & fees
May 27 - May 28
Sports Illustrated Resorts Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,001 reviews)
"Wonderful Hotel will definitely be looking forward to going back."
United States
Shante
The price is P31,746
P37,742 total
includes taxes & fees
May 25 - May 26
Waldorf Astoria Chicago

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, (1,235 reviews)
"Really nice stay. "
United States
Rachael Lindsay
The price is P9,815
P11,670 total
includes taxes & fees
May 25 - May 26
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,072 reviews)
"Clean rooms, comfy bed."
United States
Brenda
The price is P9,815
P13,501 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,264 reviews)
"Great stay! "
United States
Taira
The price is P8,170
P9,591 total
includes taxes & fees
May 26 - May 27
Ivy Boutique Hotel

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,035 reviews)
"It was comfortable and in a fun area with lots to do"
United States
Ashley
The price is P8,555
P10,171 total
includes taxes & fees
May 25 - May 26
ACME Hotel Chicago, Outset Collection by Hilton

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,555 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is P9,877
P11,743 total
includes taxes & fees
May 25 - May 26
Eurostars Magnificent Mile
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