Best Boutique Hotels in South Side

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Boutique Hotels

Next weekend
In two weeks

Our top choices for South Side boutique hotels

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,001 reviews)
"Clean hotel great restaurant "
United States
ELIZABETH
The price is RM604
RM718 total
includes taxes & fees
10 May - 11 May
L7 Chicago by LOTTE

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,056 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is RM528
RM744 total
includes taxes & fees
25 May - 26 May
Staypineapple, An Iconic Hotel, The Loop

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, (1,231 reviews)
"Really nice stay. "
United States
Rachael Lindsay
The price is RM600
RM705 total
includes taxes & fees
25 May - 26 May
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,363 reviews)
"It was in a great location near everything. "
United States
Dwight Demond
The price is RM543
RM645 total
includes taxes & fees
7 May - 8 May
The Chicago Hotel Collection - Magnificent Mile

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,104 reviews)
"Clean rooms and very good location. "
Canada
Rudra
The price is RM435
RM518 total
includes taxes & fees
25 May - 26 May
Central Loop Hotel

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,491 reviews)
"Very well located Staff were amazing"
Canada
Gisele
The price is RM635
RM755 total
includes taxes & fees
10 May - 11 May
Eurostars Magnificent Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,246 reviews)
"Spacious room and great staff"
Canada
Manjeet
The price is RM505
RM593 total
includes taxes & fees
25 May - 26 May
Ivy Boutique Hotel

The Buckingham Hotel

The Buckingham Hotel
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,001 reviews)
"Nice place; good views. "
United States
Jessica
The price is RM476
RM615 total
includes taxes & fees
27 May - 28 May
The Buckingham Hotel

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,569 reviews)
"Clean room, great staff, amazing location. "
United States
Alexa
The price is RM592
RM830 total
includes taxes & fees
25 May - 26 May
The Royal Sonesta Chicago River North

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,393 reviews)
"Very friendly staff, great location."
Canada
Annabel
The price is RM794
RM1,055 total
includes taxes & fees
10 May - 11 May
Sports Illustrated Resorts Chicago
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

Explore a world of travel with Expedia