A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Boutique Hotels in South Side, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Boutique Hotels

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

Our top choices for South Side boutique hotels

Champagne service

The Buckingham Hotel

The Buckingham Hotel
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,006 reviews)
"Staff was very helpful and room was clean and ready upon arrival."
United States
Christopher
The price is P9,100
P11,544 total
includes taxes & fees
Jul 19 - Jul 20
The Buckingham Hotel
Exterior

The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites
3.5 star property
Willowbrook
8.6 out of 10, Excellent, (1,569 reviews)
"Great place to stay and celebrate your birthday with that special someone "
United States
Yolanda
The price is P7,557
P9,545 total
includes taxes & fees
Jul 15 - Jul 16
The Champagne Lodge & Luxury Suites
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,714 reviews)
"Enjoyed our stay"
United States
keary
The price is P11,507
P13,680 total
includes taxes & fees
Jul 19 - Jul 20
The Chicago Hotel Collection - Magnificent Mile
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,709 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is P12,299
P14,623 total
includes taxes & fees
Jul 9 - Jul 10
Eurostars Magnificent Mile
55-inch LCD TV with cable channels, TV, pay movies

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,311 reviews)
"Great location and very friendly staff!"
United Kingdom
Alexander
The price is P12,853
P15,281 total
includes taxes & fees
Jul 9 - Jul 10
L7 Chicago by LOTTE
Bar (on property)

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, (3,940 reviews)
"Great location, comfortable rooms, nice breakfast."
United States
Luis
The price is P10,772
P12,806 total
includes taxes & fees
Jul 27 - Jul 28
The Whitehall Hotel, BW Premier Collection
Exterior detail

Carleton of Oak Park

Carleton of Oak Park
3.0 star property
Oak Park
9.2 out of 10, Wonderful, (1,062 reviews)
"Check in was easy, room was clean, it was quiet and location was convenient."
United States
Barbara
The price is P7,520
P8,346 total
includes taxes & fees
Jul 27 - Jul 28
Carleton of Oak Park
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, (1,273 reviews)
"Comfortable hotel in a good location. Lots of public transportation close."
United States
Dean
The price is P12,388
P14,728 total
includes taxes & fees
Jul 26 - Jul 27
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bathroom

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,430 reviews)
"Everything was great! The resort fee is worth paying for! The rooms were nice and clean! The staff was great and overall it was a great experience with good amenities and in the prefect location! "
United States
Kameron
The price is P14,061
P18,472 total
includes taxes & fees
Jul 27 - Jul 28
Sports Illustrated Resorts 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, (1,132 reviews)
"Beautiful historic building; dog friendly!"
United States
Zoe
The price is P21,462
P27,342 total
includes taxes & fees
Jul 16 - Jul 17
Staypineapple, An Iconic Hotel, The Loop
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.
View all properties

Top South Side Hotel Reviews

Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Excellent hotel to stay in with it being our first trip to Chicago! Clean, helpful staff and felt safe at all times there."
Beth 4-night trip
Posted 9 hours ago
Jaslin Hotel