Find Boutique Hotels in South Side, IL

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on South Side Boutique Hotels

Tonight
Aug 3 - Aug 4
Tomorrow
Aug 4 - Aug 5
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top South Side Boutique Hotels

The Wheeler Mansion
Classic hotel room with a large bed, bedside lamps, and ornate mirror.

The Wheeler Mansion

4.0 star property
10.0 out of 10, Exceptional, (1)
"A unique place to stay near the convention centre. "
The price is ₩748,850
₩905,287 total
includes taxes & fees
Aug 12 - Aug 13
The Wheeler Mansion
Ivy Boutique Hotel
Stunning city views from a sleek, high-rise building with a dynamic design and lush greenery.

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1009)
"Great location and hotel "
The price is ₩205,266
₩240,962 total
includes taxes & fees
Sep 2 - Sep 3
Ivy Boutique Hotel
The Chicago Hotel Collection - Magnificent Mile
Relax in a serene urban setting with a spacious seating area and unobstructed city views.

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1135)
"Enjoyed staying here!"
The price is ₩46,269
₩249,952 total
includes taxes & fees
Aug 4 - Aug 5
The Chicago Hotel Collection - Magnificent Mile
L7 Chicago by LOTTE
Stunning hotel exterior with a sleek glass canopy and modern design.

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2766)
"Great place to stay "
The price is ₩319,634
₩375,218 total
includes taxes & fees
Aug 17 - Aug 18
L7 Chicago by LOTTE
The Whitehall Hotel, BW Premier Collection
Relax in a spacious room with a large bed, a smaller bed, and a comfortable seating area.

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very Good, (3521)
"We had a great stay! "
The price is ₩166,109
₩194,996 total
includes taxes & fees
Sep 2 - Sep 3
The Whitehall Hotel, BW Premier Collection
Virgin Hotels Chicago
Relax on the rooftop with a mix of seating options and potted plants, overlooking a historic building and modern skyscrapers.

Virgin Hotels Chicago

4.5 star property
9.2 out of 10, Wonderful, (1338)
"Great area and very walkable to local attractions "
The price is ₩307,612
₩401,889 total
includes taxes & fees
Sep 1 - Sep 2
Virgin Hotels Chicago
Trump International Hotel & Tower Chicago
Enjoy breathtaking views of the city skyline from the expansive window.

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1671)
"Great hotel "
The price is ₩651,314
₩764,577 total
includes taxes & fees
Aug 18 - Aug 19
Trump International Hotel & Tower Chicago
ACME Hotel Company
Enjoy a casual drink at the bar, where a variety of beverages are available.

ACME Hotel Company

3.5 star property
9.0 out of 10, Wonderful, (1734)
"Lovely stay! Staff was excellent!!!"
The price is ₩198,833
₩233,417 total
includes taxes & fees
Aug 11 - Aug 12
ACME Hotel Company
The Talbott, Autograph Collection
Experience the classic charm of the Talbott Hotel, featuring an ornate entrance and large windows.

The Talbott, Autograph Collection

4.5 star property
9.2 out of 10, Wonderful, (26)
"Fantastic location and hotel! "
The price is ₩280,673
₩364,218 total
includes taxes & fees
Aug 24 - Aug 25
The Talbott, Autograph Collection
Staypineapple, An Iconic Hotel, The Loop
Stunning interior space with ornate iron gates, marble panels, and a patterned rug.

Staypineapple, An Iconic Hotel, The Loop

4.0 star property
9.4 out of 10, Exceptional, (1005)
"I always recommend this hotel to my guests and book travel for other people here. Super friendly awesome staff, great place to stay downtown and very convenient location. "
The price is ₩294,081
₩385,920 total
includes taxes & fees
Aug 24 - Aug 25
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.

Top South Side Hotel Reviews

Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Easy access to Chinatown and short walk to the Red Line. Comfortable room, very clean and modern."
Kevin 2-night trip
Posted 3 days ago
Jaslin Hotel