Find Boutique Hotels in Near South Side, IL

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Check availability on Near South Side Boutique Hotels

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Near South Side boutique hotels

Signature Suite, 1 Bedroom | Premium bedding, pillowtop beds, individually decorated
The Wheeler Mansion

The Wheeler Mansion

The Wheeler Mansion
4.0 star property
Near South Side
9.0 out of 10, Wonderful, (4)
"A unique place to stay near the convention centre. "
United States
Leonardo
The Wheeler Mansion
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3170)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is NT$2,942
NT$3,454 total
includes taxes & fees
Jan 26 - 2026/1/27
Eurostars Magnificent Mile
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection

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, (3815)
"Hotel stay was excellent, great dining options walkable, easy parking "
United States
Jason
The price is NT$2,406
NT$2,825 total
includes taxes & fees
Jan 5 - 2026/1/6
The Whitehall Hotel, BW Premier Collection
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3447)
"Amazing place to stay and super accommodating "
United States
Carson
The price is NT$4,357
NT$5,114 total
includes taxes & fees
Dec 30 - Dec 31
L7 Chicago by LOTTE
Interior detail
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1012)
"Location was great, staff was very friendly, and the rooms were clean. "
United States
Lori
The price is NT$3,363
NT$4,869 total
includes taxes & fees
Jan 14 - 2026/1/15
Staypineapple, An Iconic Hotel, The Loop
Lobby sitting area
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2482)
"Decent hotel in a great location with extremely helpful staff. "
United States
Aaron
The price is NT$2,791
NT$4,236 total
includes taxes & fees
Jan 2 - 2026/1/3
Hotel Felix River North/Magnificent Mile
Terrace/patio
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2339)
"Great property and room"
United States
Steven
The price is NT$3,485
NT$5,097 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

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1130)
"Amazing hotel "
United States
Alondra
The price is NT$2,993
NT$3,513 total
includes taxes & fees
Jan 18 - 2026/1/19
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1956)
"Good value and location worked well for our trip"
United States
Todd
The price is NT$2,614
NT$3,069 total
includes taxes & fees
Dec 29 - Dec 30
Central Loop Hotel
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1049)
"I love this hotel "
United States
Tiara
Ivy Boutique Hotel
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 Near South Side Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Easy check in and check out, staff were very friendly, room was great, bed was very comfortable. The hotel was also very clean. We loved the location. It was so close to Michigan Avenue, but it was quiet. "
Cindy 1-night trip
Posted 3 hours ago
Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

What's the best boutique accommodation in Near South Side?
The Wheeler Mansion is a favorite hotel with our travelers looking for a stylish accommodation, and features 10 guestrooms, free breakfast, and free parking.
What's there to see and do in Near South Side?
The scenery, lakefront, and restaurants are just some of the things to enjoy while you're in the area. Top activities and sights around Near South Side include Michigan Avenue, Wrigley Field, and Soldier Field. You might also want to see places like Navy Pier, United Center, and Arie Crown Theater during your trip.
What's the best way to get to my boutique hotel in Near South Side?
You have a few options for transportation to and around Near South Side. The closest major airport is Chicago Midway Airport (MDW), which is located 7.9 mi (12.7 km) away, but Chicago O'Hare Intl. Airport (ORD) may also be an option. Local metro stations include Cermak-McCormick Place Station and Roosevelt Station.

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