Find Boutique Hotels in Near South Side, IL

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Check availability on Near South Side Boutique Hotels

Tonight
Dec 23 - Dec 24
Tomorrow
Dec 24 - Dec 25
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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
Bar (on property)
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, (3785)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is NT$2,414
NT$2,834 total
includes taxes & fees
Jan 5 - 2026/1/6
The Whitehall Hotel, BW Premier Collection
55-inch LCD TV with cable channels, TV, pay movies
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3427)
"Very good stay "
United States
david
The price is NT$4,372
NT$5,132 total
includes taxes & fees
Dec 28 - Dec 29
L7 Chicago by LOTTE
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3156)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is NT$2,952
NT$3,466 total
includes taxes & fees
Jan 22 - 2026/1/23
Eurostars Magnificent Mile
Lobby
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, (2468)
"Decent hotel in a great location with extremely helpful staff. "
United States
Aaron
Hotel Felix River North/Magnificent Mile
Nightclub
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1949)
"Good value and location worked well for our trip"
United States
Todd
The price is NT$2,358
NT$2,768 total
includes taxes & fees
Dec 25 - Dec 26
Central Loop Hotel
Bar (on property)
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1051)
"I love this hotel "
United States
Tiara
The price is NT$2,444
NT$2,869 total
includes taxes & fees
Jan 14 - 2026/1/15
Ivy Boutique Hotel
Breakfast, lunch, dinner served; American cuisine
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, (2329)
"The room was beautiful ❤️❤️ I enjoyed the hot tub and the views !! "
United States
Mary
The price is NT$3,497
NT$5,114 total
includes taxes & fees
Jan 4 - 2026/1/5
The Royal Sonesta Chicago River North
Dinner served, American cuisine
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, (1009)
"Great hotel location and friendly staff! "
United States
Kathleen
The price is NT$3,375
NT$4,886 total
includes taxes & fees
Jan 8 - 2026/1/9
Staypineapple, An Iconic Hotel, The Loop
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, (1125)
"Amazing hotel "
United States
Alondra
The price is NT$3,003
NT$3,525 total
includes taxes & fees
Jan 12 - 2026/1/13
Bluegreen Vacations Hotel Blake, an Ascend Collection 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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Room is comfortable and clean. It is nice to stay at a historical site "
Lisa 1-night trip
Posted 4 hours ago
Palmer House a Hilton Hotel

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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