Find Boutique Hotels in Near South Side, IL

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Check availability on Near South Side Boutique Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Near South Side Boutique Hotels

Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3140)
"Amazing and will be staying again!"
United States
Angie
The price is AED 344
AED 404 total
includes taxes & fees
5 Jan - 6 January 2026
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

3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (3785)
"Great location "
United States
Carlos
The price is AED 281
AED 330 total
includes taxes & fees
8 Dec - 9 Dec
The Whitehall Hotel, BW Premier Collection
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3340)
"I loved the location."
United States
Laura
The price is AED 518
AED 608 total
includes taxes & fees
1 Jan - 2 January 2026
L7 Chicago by LOTTE
Terrace/patio
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2301)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is AED 378
AED 562 total
includes taxes & fees
4 Jan - 5 January 2026
The Royal Sonesta Chicago River North
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, (1107)
"Great hotel for price and location Everything clean and a huge room "
United States
James
The price is AED 350
AED 410 total
includes taxes & fees
4 Jan - 5 January 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1923)
"Very clean and well maintained room, comfortable bed, and great location!"
United States
Rebecca
The price is AED 305
AED 359 total
includes taxes & fees
11 Dec - 12 Dec
Central Loop Hotel
Lobby sitting area
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, (2424)
"This hotel was perfect, all the ameneties need for a weekend on Chicago"
United States
Nicole
Hotel Felix River North/Magnificent Mile
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1032)
"Clean room, nice amenities (especially like the rain shower), very centrally located, and friendly staff. "
United States
Kathleen
The price is AED 374
AED 439 total
includes taxes & fees
4 Jan - 5 January 2026
Ivy Boutique Hotel
Rooftop terrace
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1417)
"Excellent hotel the rooms are awesome "
United States
Devita
The price is AED 657
AED 897 total
includes taxes & fees
8 Dec - 9 Dec
Virgin Hotels 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, (1003)
"Perfect stay. Great location, lovely room with view of Marshall Fields State Street Christmas display. The people were just great."
United States
James
The price is AED 388
AED 563 total
includes taxes & fees
22 Dec - 23 Dec
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 Near South Side Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Thank to Mr.Robert for getting a good room with a beautiful view of the river "
Armando 4-night trip
Posted 15 hours ago
The Royal Sonesta Chicago Downtown

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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.