Search Boutique Hotels in Near South Side

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Near South Side Boutique Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Near South Side Boutique Hotels

Egyptian cotton sheets, premium bedding, pillow-top 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, (3770)
"Great location "
United States
Carlos
The price is 2.018.663 ₫
2.369.709 ₫ total
includes taxes & fees
7 Dec - 8 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, (3328)
"Great location, comfortable hotel "
Australia
Mark
The price is 3.717.011 ₫
4.363.399 ₫ total
includes taxes & fees
1 Jan - 2 Jan 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, (2295)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is 2.698.570 ₫
4.011.723 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Royal Sonesta Chicago River North
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3133)
"Amazing and will be staying again!"
United States
Angie
The price is 2.278.627 ₫
2.674.883 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Eurostars Magnificent Mile
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, (1104)
"Great location - perfect walking distance to main tourist areas."
United States
Alexa
The price is 2.510.519 ₫
2.947.096 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
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, (1002)
"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 3.299.262 ₫
4.645.468 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Staypineapple, An Iconic Hotel, The Loop
Rooftop terrace
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1422)
"Excellent hotel the rooms are awesome "
United States
Devita
The price is 4.720.409 ₫
6.439.271 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Virgin Hotels Chicago
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1030)
"Clean room, nice amenities (especially like the rain shower), very centrally located, and friendly staff. "
United States
Kathleen
The price is 2.667.629 ₫
3.131.530 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Ivy Boutique 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, (2418)
"This hotel was perfect, all the ameneties need for a weekend on Chicago"
United States
Nicole
Hotel Felix River North/Magnificent Mile
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1921)
"Very clean and well maintained room, comfortable bed, and great location!"
United States
Rebecca
The price is 1.952.826 ₫
2.292.422 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Central Loop 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.
View all properties

Top Near South Side Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

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 getting 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 International Airport (ORD) may also be an option. Nearby metro stations include Cermak-McCormick Place Station and Roosevelt Station.