A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Find Luxury Hotels in South Side

  • 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 South Side Luxury Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

Our top choices for South Side luxury hotels

View from room

Sophy Hyde Park

Sophy Hyde Park
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (1,002 reviews)
  • cleanliness
    Luxury meets cultural charm in Hyde Park Chicago, where plush bedding and upscale dining create an elegant retreat near lakefront parks.
The price is S$488
includes taxes & fees
27 Jul - 28 Jul
Sophy Hyde Park
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,555 reviews)
The price is S$351
includes taxes & fees
1 Jul - 2 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,440 reviews)
The price is S$422
includes taxes & fees
1 Jul - 2 Jul
Hyatt Regency Chicago
Room service – dining

The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,867 reviews)
  • cleanliness
    Luxurious lakeside retreat in city centre Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
The price is S$260
includes taxes & fees
1 Jul - 2 Jul
The Wade
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,421 reviews)
The price is S$305
includes taxes & fees
5 Jul - 6 Jul
Swissotel - Chicago
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,497 reviews)
  • cleanliness
    Historic Chicago luxury hotel offers spa, pillowtop beds, and prime location near Millennium Park.
The price is S$383
includes taxes & fees
1 Jul - 2 Jul
Palmer House a Hilton Hotel
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,647 reviews)
The price is S$177
includes taxes & fees
6 Jul - 7 Jul
The Chicago Hotel Collection Ambassador Gold Coast
Lunch and dinner served

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,955 reviews)
  • cleanliness
    Indulgent city retreat offers a seasonal outdoor pool, indoor spa sanctuary, and breathtaking skyline views in city centre Chicago.
The price is S$389
includes taxes & fees
6 Jul - 7 Jul
Radisson Blu Aqua Hotel Chicago
Lobby

JW Marriott Chicago

JW Marriott Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Spa indulgence awaits in city centre Chicago where luxurious treatments and premium dining create memorable moments.
The price is S$414
includes taxes & fees
2 Jul - 3 Jul
JW Marriott Chicago
Lounge

Pendry Chicago

Pendry Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,133 reviews)
  • cleanliness
    Indulge in architectural splendour and upscale amenities at this Art Deco Chicago hotel, where luxury meets city centre convenience.
The price is S$507
includes taxes & fees
6 Jul - 7 Jul
Pendry Chicago
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 South Side Hotel Reviews

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Newly renovated and front desk staff EXCELLENT!!!"
Landon 1-night trip
Posted 1 hour ago
Chicago Lake Shore Hotel

Explore a world of travel with Expedia