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Find Romantic Hotels in South Side from S$117

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Check availability on South Side Romantic Hotels

Our top choices for South Side romantic hotels

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Sophy Hyde Park

Sophy Hyde Park

4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (1005)
"Great staff, location and ambience."
United States
Jaison
The price is S$278
includes taxes & fees
21 Dec - 22 Dec
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, (2266)
"Smooth check in and beautiful hotel"
United States
Monique
The price is S$190
includes taxes & fees
6 Jan - 7 Jan, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3001)
"Very beautiful place to stay"
United States
FaithBrenda
The price is S$211
includes taxes & fees
3 Jan - 4 Jan, 2026
Swissotel - Chicago
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2956)
"Great location and great staff!!"
United States
lynne
The price is S$117
includes taxes & fees
24 Dec - 25 Dec
Aloft Chicago Mag Mile
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3453)
"Great place to stay "
United States
RaShawna
The price is S$161
includes taxes & fees
15 Dec - 16 Dec
Hilton Chicago/Magnificent Mile Suites
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2108)
"Great hotel. Very affordable for such a perfect location."
United States
Nicholas
Silversmith Hotel Chicago Downtown
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3395)
"I always love staying at this place when I visit"
Canada
William
The price is S$245
includes taxes & fees
4 Jan - 5 Jan, 2026
Hyatt Regency Chicago
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3009)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is S$160
includes taxes & fees
23 Dec - 24 Dec
Warwick Allerton - Chicago
Meeting facility
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1577)
"Great room size and location "
United States
tilden
The price is S$266
includes taxes & fees
21 Dec - 22 Dec
Sheraton Grand Chicago Riverwalk
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2749)
"Great food clean room friendly staff"
United States
MARINA
The price is S$166
includes taxes & fees
6 Jan - 7 Jan, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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 South Side Hotel Reviews

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"I love the staff, and how they make you feel like a valued customer. Clean, friendly, and accessible facilities in a nice part of town."
Charles 1-night trip
Posted 6 days ago
Hyatt Place Chicago-South/University Medical Center

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