Photo by Richard Remington
Romantic Hotels & Resorts in South Side from NZ$163
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on South Side Romantic Hotels
Our top choices for South Side romantic hotels
9.6 out of 10, Exceptional, (1001)
"Great staff, location and ambience."
Jaison
The price is NZ$383
includes taxes & fees
14 Dec - 15 Dec
8.6 out of 10, Excellent, (2952)
"Great location and great staff!!"
lynne
The price is NZ$163
includes taxes & fees
4 Jan - 5 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonDowntown Chicago
9.4 out of 10, Exceptional, (2258)
"This place was amazing !"
Jayla Danyell
The price is NZ$252
includes taxes & fees
23 Dec - 24 Dec
9.4 out of 10, Exceptional, (3388)
"I always love staying at this place when I visit"
William
The price is NZ$325
includes taxes & fees
28 Dec - 29 Dec
8.4 out of 10, Very good, (2125)
"Loved and enjoyed our stay"
Luis
The price is NZ$267
includes taxes & fees
21 Dec - 22 Dec
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileDowntown Chicago
8.2 out of 10, Very good, (2741)
"Great food clean room friendly staff"
MARINA
The price is NZ$198
includes taxes & fees
23 Dec - 24 Dec
9.0 out of 10, Wonderful, (3145)
"Great location "
Christian
The price is NZ$174
includes taxes & fees
11 Jan - 12 Jan 2026
9.2 out of 10, Wonderful, (2115)
"Great hotel. Very affordable for such a perfect location."
Nicholas
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.
Top South Side Hotel Reviews
Chinatown Hotel Chicago
10/10 Excellent
Hyatt Place Chicago-South/University Medical Center
10/10 Excellent
Explore a world of travel with Expedia
Places Near South Side
What kind of hotels are in South Side?
- Adults Only in South Side
- Adventure Sport Hotels in South Side
- Beach Hotels in South Side
- Boutique Hotels in South Side
- Business Hotels in South Side
- Casino Hotels in South Side
- Cheap Hotels in South Side
- Family Hotels in South Side
- Golf Hotels in South Side
- Green Hotels in South Side
- Historic Hotels in South Side
- Hotels with Parking in South Side
- Hotels with Pool in South Side
- LGBT Welcoming Hotels in South Side
- Luxury Hotels in South Side
- Pet Friendly Hotels in South Side
- Spa Hotels in South Side
More accommodation types in South Side
Hotels near popular Chicago Attractions
Explore more hotels
- Admiral Motel By Oyo Chicago I-94
- Chicago Lake Shore Hotel
- Rainbow Motel
- Stylish Apartment near Chicago Downtown
- Best Motel By OYO Chicago I-90
- LakeHouse
- A Home Away From Home!
- South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
- House with garage, outdoor dining and basement bar
- Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
- Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
- Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
- Stay, Relax & Explore Chicago
- Modern Studio Near UChicago
- Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
More ways to book
Expedia's Latest Trends
Hotels
- Hotels near Te Pae Christchurch Convention and Exhibition Centre
- Cheap Hotels in Milan
- Christchurch accommodation
- Hotels near Lollapalooza
- Cheap Hotels in Chicago
- La Quinta by Wyndham Remarkables Park Queenstown
- Pyes Pa accommodation
- Moxy NYC Times Square
- Marshall Islands accommodation
- Fitzherbert Regency Motor Lodge
- Quest Taupo Serviced Apartments
- Clyde accommodation
- Frankton Accommodation
- Rendezvous Surf Camp Fiji - Hostel
- Motels Waihola
Flights
General