Photo by Richard Remington
Search Romantic Hotels in South Side
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on South Side Romantic Hotels
Top South Side Romantic Hotels
Sophy Hyde Park
Hyde Park
9.6 out of 10, Exceptional, (1000)
"Room and location were great"
Latasha
The price is 5.435.063 ₫
7.092.502 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Swissotel - Chicago
Downtown Chicago
9.0 out of 10, Wonderful, (2989)
"Great stay"
Lorrington Ashford
The price is 2.495.018 ₫
3.702.949 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Palmer House a Hilton Hotel
Downtown Chicago
8.4 out of 10, Very good, (2116)
"Loved and enjoyed our stay"
Luis
The price is 2.703.028 ₫
3.832.360 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4 out of 10, Exceptional, (2254)
"Perfect environment and location"
YIWEI
The price is 2.443.722 ₫
3.766.687 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Aloft Chicago Mag Mile
Downtown Chicago
8.6 out of 10, Excellent, (2944)
"Great location and great staff!!"
lynne
The price is 2.373.390 ₫
2.786.121 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
9.2 out of 10, Wonderful, (2098)
"Would stay again. "
Montroy
The price is 2.602.619 ₫
3.860.118 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Hyatt Regency Chicago
Downtown Chicago
9.4 out of 10, Exceptional, (3379)
"Nice hotel"
Dick
The price is 3.586.456 ₫
4.984.131 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Royal Sonesta Chicago Downtown
Downtown Chicago
9.4 out of 10, Exceptional, (3105)
"Very nice staff, beautiful hotel and a clean room"
Tara
The price is 3.006.294 ₫
4.372.962 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
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
Explore a world of travel with Expedia
Choose Your South Side Hotel Style
- Beach Resorts & 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-Friendly Hotels in South Side
- Golf Hotels in South Side
- Historic Hotels in South Side
- Hotels near Museums in South Side
- Hotels with Air Conditioning in South Side
- Hotels with Balcony in South Side
- Hotels with Breakfast in South Side
- Hotels with Connecting Rooms in South Side
- Hotels with Early Check-in in South Side
- Hotels with Entertainment in South Side
- Hotels with Gym in South Side
- Hotels with Hot Tubs in South Side
- Hotels with Laundry Service in South Side
- Hotels with Parking in South Side
- Hotels with Parking in South Side
- Hotels with Pool in South Side
- Hotels with Restaurant in South Side
- Hotels with Room Service in South Side
- Hotels with Wifi in South Side
- Hotels with a Bar in South Side
- Hotels with a View in South Side
- Lakeside Hotels in South Side
- Luxury Hotels in South Side
- Shopping Hotels in South Side
- Spa Hotels in South Side
- Sports Hotels in South Side
- Wedding Hotels in South Side