Find Romantic Hotels in South Side, IL

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on South Side Romantic Hotels

Top South Side Romantic Hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2142)
"Great place to stay!"
The price is ₩283,941
₩373,319 total
includes taxes & fees
Sep 21 - Sep 22
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very Good, (1126)
"Staff was great and loved the breakfast and location!"
The price is ₩199,189
₩233,829 total
includes taxes & fees
Sep 22 - Sep 23
The Chicago Hotel Collection Ambassador Gold Coast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (184)
"Wonderful staff, beautiful hotel and great breakfast!"
The price is ₩307,013
₩346,589 total
includes taxes & fees
Oct 6 - Oct 7
The Publishing House B&B
Wind Creek Southland Casino and Hotel
Couples treatment rooms, sauna, body treatments, aromatherapy

Wind Creek Southland Casino and Hotel

4.0 star property
9.2 out of 10, Wonderful, (111)
"Great place and staff "
The price is ₩274,479
₩307,361 total
includes taxes & fees
Sep 18 - Sep 19
Wind Creek Southland Casino and Hotel
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1957)
"Good place to stay"
The price is ₩198,618
₩265,545 total
includes taxes & fees
Sep 21 - Sep 22
Millennium Knickerbocker Chicago
The Emily Hotel
Exterior

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1222)
"Loved it will be staying here again "
The price is ₩298,784
₩350,742 total
includes taxes & fees
Oct 5 - Oct 6
The Emily Hotel
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (480)
"Everything was taken care of! A wonderful stay. "
The price is ₩157,032
₩260,175 total
includes taxes & fees
Sep 21 - Sep 22
House 5863 - Chicago Bed and Breakfast
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1011)
"I had a wonderful stay I will definitely be back again."
The price is ₩237,996
₩279,375 total
includes taxes & fees
Sep 22 - Sep 23
Ivy Boutique Hotel
theWit Chicago, a Hilton Hotel
Lobby

theWit Chicago, a Hilton Hotel

4.5 star property
9.0 out of 10, Wonderful, (1005)
"It was a great location and very nice hotel with lots to offer. "
The price is ₩360,795
₩464,018 total
includes taxes & fees
Sep 25 - Sep 26
theWit Chicago, a Hilton Hotel
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1983)
"Great room and close to attractions "
The price is ₩205,859
₩282,120 total
includes taxes & fees
Sep 21 - Sep 22
Silversmith Hotel Chicago Downtown
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

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"Loved it"
Todd 1-night trip
Posted 7 days ago
Hyatt Place Chicago-South/University Medical Center

Explore a world of travel with Expedia

Explore a world of travel with Expedia