South Side Hotel Guide - Romantic Hotels in South Side, Chicago

    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

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, (1076)
"Great place to stay, would definitely recommend and stay here again "
The price is €163
includes taxes & fees
11 Aug - 12 Aug
The Chicago Hotel Collection Ambassador Gold Coast
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1841)
"Nice place to stay"
The price is €196
includes taxes & fees
22 Aug - 23 Aug
Palmer House a Hilton Hotel
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8939)
"Great place to stay."
The price is €253
includes taxes & fees
7 Sept - 8 Sept
Congress Plaza Hotel
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1934)
"Great stay"
The price is €148
includes taxes & fees
24 Aug - 25 Aug
Millennium Knickerbocker Chicago
Wind Creek Southland Casino and Hotel
Couples treatment room(s), sauna, body treatments, aromatherapy

Wind Creek Southland Casino and Hotel

4.0 star property
9.4 out of 10, Exceptional, (80)
"Nice hotel for the area."
The price is €191
includes taxes & fees
11 Aug - 12 Aug
Wind Creek Southland Casino and Hotel
The Blackstone, Autograph Collection
Meeting facility

The Blackstone, Autograph Collection

4.0 star property
9.0 out of 10, Wonderful, (1002)
"Pleasant with great views and a good restaurant."
The price is €224
includes taxes & fees
1 Sept - 2 Sept
The Blackstone, Autograph Collection
Sheraton Grand Chicago Riverwalk
Meeting facility

Sheraton Grand Chicago Riverwalk

4.0 star property
8.4 out of 10, Very good, (1426)
"Nice location and rooms"
The price is €247
includes taxes & fees
1 Sept - 2 Sept
Sheraton Grand Chicago Riverwalk
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.8 out of 10, Excellent, (1363)
"Staff was so friendly and the rooms were really clean!"
The price is €143
includes taxes & fees
24 Aug - 25 Aug
Crowne Plaza Chicago West Loop by IHG
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2607)
"Great location and hotel!"
The price is €145
includes taxes & fees
24 Aug - 25 Aug
Hilton Chicago/Magnificent Mile Suites
The Royal Sonesta Chicago River North
Terrace/patio

The Royal Sonesta Chicago River North

4.5 star property
9.2 out of 10, Wonderful, (2004)
"Great location awesome staff..."
The price is €224
includes taxes & fees
17 Aug - 18 Aug
The Royal Sonesta Chicago River North
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

Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

10/10 Excellent
"Very clean and well kept"
Pamela 4-night trip
Posted 2 days ago
Best Western Inn & Suites - Midway Airport