South Side Hotel Guide - Hotels with Connecting Rooms in South Side, Chicago

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Hotels with Connecting Rooms

Our top choices for South Side hotels with connecting rooms

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.4 out of 10, Very good, (1,000 reviews)
"Staff very friendly "
United States
Kali
The price is €97
includes taxes & fees
17 Mar - 18 Mar
Holiday Inn Chicago – Midway Airport S by IHG

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
3.0 star property
Hyde Park
8.8 out of 10, Excellent, (1,002 reviews)
"The staff was awesome! The experience was AMAZING! "
United States
April
The price is €137
includes taxes & fees
19 Mar - 20 Mar
Hyatt Place Chicago-South/University Medical Center

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5 star property
Bedford Park
9.0 out of 10, Wonderful, (1,308 reviews)
"The breakfast was good, and the shuttle bus was very convenient."
United States
Shuchen
The price is €107
includes taxes & fees
23 Feb - 24 Feb
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Sophy Hyde Park

Sophy Hyde Park
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (1,002 reviews)
"The view and room was awesome."
United States
Merritt
The price is €219
includes taxes & fees
22 Feb - 23 Feb
Sophy Hyde Park

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1,009 reviews)
"Everything about the hotel was great. Awesome location and the staff was great!"
United States
Makessia
The price is €118
includes taxes & fees
5 Mar - 6 Mar
SpringHill Suites by Marriott Chicago Chinatown

Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (921 reviews)
"Great service, friendly staff. Great stay"
United States
Adrian
The price is €121
includes taxes & fees
28 Feb - 1 Mar
Chicago Marriott Midway

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, (2,384 reviews)
"Great stay"
United States
Blake
The price is €163
includes taxes & fees
22 Feb - 23 Feb
Sable at Navy Pier Chicago, Curio Collection by Hilton

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,207 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is €151
includes taxes & fees
24 Mar - 25 Mar
Swissotel - Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,286 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is €106
includes taxes & fees
22 Feb - 23 Feb
The Chicago Hotel Collection Ambassador Gold Coast

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,306 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is €172
includes taxes & fees
7 Mar - 8 Mar
Palmer House a Hilton Hotel
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