South Side

Travel Guide

A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.
A mallard duck swimming in water.
A duck swimming in water with its reflection visible.
A mandarin duck swimming in calm water.
A baseball stadium with empty stands, a large digital scoreboard, and various advertisements.
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is HK$1,326 per night from 23 Sept to 24 Sept
HK$1,326
HK$1,557 total
23 Sept - 24 Sept
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the overall value in their reviews. ...
Chicago Lake Shore Hotel
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
The price is HK$1,192 per night from 27 Sept to 28 Sept
HK$1,192
HK$1,478 total
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff and the clean ...
Holiday Inn Chicago – Midway Airport S by IHG
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
The price is HK$1,344 per night from 21 Sept to 22 Sept
HK$1,344
HK$1,598 total
21 Sept - 22 Sept
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,359 reviews)
"Love the place, the employees, the restaurants, and the parking!"

Reviewed on 12 Sept 2026

Jaslin Hotel
See all 473 properties in South Side
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.
Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago

Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago

Chicago IL
Stay at this condo in Chicago. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Soldier Field and Griffin Museum of Science and Industry ...
8/10 Very good! (5 reviews)
"The queen beds were comfortable and the parking was easy. It was nice that there were so many bathrooms, so no one ever had to wait. There was no bedding for the futons/couch, we found a thin blanket to use as a sheet and we happened to bring a blanket with us, so we made do. In the common areas ..."

Reviewed on 10 Aug 2026

Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox

Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox

Chicago IL
Stay at this holiday home in Chicago. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (6 reviews)
"There was no issues during our stay and the rules are very reasonable. One thing to note is the location of the home which steps away from Chinatown, and a couple of minutes away from downtown. The home is very secure and spacious. The bathrooms, kitchen, and bedrooms were very clean. There was hot ..."

Reviewed on 21 Aug 2026

Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox
Bronzeville Manor walking distance to hospitals

Bronzeville Manor walking distance to hospitals

Chicago IL
Stay at this condo in Chicago. Enjoy free Wi-Fi. Popular attractions Soldier Field and Grant Park are located nearby.
9.6/10 Exceptional! (26 reviews)
"It was a lovely place to stay for my first time using VRBO. Will definitely stay here again next time I'm in Chicago."

Reviewed on 9 Aug 2026

Bronzeville Manor walking distance to hospitals
See all properties in South Side
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.

Stay near popular South Side attractions

A cityscape with historic buildings, a prominent church, and a view of the ocean.

University of Chicago

8.6/10 (3,689 reviews)
Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

HK$212
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

HK$1,129
per adult
94% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

HK$369
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Big Bus Chicago Hop-On Hop-Off Big Bus Tour

Big Bus Chicago Hop-On Hop-Off Big Bus Tour

HK$346
per adult
86% of travellers recommend
Big Bus Chicago Hop-On Hop-Off Big Bus Tour
Art Institute of Chicago

Art Institute of Chicago

HK$314
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago Explorer Pass: Save up to 50 Percent - Includes SkyDeck

Chicago Explorer Pass: Save up to 50 Percent - Includes Skydeck Chicago

HK$593
per adult
84% of travellers recommend
Chicago Explorer Pass: Save up to 50 Percent - Includes Skydeck Chicago
See all activities in South Side
A city skyline with modern skyscrapers and a river with boats and people in the foreground.

Chicago

A beach with waves, a clear sky, and tall grass in the foreground.

Whiting

A pier extending into calm waters at sunset with a clear sky.

Hammond

A city skyline with numerous high-rise buildings, a body of water in the foreground, and a sunset sky.

Calumet Park

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