South Side Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Hyde Park

Hyde Park

4 out of top 10 points of interest in this area
3/5(1 area review)

Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.

Find hotels in Hyde Park

Top hotels in South Side

Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
9/10 Wonderful! (1,222 reviews)
Friendly staff and great location if u want to explore Chicago’s Chinatown but it’s also closer to downtown Chicago as well. Lots of amazing food choices and cheap parking around the area compared to the rest of Chicago.

Reviewed on 11 May 2026

Get rates
Jaslin 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
Fully refundable
The price is 3.683.260 ₫ per night from 24 May to 25 May
3.683.260 ₫
4.586.974 ₫ total
24 May - 25 May
includes taxes & fees
8.2/10 Very Good! (1,021 reviews)
It was in a good location right next to a bus stop but it looked like they were fixing the place up and I’m sure it will be great when it’s done but it’s not there yet

Reviewed on 9 May 2026

Holiday Inn Chicago – Midway Airport S by IHG
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is 3.393.861 ₫ per night from 19 May to 20 May
3.393.861 ₫
3.984.054 ₫ total
19 May - 20 May
includes taxes & fees
6.8/10 (1,008 reviews)
This is an older 2 story property with great big refinished rooms with lake views. Daily attention to room turndown excellent! Front desk staff very nice. Location is wonderful with the highway close, biking path and water close, food a short walk, and museums a short drive. Parking is free. Downside ...

Reviewed on 11 May 2026

Chicago Lake Shore 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.

Popular places to visit

Griffin Museum of Science and Industry

Griffin Museum of Science and Industry

You can spend an afternoon exploring the galleries in Griffin Museum of Science and Industry in Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Griffin Museum of Science and Industry
Rate Field

Rate Field

Catch an event at Rate Field during your trip to Chicago. Experience the fascinating museums and acclaimed art galleries in this vibrant area.

Rate Field
613-28 Japanese Island Jackson Park Chicago

Jackson Park

Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Jackson Park

Explore a world of travel with Expedia