A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Search Hotels with Entertainment in South Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Hotels with Entertainment

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for South Side hotels with entertainment

Terrace/patio

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, (2,556 reviews)
"The location was very convenient"
United States
Jeffrey
The price is £214
includes taxes & fees
1 Jul - 2 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,443 reviews)
The price is £245
includes taxes & fees
1 Jul - 2 Jul
Hyatt Regency Chicago
2 restaurants; breakfast, lunch and dinner served

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,753 reviews)
"Great location!"
United States
William
The price is £236
includes taxes & fees
5 Jul - 6 Jul
LondonHouse Chicago, Curio Collection by Hilton
Breakfast and dinner served

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,828 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is £163
includes taxes & fees
5 Jul - 6 Jul
Omni Chicago Hotel
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,133 reviews)
"Excellent hotel! Will definitely stay again."
United States
Justin
The price is £166
includes taxes & fees
5 Jul - 6 Jul
Arlo Chicago
Lobby

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,001 reviews)
"All around great stay. "
United States
Nicholas
The price is £128
includes taxes & fees
2 Jul - 3 Jul
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Lobby

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,264 reviews)
"Excellent place to stay, as we found it central & walkable to most parks & attractions. The place was spotless & the staff were fantastic."
Canada
Jody
The price is £141
includes taxes & fees
5 Jul - 6 Jul
River Hotel
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,423 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is £178
includes taxes & fees
5 Jul - 6 Jul
Swissotel - Chicago
55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,247 reviews)
"I would absolutely stay here again! Beautiful well thought out property, within walking distance of everything."
United States
Joel
The price is £218
includes taxes & fees
5 Jul - 6 Jul
L7 Chicago by LOTTE
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,467 reviews)
"Great stay!"
United States
Avradita
The price is £147
includes taxes & fees
8 Jul - 9 Jul
Hilton Chicago/Magnificent Mile Suites
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

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

8/10 Good
"I had asked for a roll away bed, as we had 3 adults. One was only staying for 1 night and we needed that bed for that night. The bed wasn’t delivered, and there was only 1 person on staff, and that was the check-in person. Needless to say we didn’t get the bed delivered. Luckily, the guy with us always has a blow up mattress in his trunk as he camps frequently. The bed was delivered the next day while we were gone, but we didn’t need it any longer. Our room wasn’t cleaned that day, which was an issue, but I didn’t say anything. We were too tired after our busy day to even care. The next morning was checkout. We slept until 10:45, and when I called to ask what time checkout was, was told it was 11a. The desk person was gracious enough to give us until 12 noon, since we had just gotten up. We turned in our parking papers, and room keys with 10 minutes to spare. All in all, it was a pleasant stay. I would stay again. OHHH-the hotel does put a $100 charge on your card for incidentals-and I used my debit card, which takes 7-14 days for the charge to fall off and be returned. That wasn’t told to me in advance, and limited my spending. I know now to ask when I book anywhere."
Candette 2-night trip
Posted 3 hours ago
Chicago Lake Shore Hotel

Explore a world of travel with Expedia