South Chicago Vacations from $370

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Your South Chicago Vacation

South Chicago is calling! Whatever type of getaway you're organizing, get ready to discover the best of this neighborhood with a South Chicago vacation package. When it's time to get out and explore, you'll find lots of big-name attractions nearby including Calumet Park, Calumet Beach and Munson Beach. Visit one, two (or even all!) during your trip to South Chicago. Expedia is here to put your plans into action. Book your ideal South Chicago vacation today.

The Latest South Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hotel Riu Plaza Chicago
Park Hyatt Chicago
Le Méridien Essex Chicago

Where to stay in South Chicago

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

South Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,108 reviews)
"Beautiful hotel. Asked for adjoining rooms and was accommodated. Comfortable beds and pillows. Would stay again."

Reviewed on Nov 6, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 9 to Nov 10
$138 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (2,668 reviews)
"Nice area"

Reviewed on Nov 6, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundable
$115 nightly
The price is $137 total per night from Dec 6 to Dec 7
$137 total
Dec 6 - Dec 7
Total with taxes and fees
8.8/10 Excellent! (5,584 reviews)
"Great location. Staff was welcoming. Room was perfect"

Reviewed on Nov 6, 2026

River 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.

Things to do

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.