South Chicago Vacations from $452
Book a Hotel + Flight or Car together to unlock savings
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.
Pendry Chicago
Downtown Chicago
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
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
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
South Chicago Hotel Deals
Congress Plaza Hotel
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! (10,146 reviews)
"We stayed at the buckinham wing of the hotel. It’s an old hotel. The water runs brown for the first few seconds . The curtains were bright silver. Not what I expected. The best part is the location ."
Reviewed on Nov 9, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 11 to Nov 12
$138 total
Nov 11 - Nov 12
Total with taxes and fees
8/10 Very Good! (2,692 reviews)
"Great stay! Will return"
Reviewed on Nov 9, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Dec 10 to Dec 11
$126 total
Dec 10 - Dec 11
Total with taxes and fees
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
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
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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.