South Chicago Vacations from $267
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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
Where to stay in South Chicago
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of 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.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
South Chicago Hotel Deals
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast
The Allegro Royal Sonesta Hotel Chicago Loop
"Room was ok but cramped. Closet was tiny. The bigger issue was the keycard system was down when I checked in and had to wait > 1 hr to get my key card. Otherwise an ok stay. Would prefer if they had a coffee machine in the room."
Reviewed on Aug 6, 2026
Stay near popular South Chicago attractions
Mahalia Jackson Residence
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
Explore a world of travel with Expedia
- Robie House
- Obama's House
- Old Colony Building
- South Commons Vacations
- Rockefeller Memorial Chapel
- Lorado Taft's Midway Studios
- Tribune Tower
- Driehaus Museum
- The Salt Shed
- Wrigley Building
- Roosevelt University
- Art Institute of Chicago
- Lincoln Park Conservatory
- Jane Addams' Hull-House Museum
- Daley Plaza
- Sr Crown Hall
- Dusable Museum of African-American History
- Richard J. Daley Center
- Picasso Statue
- Bridgeport Art Center
- Rookery
- Downtown Chicago Vacations
- Gen. John Logan Memorial
- Navy Pier
- Ida B Wells House
- Chinatown Vacations
- Chicago City Hall
- Symphony Center
- Burnham Park
- Maxwell Street Market
- Lakefront Trail
- Film Row Cinema
- Maggie Daley Park
- Monadnock Building
- University of Chicago
- Unity Temple
- Willis Tower
- Jackson Park
- Civic Opera House
- Montrose Beach
- Elijah Muhammad House
- Columbia College Chicago
- Grant Park
- Chicago Architecture Foundation
- 311 S Wacker Dr
- Ohio Street Beach
- House of Blues Chicago
- The Loop Vacations
- Buckingham Fountain
- Robert W Roloson Houses
- Michigan Avenue
- University of Illinois Chicago
- Millennium Park
- Pontiac Building
- Cibc Theatre
- South Loop Vacations
- 333 West Wacker Drive
- Carbide and Carbon Building
- Chicago Cultural Center
- Water Tower Place
- Chicago Museum Campus Vacations
- Chicago Symphony Orchestra
- Griffin Museum of Science and Industry
- Auditorium Building and Theatre
- Cna Center
- Magnificent Mile Vacations
- Shops at North Bridge
- Lincoln Park Zoo
- Chicago Vacations
- Crown Fountain
- Chicago Place Mall
- Marina City
- Ping Tom Memorial Park
- American Police Center & Museum
- Chicago Loop Synagogue
- Holy Name Cathedral
- Wrigley Field
- Chicago Children's Museum
- Marshall Field Building
- Ronald McDonald House near Lurie Children’s
- Santa Fe Building
- Mccormick Tribune Center
- Goodman Theater
- Fisher Building
- Chicago Riverwalk
- Muddy Waters’ House
- 900 North Michigan Shops
- Depaul University-Loop Campus
- Zhou B Art Center
- Garden of the Phoenix
- Merchandise Mart
- Skydeck Ledge
- North Avenue Beach
- Michigan Avenue Bridge
- Canalport Riverwalk Park
- Cadillac Palace Theatre
- Chase Tower
- Grace Abbott Homes Vacations
- Hyde Park Vacations