South Loop Vacations from $389
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Your South Loop Vacation
Cafes, bars and pubs and history are just the start of the things waiting for you when you lock in a vacation package to South Loop. Whether you're craving adventure, relaxation or something else, this commercial neighborhood is likely to have it. Not sure what to see and do during your trip to South Loop? Nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago are good places to begin. Expedia will help you turn your ideal South Loop vacation into reality, whatever your budget or travel plans.
The Latest South Loop Vacation Packages
Trump International Hotel & Tower Chicago
Reviewed on Sep 20, 2026
Level Chicago – Old Town
Reviewed on Sep 19, 2026
Where to stay in South Loop
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.
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.
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.
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.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
South Loop Hotel Deals
Congress Plaza Hotel
Hilton Chicago
"Outstanding hotel and amenities. Close to everything in the Loop. Would stay there again. 10/10"
Reviewed on Sep 20, 2026
Travelodge by Wyndham Downtown Chicago
"It needs a remodel and floors. The room smelled pretty bad maybe because of the carpet."
Reviewed on Sep 20, 2026
Stay near popular South Loop attractions
Soldier Field
McCormick Place
Field Museum of Natural History
Adler Planetarium and Astronomy Museum
Northerly Island Natural Area
Wintrust Arena
Columbia College Chicago
Arie Crown Theater
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
Explore a world of travel with Expedia
- Fisher Building
- Maggie Daley Park
- Old Colony Building
- Driehaus Museum
- Ronald McDonald House near Lurie Children’s
- Montrose Beach
- Chicago Symphony Orchestra
- Holy Name Cathedral
- The Loop Vacations
- Crown Fountain
- Marquette Building
- Depaul University-Loop Campus
- Symphony Center
- Buckingham Fountain
- South Commons Vacations
- Chinatown Vacations
- Richard J. Daley Center
- Tribune Tower
- Haskell Building
- Michigan Avenue Bridge
- Chicago Loop Synagogue
- American Police Center & Museum
- Shops at North Bridge
- Chicago Museum Campus Vacations
- Cloud Gate
- Merchandise Mart
- Downtown Chicago Vacations
- Art Institute of Chicago
- Sullivan Center
- Chase Tower
- Chicago History Museum
- Film Row Cinema
- Aon Center
- Oak Street Beach
- Navy Pier
- Marina City
- Maxwell Street Market
- Michigan Avenue
- Unity Temple
- Marshall Field Building
- Carbide and Carbon Building
- Pontiac Building
- Roosevelt University
- United Center
- Lincoln Park Zoo
- Magnificent Mile Vacations
- Willis Tower
- Lincoln Park Conservatory
- Bally's Casino Chicago
- Water Tower Place
- North Avenue Beach
- Chicago Architecture Foundation
- Chicago Vacations
- Wrigley Field
- Auditorium Building and Theatre
- Cna Center
- Columbia College Chicago
- State Street
- Chicago Temple
- Harold Washington Library Center
- Goodman Theater
- Civic Opera House
- Skydeck Ledge
- Daley Plaza
- Chicago Board of Trade Building
- Chicago Place Mall
- Ping Tom Memorial Park
- The East Bank Club
- Robie House
- Chicago Children's Museum
- The Salt Shed
- Chicago Harbor Lighthouse
- Lakefront Trail
- Chicago Cultural Center
- Cibc Theatre
- Grant Park
- Chicago Riverwalk
- University of Illinois Chicago
- Fourth Presbyterian Church
- Chicago Water Tower
- Chicago City Hall
- Theatre District Vacations
- Mary Bartelme Park
- Ohio Street Beach
- 900 North Michigan Shops
- Burnham Park
- 333 West Wacker Drive
- 311 S Wacker Dr
- Northwestern Memorial Hospital
- Wrigley Building
- Millennium Park
- Picasso Statue
- Gen. John Logan Memorial
- Santa Fe Building
- House of Blues Chicago
- Jane Addams' Hull-House Museum
- Cadillac Palace Theatre
- Monadnock Building
- Rookery