Near South Side Vacations from $787
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Your Near South Side Vacation
Lock in a vacation package to Near South Side and immerse yourself in everything this lakeside neighborhood has to offer. Noted for its history, walking and culture, your next exciting adventure can be found right here. Start your trip to Near South Side by checking out nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help turn your ideal Near South Side vacation into reality, no matter your travel plans or budget.
The Latest Near South Side Vacation Packages
Hotel Riu Plaza Chicago
Reviewed on Aug 29, 2026
Where to stay in Near South Side
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.
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.
Near South Side Hotel Deals
Hyatt Regency McCormick Place Chicago
Congress Plaza Hotel
"Cool old building with lots of history; however, the room was freezing cold with no ability to adjust the temperature, the water never stayed hot, the bed was firm like a board, and the tub clogged so we were showering with 3 inches of standing water. Regardless, the staff was kind and it did the ..."
Reviewed on Aug 29, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Stay near popular Near South Side attractions
Soldier Field
McCormick Place
Field Museum of Natural History
Adler Planetarium and Astronomy Museum
Northerly Island Natural Area
Northerly Island
Wintrust Arena
Arie Crown Theater
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
