A sunset over a calm lake with trees silhouetted against the sky.

Southmoor Vacations from $366

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    • Your Southmoor Vacation

    Prepare to experience Southmoor on your own terms with a custom Southmoor vacation package! Uncovering the best parts of this lively city is made easier with a base in a neighborhood such as Flossmoor, which is good for golfing, among other things. You'll want to do a little exploring during your trip to Southmoor. Don't miss leading attractions such as Orland Park Sportsplex, Orland Square and Centennial Park. A couple of quick clicks is all it takes to put together a tailored Southmoor vacation on Expedia.

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    Where to stay in Southmoor

    Find the best Southmoor areas and neighborhoods for the activities you enjoy most.

    A cityscape with tall skyscrapers and a historic tower.

    The Chicago Theatre with ornate architecture and a prominent marquee.

    A river with boats, surrounded by tall buildings and a clear sky.

    The Chicago Theatre with marquee lights and a large illuminated sign.

    A cityscape with a mix of modern skyscrapers and a historic tower.

    View properties in map for Downtown 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.

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    A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

    Photo by © City of Chicago

    A city intersection with tall buildings, including a historic building labeled "Water Tower Place."

    A cityscape with tall buildings, including a historic tower and modern skyscrapers.

    Photo by TM

    A cityscape with tall buildings, a prominent clock tower, and a busy intersection with moving vehicles.

    A nighttime cityscape with illuminated skyscrapers and a prominent clock tower.

    View properties in map for Magnificent Mile

    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.

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    A river with yellow boats, a bridge, and tall buildings.

    A nighttime cityscape with illuminated buildings and a bridge over a river.

    A nighttime cityscape with illuminated skyscrapers and a river.

    A river with a bridge, modern buildings, and a historic tower.

    A river with a yellow boat and a white yacht. In the background, there are tall buildings and a bridge.

    View properties in map for The Loop

    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.

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    A large, historic building with a central tower and multiple windows, located near a body of water.

    A city street with a train passing overhead, cars, pedestrians, and a red brick building.

    A nighttime cityscape with illuminated buildings, a river, and a bridge.

    Photo by Katie Robinson

    A modern building with illuminated signage, surrounded by urban skyscrapers and a curved road with light trails.

    Photo by LJ Alan

    A coastal cityscape with a long beach, dense urban buildings, and a clear blue sea.

    Photo by Robert Bartolino

    View properties in map for River North

    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.

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    A river with a city skyline in the background, surrounded by green trees and grass.

    A city skyline with a river, green spaces, and a baseball field.

    A city skyline with tall buildings, a frozen lake, and leafless trees in a park.

    A city skyline with high-rise buildings, a calm river reflecting the structures, and a park with trees and a walking path.

    A city skyline with a park and a lake.

    View properties in map for Lincoln Park

    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.

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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.