A pier with a lighthouse, a kite surfer, and a clear sky.

West Wing Estates Vacations from $401

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Your West Wing Estates Vacation

West Wing Estates is calling! Whatever type of getaway you're planning, you can discover more of this neighborhood with a West Wing Estates vacation package. Not sure what to see and do during your trip to West Wing Estates? Nearby attractions such as South Beach, Kal Haven Trail and South Haven Lighthouse are excellent places to start. Expedia is here to help put your plans into action. Book your ideal West Wing Estates vacation today.

The Latest West Wing Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A rooftop lounge with outdoor seating and a city skyline view.
    Dec 16 - Dec 19

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,161 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $609
    $401
    per traveler
    found 1 day ago
    Pendry Chicago
  • An outdoor seating area with a glass table, orange cushions, and potted plants.
    Dec 20 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,874 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,483
    $471
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.
    Dec 24 - Dec 29

    The Emily Hotel + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,356 reviews)
    "Staff was friendly and the room was clean"
    Reviewed November 3, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $830
    $508
    per traveler
    found 1 day ago
    The Emily Hotel
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Jan 5 - Jan 10

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (601 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $640
    $404
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Jan 15 - Jan 19

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (5,641 reviews)
    "We thoroughly enjoyed our stay at the Riu Hotel. The location was fantastic. You could go shopping or walk to the lakefront in 5 minutes. The rooms were modern and immaculate. The breakfast was included in our reservation and was great. We were also able to enjoy the rooftop bar with a heater. We would definitely recommend staying here"
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $654
    $419
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago

Where to stay in West Wing Estates

Find the best West Wing Estates areas and neighborhoods for the activities you enjoy most.
A coastal bridge at sunset with a calm sea and street lamps.

North Side

While visiting North Side, you might make a stop by sights like North Beach and Michigan Maritime Museum.

A lighthouse at sunset on a pier extending into the water.
Photo by Lawrence Tellez
Open Photo by Lawrence Tellez

Downtown

If you're spending some time in Downtown, Warner Vineyards and South Haven Center for the Arts are top sights worth seeing.

A pier extending into the water at sunset with a lighthouse in the distance.

South Side

If you're spending some time in South Side, South Beach and Southside Municipal Marina are top sights worth seeing.

A beach at sunset with a wooden fence and a distant lighthouse.

Miami Park

While Miami Park isn't home to many top sights, Kal Haven Trail and North Beach are some notable places to visit nearby.

A red lighthouse on a pier with the ocean in the background.

Mt. Pleasant

When in Mt. Pleasant, you can plan a visit to Kal Haven Trail and North Beach, some noteworthy sights in the nearby area.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.