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

West Wing Estates Vacations from $404

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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 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 (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $640
    $404
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • A modern lobby with a sofa, coffee table, and potted plants.
    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
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Jan 22 - Jan 25

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,642 reviews)
    "Excellent hotel in an excellent location. Close to all the attractions. Fabulous size room with the most comfiest bed! All the amenities you need are already in the room. Only complaint was the shower pressure was low. Other than that it was fabulous. Excellent breakfast included - fantastic selection! Would definitely recommend this hotel."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $720
    $475
    per traveler
    found 2 days ago
    Hotel Riu Plaza Chicago
  • A rooftop lounge with outdoor seating and a city skyline view.
    Jan 15 - Jan 19

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,161 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $752
    $509
    per traveler
    found 2 days ago
    Pendry Chicago
  • A modern kitchen with a large island, bar stools, and a city view.
    Dec 16 - Dec 19

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (557 reviews)
    "Estuvo muy increíble, fue una experiencia maravillosa.Es un lugar precioso me encantó"
    Reviewed November 1, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $601
    $411
    per traveler
    found 1 day ago
    Level Chicago – Old Town

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.