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

Southmoor Vacations from $279

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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.

The Latest Southmoor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel with a prominent 'HOTEL FELIX' sign, surrounded by tall buildings and a tree-lined street.
    Dec 10 - Dec 13

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.4/10 - Very good (3,164 reviews)
    "This boutique hotel is located in a great area. Our main complaint is the hotel is old and therefore it’s not insulated from noise. We could hear every conversation, siren and party that went on in the streets. Our neighbor was a big snorer so that wasn’t pleasant. Our original room was just outside the elevator, which I did not like but the staff quickly moved us to another room, so that was great. Other than that we enjoyed our stay for the convenience. Lots of great restaurants within..."
    Reviewed November 5, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $422
    $279
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • A modern hotel entrance with a prominent sign reading "RIU PLAZA CHICAGO".
    Dec 10 - Dec 13

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,651 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $729
    $453
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • A cityscape with modern high-rise buildings, a river, and a bridge.
    Dec 10 - Dec 13

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,879 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $599
    $378
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • A room with two chairs and a small table, a large window with a city view at night.
    Dec 10 - Dec 13

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (3,989 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $629
    $404
    per traveler
    found 1 day ago
    Eurostars Magnificent Mile
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Dec 24 - Dec 29

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (604 reviews)
    "Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen"
    Reviewed November 6, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $857
    $557
    per traveler
    found 1 day ago
    Level Chicago Fulton Market

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.

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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City 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.

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

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.

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

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.

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

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.

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