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

Southmoor Vacations from $340

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 grand lobby with a central bar, high ceilings, and classical architecture.
    Jan 15 - Jan 19

    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,001 reviews)
    "Clean room. Had the two queen bed room and wasn’t too small. Only needed a mini frig. Overall good experience"
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $534
    $340
    per traveler
    found 1 day ago
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
  • 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 (1,357 reviews)
    "Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"
    Reviewed November 4, 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 (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
    Save 100% on your flight
    $640
    $404
    per traveler
    found 2 days ago
    Level Chicago Fulton Market
  • A grand hallway with marble floors and a central staircase with a balustrade.
    Dec 24 - Dec 29

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $735
    $470
    per traveler
    found 1 day ago
    Kimpton Gray Hotel by IHG

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.

Southmoor Hotel Deals

A breakfast area with a counter, a sign that says 'HAPPY BREAKFAST STARTS HERE', and various food items displayed.

Hampton Inn Chicago Orland Park

Hampton Inn Chicago Orland Park
2.5 star property
4.1 mi from Southmoor
9.0 out of 10, Wonderful, (1,051 reviews)
$103 nightly
The price is $115
Nov 20 - Nov 21
Total with taxes and fees
Hampton Inn Chicago Orland Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Southmoor
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.