Southmoor Vacations from $577
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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
Where to stay in Southmoor
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.
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.
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.
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.
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
Congress Plaza Hotel
"Great location, serious service and sanitation failures. Rooms are dated, which could be charming. The TV has basic channels only, so bring a Chromecast or Roku. The in room tablet is useless; that money should have gone to the TVs. Room service never came. I ordered biscuits and gravy and pancakes. ..."
Reviewed on Aug 25, 2026
Hilton Chicago
"The location of this hotel is incredible, and the amenities were great (very nice gym, pool, etc…all in good order). A few frustrations with our stay, housekeeping didn’t visit at all 2 of the 4 days we were there and we needed to contact the desk for towels etc… Also the street noise was VERY loud ..."
Reviewed on Aug 24, 2026
Crowne Plaza Chicago West Loop by IHG
"excellent stay! awesome staff!"
Reviewed on Aug 25, 2026
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
