Southmoor Vacations from $360
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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.
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.
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.
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
"Really bad hotel. The rooms are old and smell, they are also tiny. If you ask for housekeeping- 50/50 chance that they visit. If you need room service, they will be rude on the call and their usual answer is ‘it will take an hour or longer’ even if you need something simple. Only one elevator works. ..."
Reviewed on Oct 9, 2026
Hilton Chicago
"Clean room and convenient to city walk."
Reviewed on Oct 9, 2026
Club Quarters Hotel, Central Loop, Chicago
"Clean, quiet, comfortable, convenient with great check-in service. Affordable. Great location. All you need."
Reviewed on Oct 8, 2026
Things to do
Wendella's 90-min Chicago River Architecture Tour
