Southmoor Vacations from $425
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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
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
"They don't have a frickin' thermostat and the AC is an archaic, barely functioning hunk of metal. The curtains don't keep out the light (and the street is very bright) and the noise from the street is barely quieted at all. The shower floor looked sketchy, so we showered in flip-flops. Aside from ..."
Reviewed on Sep 12, 2026
Hilton Chicago
Club Quarters Hotel, Central Loop, Chicago
"This hotel was a bit disapointing. The room price was on the higher end and the room did not reflect that. It was very dated, everything was very worn out, the staff was not very helpful and you have to do check-in by yourself even though the staff is there. We had bought the breakfast as an extra ..."
Reviewed on Sep 12, 2026
Things to do
