Southmoor Vacations from $538

Book a Hotel + Flight or Car together to unlock savings

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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$538

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

The property was well maintained and very clean.

Reviewed on Sep 4, 2026

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$1,140

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.

Reviewed on Sep 2, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$660

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.2/10 Wonderful! (561 reviews)

Loved the hotel, super nice and clean! Felt like home away from home!

Reviewed on Sep 1, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$548

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$806

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,577 reviews)

Where to stay in Southmoor

Find the best Southmoor areas and neighborhoods for the activities you enjoy most. Learn more about Southmoor

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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 neon sign reading "Blue Chicago on Clark" in an ornate archway.

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 city street with a train passing overhead, cars, pedestrians, and a red brick building.

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 wooden pavilion with a view of a city skyline and a body of water.

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

520 South Michigan Avenue Chicago IL

$115 nightly

$136 total

Sep 7 - Sep 8

Total with taxes and fees

8/10 Very Good! (10,269 reviews)

"Nice"

Reviewed on Sep 4, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

$227 nightly

$266 total

Sep 8 - Sep 9

Total with taxes and fees

8.6/10 Excellent! (3,141 reviews)

"Overall great experience staying here. The view was really nice and the room was spacious and clean. Loved that it was walking distance from the stadium."

Reviewed on Sep 4, 2026

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

$128 nightly

$152 total

Sep 8 - Sep 9

Total with taxes and fees

8.8/10 Excellent! (3,649 reviews)

"Great location, mostly walking distance to the sightseeing spots"

Reviewed on Sep 4, 2026

See all 2,426 properties in Southmoor

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.