Southmoor Vacations from $660

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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

Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$660

per person

Nov 5 - Nov 9

found 19 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.2/10 Wonderful! (556 reviews)

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

Reviewed on Sep 1, 2026

Kimpton Gray Hotel by IHG

Downtown Chicago

$1,181

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

The room was very clean and spacious. Staff was very informative about what was accessible during our stay. I would definitely stay here again if I come back to visit Chicago.

Reviewed on Sep 1, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$1,678

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,003 reviews)

The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍

Reviewed on Sep 2, 2026

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$1,137

per person

Nov 5 - Nov 8

found 23 hours 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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$1,159

per person

Oct 10 - Oct 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!

Reviewed on Sep 2, 2026

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

Fully refundableReserve now, pay when you stay

$112 nightly

$133 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,264 reviews)

"The room itself was small, but perfectly serviceable for a couple intending to spend more time in the city than the hotel room. The parking however was *extremely* expensive and was not in and out, so if we wanted to use the car we would have had to pay the parking again. There were no washcloths ..."

Reviewed on Sep 3, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$194 nightly

$230 total

Sep 10 - Sep 11

Total with taxes and fees

8.6/10 Excellent! (3,133 reviews)

"The location was geeat"

Reviewed on Sep 3, 2026

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

Fully refundable

$109 nightly

$129 total

Sep 8 - Sep 9

Total with taxes and fees

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.