Southmoor Vacations from $645

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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.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$645

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,128 reviews)

The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.

Reviewed on Aug 21, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$801

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (550 reviews)

Great staff and amenities. Beautiful pool, bbq area and more. Terrific room Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them. For the money your room key or a key pad should allow you in.

Reviewed on Aug 21, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$880

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$709

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (157 reviews)

Beautiful room. Great location. Will be back.

Reviewed on Aug 22, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$780

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

Great stay on the river!

Reviewed on Aug 23, 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

$113 nightly

$135 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,288 reviews)

"Convenient to many attractions. Comfortable room. Fastest elevators! Favorite place to stay in Chicago!"

Reviewed on Aug 23, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$211 nightly

$251 total

Sep 7 - Sep 8

Total with taxes and fees

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

Fully refundable

$173 nightly

$205 total

Aug 30 - Aug 31

Total with taxes and fees

See all 2,416 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.