Southmoor Vacations from $525

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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

$525

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,089 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$782

per person

Oct 21 - Oct 25

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$710

per person

Nov 2 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

A+

Reviewed on Aug 20, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$588

per person

Oct 22 - Oct 25

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Beautiful room & View!! Will definitely book again!

Reviewed on Aug 19, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$786

per person

Oct 21 - Oct 25

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy

Reviewed on Aug 19, 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

$109 nightly

$130 total

Sep 8 - Sep 9

Total with taxes and fees

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$197 nightly

$231 total

Sep 7 - Sep 8

Total with taxes and fees

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

Fully refundableReserve now, pay when you stay

$173 nightly

$205 total

Aug 30 - Aug 31

Total with taxes and fees

9/10 Wonderful! (2,525 reviews)

"Some of the staff at the front desk were very rude. The cleaning staff were great very accommodating. The front desk manager was accommodating. We had to request him to get results. We requested conjoined rooms and was told they didn't have any after speaking to the manager we were able to move to ..."

Reviewed on Aug 20, 2026

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.