Southmoor Vacations from $422

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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 Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$422

per person

Oct 16 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,899 reviews)

I loved Chicago but our sink did not drain, the air conditioning made a horrendous noise all night every time it came on and off and to make matters worse, we were close to the elevators which were also extremely noisy. Basically no sleep.

Reviewed on Aug 14, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$716

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$725

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$595

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Hotel amenities were great, and the suite was nice enough. The mattress was a little springy, but not terrible. I was frustrated by finding out about an amenities fee at the end that added roughly $100 to my cost at the hotel. That felt a lot like the “hidden fee” that so many booking services seek to advertise not having. That hotel would probably say that they don’t hide that fee, that it’s stated in the hotel stay conditions or something to that affect; but I’d argue that most people staying there for the first time are probably unaware of the fee prior to coming. If they want to charge an additional amount for the amenities at the hotel (which I admit are great), put the cost for the amenities into the price per night for the room itself. If you advertise the amenities at the hotel as a perk of staying there, consider that part of the upfront price rather than something that’s informed to you as you check out.

Reviewed on Aug 14, 2026

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$438

per person

Oct 4 - Oct 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,089 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

Fully refundableReserve now, pay when you stay

$109 nightly

$130 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,195 reviews)

"The hotel is actively being renovated. Our first room was outdated and the TV didn’t work. Because of the TV issue, we were moved to another room that was renovated much more recently. The staff were friendly and helpful. However, keep an eye out for pests. My mother found a roach in her room. We ..."

Reviewed on Aug 15, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$194 nightly

$230 total

Sep 7 - Sep 8

Total with taxes and fees

8.6/10 Excellent! (3,039 reviews)

"Great location, amazing staff"

Reviewed on Aug 15, 2026

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! (2,506 reviews)

"Parking sucks! No pool. But staff was satisfactory. Except for 1 guy who was over the top. Loved location. Overall great place convenient location. We would stay there again."

Reviewed on Aug 15, 2026

See all 2,408 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.