Southmoor Vacation Packages 2026 from $389

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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.

Chicago Lake Shore Hotel

Kenwood

Save 100% on your flight

$389

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7/10 Good! (1,004 reviews)

My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!

Reviewed on Sep 22, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$656

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!

Reviewed on Sep 19, 2026

Stay One Chicago

Downtown Chicago

Save 100% on your flight

$1,088

per person

Nov 26 - Dec 1

found 24 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.8/10 Good! (12 reviews)

Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on Sep 20, 2026

Silversmith Hotel Chicago Downtown

Downtown Chicago

Save 100% on your flight

$816

per person

Nov 28 - Dec 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (2,381 reviews)

Kinzie Hotel

Downtown Chicago

Save 100% on your flight

$543

per person

Nov 26 - Dec 1

found 24 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (2,169 reviews)

The location of the hotel is perfect with easy access to most attractions. The staff was very nice. The room was clean. The facility is a little run down and we did wonder why every time we turn on the light on the bathroom there was a loud noise , it turns out that it was the fan and they do have a sign to notify guests including a night light so you don't have to turn the light on if you are just going in and out. The cocktail reception every day is a plus. I would stay again.

Reviewed on Sep 22, 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 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 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 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

$188 nightly

$223 total

Sep 27 - Sep 28

Total with taxes and fees

8/10 Very Good! (10,192 reviews)

"I’ve stayed here for years. Every riot"

Reviewed on Sep 22, 2026

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$208 nightly

$248 total

Oct 24 - Oct 25

Total with taxes and fees

8.6/10 Excellent! (3,252 reviews)

"We had a delightful stay."

Reviewed on Sep 23, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Sep 27 - Sep 28

Total with taxes and fees

8.6/10 Excellent! (1,013 reviews)

"The hotel was absolutely stunning! Loved the convenience of it being right down town!"

Reviewed on Sep 22, 2026

See all 2,449 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.