Southmoor Vacation Packages 2026 from $271

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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.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

$271

per person

Nov 22 - Nov 25

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,015 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$823

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.

Reviewed on Oct 7, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$694

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

8.6/10 Excellent! (1,011 reviews)

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Save 100% on your flight

$357

per person

Dec 9 - Dec 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (2,884 reviews)

Chicago Lake Shore Hotel

Kenwood

$757

per person

Dec 21 - Dec 28

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Chicago (ORD)

7/10 Good! (1,018 reviews)

Definitely a motel vibe, no elevator. Nice staff and clean rooms.

Reviewed on Oct 5, 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

$111 nightly

$132 total

Nov 2 - Nov 3

Total with taxes and fees

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$190 nightly

$226 total

Oct 30 - Oct 31

Total with taxes and fees

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

Fully refundableReserve now, pay when you stay

$110 nightly

$131 total

Nov 1 - Nov 2

Total with taxes and fees

8.8/10 Excellent! (3,676 reviews)

"perfect stay, would recommend"

Reviewed on Oct 7, 2026

See all 2,473 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.