Southmoor Vacation Packages 2026 from $493

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.

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

Save 100% on your flight

$493

per person

Nov 13 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,001 reviews)

Staff were amazing, helpful and accommodating.

Reviewed on Sep 25, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$646

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,025 reviews)

beautiful property in a great location highly recommend staying here this will be our go to spot when visiting chicago

Reviewed on Sep 28, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$976

per person

Nov 28 - Dec 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (573 reviews)

👍

Reviewed on Sep 28, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$621

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (527 reviews)

The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

Le Méridien Essex Chicago

Downtown Chicago

Save 100% on your flight

$548

per person

Nov 30 - Dec 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (1,004 reviews)

Great location to walk to concert at Northerly Island. Staff was very friendly and hotel was updated nicely

Reviewed on Sep 28, 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

$157 nightly

$187 total

Oct 26 - Oct 27

Total with taxes and fees

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$188 nightly

$221 total

Oct 24 - Oct 25

Total with taxes and fees

8.6/10 Excellent! (3,299 reviews)

"They charged $29 without any explanation. I didn’t know food credit or anything. After I checked out that charged. What is destination fee? If you want sell something, you have to tell me what you are selling to me."

Reviewed on Sep 28, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

Fully refundableReserve now, pay when you stay

$199 nightly

$237 total

Oct 4 - Oct 5

Total with taxes and fees

See all 2,463 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.