Southmoor Vacations from $515

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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

$515

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

Great location and pleasant staff.

Reviewed on Aug 17, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$737

per person

Oct 21 - Oct 25

found 1 day 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

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$610

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Overall, this is a great hotel. My family loved the rooms and the fitness center. The staff were mostly great too. We will definitely stay here again if we come back to Chicago. We were given rooms that were 28 floors apart despite making our reservation months in advance. Yes, it was one reservation which included 2 rooms. Both the shower and toilet space was fairly tight. Other than that, we are very happy.

Reviewed on Aug 18, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$554

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay. Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that. Overall a great spot. Affordable and lots of space with great views!

Reviewed on Aug 15, 2026

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$1,189

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on Aug 16, 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

8/10 Very Good! (10,247 reviews)

"Hotel needs to be renovated.. it’s in really rough shape. ..actual spider webs on the windows.. smells bad.. it’s wild.."

Reviewed on Aug 17, 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! (3,066 reviews)

"Waited a long time to check in. Loved the games in the lobby! Pool was great! Housekeeping didn’t clean our room on the second night- we came back to a dirty room with no sheets in a bed and the do not disturb sign was on the door. I called the front desk, but no one came so then I had to go track ..."

Reviewed on Aug 18, 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! (2,523 reviews)

"The staff was very helpful! They were able to hold our bags after checkout since we had later flights."

Reviewed on Aug 18, 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.