South Englewood Vacations from $427

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The Latest South Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Chicago Lake Shore Hotel

Kenwood

Save 100% on your flight

$427

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7/10 Good! (1,004 reviews)

I'll keep it straight forward. The staff was friendly and helpful. The room was clean and simple with refrigerator, microwave and coffee maker. Good house keeping each day. King size bed had a firm mattress that was fairly comfortable but the pillows were so so. The air-conditioning was good. The only downside I found was the shower water pressure was very low but it got the job done so not really a big deal. Over all a good place to stay at a great price.

Reviewed on Sep 24, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$645

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (561 reviews)

Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!

Reviewed on Sep 24, 2026

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$636

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,146 reviews)

Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.

Reviewed on Sep 23, 2026

Stay One Chicago

Downtown Chicago

Save 100% on your flight

$1,151

per person

Nov 26 - Dec 1

found 1 day 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

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$448

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,338 reviews)

Where to stay in South Englewood

Find the best South Englewood areas and neighborhoods for the activities you enjoy most. Learn more about South Englewood

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.

South Englewood Hotel Deals

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$169 nightly

$201 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (5,435 reviews)

"Elevator was broken, took 15 minutes each time I needed it"

Reviewed on Sep 24, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$153 nightly

$182 total

Oct 25 - Oct 26

Total with taxes and fees

8/10 Very Good! (10,201 reviews)

"Not well thought or planned for the convenience of the traveler. For example there was way to control the room temperature, sheets were short for tall people"

Reviewed on Sep 24, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$161 nightly

$191 total

Oct 25 - Oct 26

Total with taxes and fees

8/10 Very Good! (2,318 reviews)

"Much better experience than anticipated based off of reviews. Great location!"

Reviewed on Sep 24, 2026

See all 4,451 properties in South Englewood

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.