Englewood Vacation Packages 2026 from $276

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Your Englewood Vacation

Make travel planning stress-free by snapping up a vacation package to Englewood. Let us look after the minutiae, so you can concentrate on soaking up everything this neighborhood can offer. Hoping to sightsee during your trip to Englewood? Be sure to stop by nearby attractions such as University of Chicago, Robie House and 4944 S Woodlawn Ave. Don't just wish for it — do it! Book your perfect Englewood vacation with Expedia and travel your way.

The Latest Englewood Vacation Packages

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$276

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,334 reviews)

St. Clair hotel lists the room as premium, even though the two windows in the room had no view. Both windows faced the building outter exterior brick walls from all sides. Dim lightning with no direct sunlight, very depressing to look out. The room should have been listened and offered as standard, at best, not premium.

Reviewed on Oct 24, 2026

Sheraton Grand Chicago Riverwalk

Downtown Chicago

$702

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,873 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$382

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (591 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

$385

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

The hotel was very nice and private, the workers were nice and friendly. We got to check in early and get right in. The breakfast was also great. Really enjoyed my stay

Reviewed on Oct 25, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$316

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

We liked the location and the hotel itself. The front desk staff were great. It was nice not to be cooped up in a hotel room for a lengthy stay. We really enjoyed it!

Reviewed on Oct 24, 2026

Where to stay in Englewood

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

Englewood Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$104 nightly

$124 total

Nov 11 - Nov 12

Total with taxes and fees

8/10 Very Good! (10,104 reviews)

"Pleasant stay great location"

Reviewed on Oct 25, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$122 nightly

$145 total

Nov 22 - Nov 23

Total with taxes and fees

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$116 nightly

$138 total

Nov 22 - Nov 23

Total with taxes and fees

8.8/10 Excellent! (5,566 reviews)

"Best location possible. Loved the river and night skyline."

Reviewed on Oct 25, 2026

See all 4,737 properties in 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.