Englewood Vacation Packages 2026 from $408

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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 Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$408

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$459

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,523 reviews)

The hotel is very centrally located! We got a room with a view and so worth it. Get the lake view you won’t be disappointed! Will definitely stay there again!

Reviewed on Oct 11, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$976

per person

Dec 20 - Dec 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (532 reviews)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Save 100% on your flight

$424

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,015 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$522

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

The hotel was really nice. Wish that parking was included.

Reviewed on Oct 6, 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

$106 nightly

$126 total

Nov 11 - Nov 12

Total with taxes and fees

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$152 nightly

$181 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (5,521 reviews)

"Great hotel"

Reviewed on Oct 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Nov 1 - Nov 2

Total with taxes and fees

See all 4,615 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.