Englewood Vacation Packages 2026 from $493

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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.

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

Save 100% on your flight

$493

per person

Nov 13 - Nov 15

found 14 hours 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

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$976

per person

Nov 28 - Dec 4

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (573 reviews)

We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.

Reviewed on Sep 26, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$867

per person

Nov 28 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,025 reviews)

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)

Amazing stay for a family of four. The kids loved the pool, and the adults loved the hot tub! It felt close to the action, without being too close. Quiet but walkable to Navy Pier, Michigan Avenue, etc. Nearby multiple grocery stores. The building was well maintained and the neighborhood felt safe. The views from the room were unbelievable (the pictures don't do them justice). I would definitely stay here again.

Reviewed on Sep 26, 2026

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$503

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,338 reviews)

Front desk staff was great as was housekeeping staff. Rooms were nothing special. Shower and bathroom floor had moldy grout. Bed was absolutely awful. Felt like sleeping on golfballs. Bar staff was awful. Wanted a quick drink while waiting for an Uber. Told them to charge to room. Bartender went MIA so we asked, what we assumed was a manager to ring us, he said ‘yep’ then went on to make some drinks, ignoring us. For the $$$ you can find much better hotels.

Reviewed on Sep 27, 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

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$186 nightly

$221 total

Oct 25 - Oct 26

Total with taxes and fees

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

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$179 nightly

$213 total

Oct 14 - Oct 15

Total with taxes and fees

See all 4,583 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.