West Englewood Vacations from ¥387,655

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The Latest West Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥387,655
per person
Nov 15 - Nov 20
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
What an amazing hotel it is!! I just loved it. Might go again to Chicago and stay at RIU plaza❤️

Reviewed on Aug 25, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
¥490,112
per person
Oct 7 - Oct 13
found 5 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,335 reviews)
Arlo Chicago

Arlo Chicago

Downtown Chicago
¥479,724
per person
Oct 7 - Oct 13
found 5 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,234 reviews)
Loved how everything was walking distance, the Bean was right up the street. Great food spots a few minutes away! The Chicago Riverwalk was right around the corner. Perfect location.

Reviewed on Aug 25, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥425,614
per person
Nov 15 - Nov 20
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

Downtown Chicago
¥518,716
per person
Oct 7 - Oct 13
found 5 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,609 reviews)
The room was just okay. It was advertised (and priced) as luxury but I would not consider this a luxury hotel. It was just an average room. The location was great. We could walk mostly everywhere. The room, beds and shower were really small. I could barely move around in the shower at all. The furniture was a little dated and had several scuff marks. I also wish there was a microwave. All in all, the hotel was fine for what we needed it for and the staff was friendly. But I would not stay here again. It was very expensive for what we got. Not really sure why this is considered a luxury hotel. That’s what happens when you mainly watch reviews from influencers who are paid to stay at the hotel.

Reviewed on Aug 25, 2026

Where to stay in West Englewood

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

West Englewood Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
¥16,977
¥20,185 total
Sep 8 - Sep 9
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
¥21,313
¥25,340 total
Aug 31 - Sep 1
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
¥40,644
¥47,713 total
Sep 18 - Sep 19
includes taxes & fees
8.4/10 Very Good! (2,442 reviews)
"It is located walking distance within the airport"

Reviewed on Aug 25, 2026

Hilton Chicago O'Hare Airport
See all 4,594 properties in West 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.

Frequently asked questions

How much does a West Englewood vacation package cost?
Get ready to book, because a trip to West Englewood starts from just ¥387,655. When you bundle your hotels, flights and car rentals into a travel package, you'll enjoy the best prices.
How do I get a cheap travel package to West Englewood?
Our West Englewood vacation packages offer plenty of savings for the savvy explorer. For the best deal, simply combine your hotel, flights and tours into a handy package. But bargain prices are just the beginning of your next unforgettable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotel options throughout the world to select from. No matter your budget or style, there's a vacation package that's perfect for you.
Where should I stay in West Englewood?
You'll want to stay where the action is. Many visitors favor hotels around top sights, like Marquette Park, St. Bernard Hospital and Balzekas Museum of Lithuanian Culture.
How far in advance should I book my West Englewood vacation?
While prices change from time to time, we generally suggest booking your vacation as soon as possible. Many international fares can be compared on Expedia up to a year in advance. If you're booking late, you may still get lucky. Discount prices to West Englewood sometimes appear only weeks before departure.
What does an Expedia West Englewood travel package include?
With Expedia, you can choose a combination of flights, car rentals and hotels to create your ideal West Englewood travel package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Remember, the more you bundle, the more deals you'll score!
What should I know before booking a West Englewood travel package?
You can save a tidy sum by bundling your airfares, hotels and rental cars. Once you've created your package, you can add on sightseeing tours or experiences. Your next awesome vacation is only a couple of clicks away.
If I'm not able to travel, can I cancel my West Englewood vacation package?
Plans can change suddenly, so yes, you can. You may be able to amend or cancel your West Englewood vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, airline or hotel may charge additional fees. Looking for more information? Take a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.