Englewood Vacations from ￥307,376

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The Latest Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥382,160, price is now ￥307,376 per person
￥307,376
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Great experience and friendly staff

Reviewed on Apr 6, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥446,572, price is now ￥335,170 per person
￥335,170
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The room was clean. Very modern hotel. Great service and staff. Great experience overall.

Reviewed on Apr 7, 2026

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥394,250, price is now ￥312,527 per person
￥312,527
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.

Reviewed on Apr 4, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥404,794, price is now ￥325,539 per person
￥325,539
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
The panoramic room was breathtaking. I came to celebrate my birthday and it was amazing!!!! I HAVE to make my way back soon.

Reviewed on Apr 7, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was ￥411,950, price is now ￥332,051 per person
￥332,051
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on Apr 6, 2026

Where to stay in Englewood

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

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Englewood Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥18,375 per night from Apr 26 to Apr 27
￥18,375
￥21,572 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,052 reviews)
The hotel is very run down and smells as soon as you enter rooms are a great size and clean but very thin walls and you can hear everything called security on first night and took over an hr for someone to come no help at all never got any sleep that night all in all I would not stay here again much ...

Reviewed on Apr 7, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,888 per night from Apr 26 to Apr 27
￥21,888
￥25,694 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,077 reviews)
Didn’t like the bed so much and the couch wasn’t comfy but overall I would stay again

Reviewed on Apr 7, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is ￥24,749 per night from Apr 12 to Apr 13
￥24,749
￥29,054 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,833 reviews)
The pool was small and I felt like it was not clean. Kids couldn’t even see under water with their goggles. There were a lot of kids running around without parents and we had several knocks on our door from kids messing around. We did call down to the front desk and they sent security up immediately. ...

Reviewed on Apr 7, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,791 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.

Frequently asked questions

How much does an Englewood vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Englewood from just ￥307,376. And the more you bundle, the more cash you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Englewood?
Combining your hotel and flight with Expedia won't just save you time — it'll save you a pretty penny too. An Englewood vacation package makes it a breeze to arrange the ideal trip. With more than 550 airlines across the world to pick from, finding convenient flights that suit your schedule won't be difficult. In addition to that, we've got over 1,000,000 hotel options globally to choose from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Where should I stay in Englewood?
With loads to explore in Englewood, it'd be convenient for you to book a hotel near its attractions. St. Bernard Hospital, Holy Cross Hospital and University of Illinois Mile Square Health Center are some interesting ones to put on your to-do list.
How far in advance should I book my Englewood vacation?
While prices change from time to time, we generally recommend booking your vacation as soon as possible. Many international fares are found on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Discount prices to Englewood sometimes occur just weeks before departure.
What does an Expedia Englewood travel package include?
It all depends on what kind of trip you're contemplating. Englewood travel deals can include hotels, car rentals and flights. You can mix and match to find the package that suits your style and budget. You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking an Englewood travel package?
Find deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we have everything you need to plan your escape. You'll save precious cash just by combining your bookings. Whether you're heading away on a ski trip or relaxing on a sunny beach, your dream vacation is just clicks away.
Can I choose my airline with an Englewood Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Englewood vacation package?
Certainly, and we're here to help. You may be able to amend or cancel your Englewood vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans unexpectedly change, visit our Customer Service Portal for more information.

Discover the most popular places to visit in Englewood

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,923 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,285
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,348
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,427
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.