Englewood Vacations from ￥206,246

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Englewood Vacation Packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,749 reviews)
Beautiful room and a great location! Would definitely recommend!

Reviewed on Jun 19, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,609 reviews)
Beautiful spacious well thought room with no dust, beautiful views of the lake and river and buildings, perfect staff teams (front desk, bellboys, housekeeper team)! I will be back at the same room!

Reviewed on Jun 19, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The customer service was top notch, everyone went above and beyond to make my stay an exceptional experience!! 5 Stars All around!!

Reviewed on Jun 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful property. Amazing customer service.

Reviewed on Jun 17, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Jul 23 - Jul 28
found 13 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (2,008 reviews)
Nice addition to the chicago hotel landscape. Convenient to everything and the Lake! Bed comfortable as well. Love their sustainable touches recycling as well as compost! My only large complaint is they charge the 28$ fee on top of “ all inclusive pricing” and that’s for items that used to be included at any hotel—WiFi, gym, water bottles. Frustrating.

Reviewed on Jun 19, 2025

Where to stay in Englewood

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

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

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
Fully refundableReserve now, pay when you stay
The price is ￥23,316 per night from Jun 30 to Jul 1
￥23,316
￥27,372 total
Jun 30 - Jul 1
includes taxes & fees
8.4/10 Very Good! (4,238 reviews)
"Super friendly and helpful staff!"

Reviewed on Jun 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ￥24,879 per night from Jul 6 to Jul 7
￥24,879
￥33,862 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,891 reviews)
"Hotel is very clean with friendly staff. The pool was a highlight for the kids! Convenient location."

Reviewed on Jun 19, 2025

InterContinental Chicago Magnificent Mile by IHG
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 ￥19,597 per night from Jul 6 to Jul 7
￥19,597
￥23,005 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,314 reviews)
"The staff was incredible! The Chapel Cafe downstairs that is connected to the hotel is absolutely phenomenal! I loved that everything was within walking distance from the hotel including the Riverwalk and the Navy Pier!!! The room was spacious and clean and the total price of the stay was affordable! ..."

Reviewed on Jun 19, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,521 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 ￥206,246. 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 featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,052
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,507
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,499
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.