Englewood Vacations from ￥293,079

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The Latest Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥399,936, price is now ￥293,079 per person
￥293,079
per person
May 1 - May 6
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was ￥573,705, price is now ￥431,470 per person
￥431,470
per person
Apr 30 - May 6
found 8 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was ￥489,058, price is now ￥391,456 per person
￥391,456
per person
Apr 30 - May 6
found 8 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
The room was so beautiful and spotless. We got housekeeping the whole stay. The staffs were so great and kind to us. Will definitely stay in another Viceroy.

Reviewed on Feb 20, 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was ￥401,074, price is now ￥335,386 per person
￥335,386
per person
Apr 30 - May 6
found 8 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
The room was clean, the staff at check in was great. The lobby amenities were good. Having a water refill station with still and sparkling water was clutch. Location is amazing! Will return.

Reviewed on Feb 17, 2026

Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

3 out of 5
Downtown Chicago
Price was ￥411,156, price is now ￥344,576 per person
￥344,576
per person
Apr 30 - May 6
found 8 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9/10 Wonderful! (1,940 reviews)
Courteous staff, room was clean and comfortable. I would stay there again.

Reviewed on Feb 19, 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 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

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 ￥13,804 per night from Feb 21 to Feb 22
￥13,804
￥16,204 total
Feb 21 - Feb 22
includes taxes & fees
8/10 Very Good! (9,918 reviews)
When you check in they still have plexiglass between you and the front desk clerk - not very welcoming. The hallways and rooms are very dated. But, most important the room was clean and the bed/pillows were comfortable. Probably wouldn't stay here again.

Reviewed on Feb 20, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥15,371 per night from Mar 4 to Mar 5
￥15,371
￥22,418 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,379 reviews)
I had a really great stay at Hotel Riu Plaza Chicago overall. The location was honestly one of the best parts, it’s perfectly situated and close to so many attractions, restaurants, and things to do. Everything I planned during my trip was within easy reach, which made getting around super convenient ...

Reviewed on Feb 20, 2026

Hotel Riu Plaza Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,434 per night from Mar 7 to Mar 8
￥21,434
￥29,702 total
Mar 7 - Mar 8
includes taxes & fees
8.4/10 Very Good! (2,645 reviews)
Bathrooms and furniture was not clean at all. Splatter of dark brown-red substance on lampshade. Bathroom shower grout had similar brown-red stains and hair stuck in tub. Otherwise good. Room was spacious.

Reviewed on Feb 20, 2026

Hilton Chicago
See all 4,808 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 ￥293,079. 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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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
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

Things to do

Art Institute of Chicago

Art Institute of Chicago

￥6,191
per adult
92% of travellers recommend
Art Institute of Chicago
Picture 7 for Activity Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

￥6,810
per adult
98% of travellers recommend
Chicago River: 1.5-Hour Guided Architecture Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,269
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.