South Englewood Vacations from ￥271,302

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest South Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥366,576, price is now ￥271,302 per person
￥271,302
per person
May 14 - May 19
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
Room was very clean would return again

Reviewed on Feb 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥464,248, price is now ￥345,770 per person
￥345,770
per person
May 1 - May 5
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!

Reviewed on Feb 27, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was ￥396,305, price is now ￥310,066 per person
￥310,066
per person
May 14 - May 19
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,266 reviews)
I stayed here since we had a really good experience with the Thompson in Madrid. This hotel is definitely not in the same star ranking as the one in Madrid. The rooms felt dated and dingy.

Reviewed on Feb 24, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥423,360, price is now ￥352,078 per person
￥352,078
per person
May 1 - May 5
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Always the best place to stay downtown. Central to everything with a great staff. Highly recommend!

Reviewed on Feb 25, 2026

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was ￥368,590, price is now ￥314,658 per person
￥314,658
per person
May 14 - May 19
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,059 reviews)
The check-in staff was really nice. He offered an upgrade for $40/night. It was an awesome upgrade with 2 bathrooms and twice bigger than our original room. The hotel was also really close to the PH Consulate, which was the main reason of this travel. Whole place was clean and everyone was really nice.

Reviewed on Feb 24, 2026

Where to stay in South Englewood

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

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.

Find hotels in Downtown Chicago

South 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 ￥14,468 per night from Feb 28 to Mar 1
￥14,468
￥16,985 total
Feb 28 - Mar 1
includes taxes & fees
8/10 Very Good! (9,892 reviews)
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...

Reviewed on Feb 27, 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 ￥17,608 per night from Mar 4 to Mar 5
￥17,608
￥25,063 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,421 reviews)
Great service

Reviewed on Feb 27, 2026

Hotel Riu Plaza Chicago
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 ￥17,582 per night from Mar 2 to Mar 3
￥17,582
￥20,639 total
Mar 2 - Mar 3
includes taxes & fees
8.6/10 Excellent! (5,692 reviews)
Hotel is beautiful and located in the heart of everything. Starbucks outside is a plus. Breakfast is excellent and rooms are spacious. Wish they have a whirlpool

Reviewed on Feb 27, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,677 properties in South 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 South Englewood vacation package cost?
Our South Englewood packages, which start at just ￥271,302, are an ideal way to save big bucks. All you have to do is choose your preferred hotels, flights and more to create a customized itinerary.
How do I get a cheap travel package to South Englewood?
Bundle your flights and hotels with Expedia to save big on your next big adventure. With over 550 air carriers and 1,000,000 properties across the globe, your South Englewood vacation package can be customized exactly to suit your budget. With all those extra dollars, why not add one or two fun experiences and tours? It's an easy way to unlock even more savings. Your dream vacation in South Englewood is much closer than you thought!
Where should I stay in South Englewood?
A vacation in South Englewood wouldn't be complete without visiting Highland Community Bank, Carter G. Woodson Library and Final Call Newspaper Headquarters. Spend your nights near these top sights and make sightseeing a breeze.
How far in advance should I book my South Englewood vacation?
It all depends on the air carrier, but you can usually compare international fares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky travelers will sometimes score a cheaper flight just weeks before their intended journey.
What does an Expedia South Englewood travel package include?
That depends entirely on you. You can select from a variety of South Englewood packages, such as a rental car, hotel and flight. You can also book a hotel and a flight, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your ideal South Englewood getaway looks like, you're sure to save!
What should I know before booking a South Englewood travel package?
When you book your flights, hotels and car rentals together, you'll walk away with incredible discounts. Whether you're planning an island getaway in a villa or prefer to stay in a fancy hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a South Englewood Expedia vacation package?
Yes, you sure can. We have more than 550 airline partners throughout the world, so select the carrier that suits your travel needs.
If I'm not able to travel, can I cancel my South Englewood vacation package?
Plans can change without warning, so yes. You may be able to cancel and rebook your South Englewood vacation package at no cost if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your car rental company, airline or hotel may charge additional fees. Want more information? Look up our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in South Englewood

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

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

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

Navy Pier

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,810
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,191
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

￥5,885
per adult
98% of travellers recommend
Flyover in Chicago
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.