South Englewood Vacations from ￥96,893

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest South Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥127,701, price is now ￥96,893 per person
￥96,893
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,270 reviews)
The facilities are old, the room is not clean, the bedding smells of sweat, the pillow also has yellow marks, and there is still the hair of the previous guest on the washstand.

Reviewed on Jul 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥177,007, price is now ￥114,218 per person
￥114,218
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
salty breakfast

Reviewed on Jul 15, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥432,973, price is now ￥334,033 per person
￥334,033
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Staff was fantastic and always ready to help; from the front door to the room door!

Reviewed on Jul 15, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥399,552, price is now ￥309,262 per person
￥309,262
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on Jul 14, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥520,328, price is now ￥420,151 per person
￥420,151
per person
Aug 25 - Aug 29
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very clean nice workers and amazing views

Reviewed on Jul 14, 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
A busy city street with tall buildings, a bus, and cars.

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

South Englewood Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥27,419 per night from Aug 4 to Aug 5
￥27,419
￥31,253 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (2,848 reviews)
"Your security guys are lousy"

Reviewed on Jul 14, 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥26,591 per night from Jul 27 to Jul 28
￥26,591
￥31,616 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,743 reviews)
"Front desk person were very r"

Reviewed on Jul 15, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥38,128 per night from Jul 26 to Jul 27
￥38,128
￥50,731 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,913 reviews)
"Staff was fantastic and always ready to help; from the front door to the room door!"

Reviewed on Jul 15, 2026

Omni Chicago Hotel
See all 4,349 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 ￥96,893, 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,389
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,992
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,502
per adult
92% of travellers recommend
Art Institute of 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.