South Englewood Holidays

Book a Hotel + Flight or Car together to unlock savings

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 featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in South Englewood

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.639.942 ₫ per night from 24 Jan to 25 Jan
3.639.942 ₫
5.043.835 ₫ total
24 Jan - 25 Jan
includes taxes & fees
8.4/10 Very Good! (2,502 reviews)
Yes

Reviewed on 7 Jan 2026

Hilton Chicago
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 2.347.655 ₫ per night from 8 Feb to 9 Feb
2.347.655 ₫
2.755.914 ₫ total
8 Feb - 9 Feb
includes taxes & fees
8.8/10 Excellent! (3,707 reviews)
It was a minus 6 outside temperature did not really run the ac

Reviewed on 12 Jan 2026

Hilton Chicago/Magnificent Mile Suites
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.143.306 ₫ per night from 26 Jan to 27 Jan
2.143.306 ₫
2.516.027 ₫ total
26 Jan - 27 Jan
includes taxes & fees
8.6/10 Excellent! (2,056 reviews)
Super fast and easy check in / out experience, amazing location and very affordable

Reviewed on 11 Jan 2026

Club Quarters Hotel Wacker at Michigan, Chicago
See all 4,682 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 holiday package cost?
Our South Englewood packages, which start at just , 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 1null000null000 properties across the globe, your South Englewood holiday 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 holiday in South Englewood is much closer than you thought!
Where should I stay in South Englewood?
A holiday 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 holiday?
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 travellers 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 holiday 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 holiday package?
Plans can change without warning, so yes. You may be able to cancel and rebook your South Englewood holiday 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

McCormick Place
Soldier Field which includes a high-rise building, a city and modern architecture

Soldier Field

4/5(44 reviews)

Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Soldier Field