South Englewood Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jun 24 - Jun 28

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,371
    AU$3,762
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jun 24 - Jun 28

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (1,878 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,435
    AU$4,637
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Seasonal outdoor pool, pool loungers
    Jun 24 - Jun 28

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,231 reviews)
    "We had an incredible stay here. The room was very nice as we stayed in a junior suite so the extra charge was definitely worth it. You’re on the 17th floor and you’re able to have a good view of the city. You also are one floor away from the rooftop restaurant and bar. The decor and aesthetics in the hotel are top-notch. Definitely picture worthy. Definitely walkable and it’s less than quarter mile from the hotel to the lake. 10 out of 10 definitely recommend."
    Reviewed May 23, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,114
    AU$4,381
    per traveller
    found 1 day ago
    Viceroy Chicago
  • 2 restaurants; breakfast, lunch, and dinner served
    Jun 24 - Jun 28

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,721 reviews)
    "Great location!"
    Reviewed May 22, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,627
    AU$3,997
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Meeting facility
    Jun 24 - Jun 28

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,366 reviews)
    "Great location"
    Reviewed May 19, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,788
    AU$4,193
    per traveller
    found 1 day ago
    Thompson Chicago, by Hyatt

Our guide on 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

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

Our pick of the best 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 AU$223 per night from 25 May to 26 May
AU$223
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,134 reviews)
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."

Reviewed on 23 May 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 AU$387 per night from 26 May to 27 May
AU$387
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (4,221 reviews)
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."

Reviewed on 24 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is AU$203 per night from 26 May to 27 May
AU$203
26 May - 27 May
includes taxes & fees
7.8/10 Good! (1,464 reviews)
"There're bed bugs. Be careful"

Reviewed on 24 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,580 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.
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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 1 000 000 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.

Discover the most popular places to visit in South Englewood

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$34
per adult
88% 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.