South Englewood Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 14 - Aug 19

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.2/10 - Very good (2,778 reviews)
    "Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable."
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,755
    NZ$3,018
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Terrace/patio
    Aug 14 - Aug 19

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,888 reviews)
    "Great job"
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$5,787
    NZ$4,480
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Smart TV
    Aug 14 - Aug 19

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,504
    NZ$3,493
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Lobby
    Aug 14 - Aug 19

    The Langham, Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,007 reviews)
    "The pool was a true lap pool. The Fitness Center and the locker room was exquisite."
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$6,321
    NZ$4,955
    per traveller
    found 1 day ago
    The Langham, Chicago
  • Breakfast and dinner served
    Aug 14 - Aug 19

    Omni Chicago Hotel + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (1,800 reviews)
    "Old hotel and rooms. All the outlets in our room were titled and so hard to plug things in them. The outlets near the nightstands on either sides can’t accommodate a charger because they’re stuck on the side of the nightstand between it and the side of the bed. Hairdryer so old and didn’t work. Check in was exactly at 4, they weren’t lenient when I showed up at 2:40."
    Reviewed June 10, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,997
    NZ$3,250
    per traveller
    found 1 day ago
    Omni Chicago Hotel

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 NZ$278 per night from 29 June to 30 June
NZ$278
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,236 reviews)
"First, this is a historic hotel, and visitors should be aware that the rooms reflect the historic vibe. If you want modern, you need to stay down the street at the Hilton. The rooms were very cute and clean, and the tiling in the bathroom was beautiful. The hotel has a prime location with easy walking ..."

Reviewed on 10 June 2026

Congress Plaza Hotel
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 NZ$312 per night from 28 June to 29 June
NZ$312
28 June - 29 June
includes taxes & fees
8.8/10 Excellent! (2,641 reviews)
"The door to the restroom kept getting jammed and wouldn’t close properly. Our room also had no WiFi… the staff couldn’t figure out why it wasn’t working."

Reviewed on 10 June 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is NZ$327 per night from 1 July to 2 July
NZ$327
1 July - 2 July
includes taxes & fees
7.8/10 Good! (1,550 reviews)
"The hotel was amazing, the room was clean and big, the only bad thing was the check in… your employees are rude and disgusting… The girl from the breakfast and the guy from the rooftop were nice and respectful, we really like them"

Reviewed on 9 June 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,543 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 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

Wrigley Field

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
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)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

NZ$68
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.