Englewood Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Meeting facility
    Jul 28 - Aug 4

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.2/10 - Wonderful (1,367 reviews)
    "Excellent hotel and close to restaurants and shopping. Very clean."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,948
    AU$3,786
    per traveller
    found 13 hours ago
    Thompson Chicago, by Hyatt
  • Indoor wedding
    Jul 28 - Aug 4

    Swissotel - Chicago + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.0/10 - Wonderful (3,341 reviews)
    "Really a great hotel. The view was amazing from our room. The room was large and lots of space to hang out. The bed was comfy, and so were the pillows."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    Save 100% on your flight
    AU$6,123
    AU$3,882
    per traveller
    found 13 hours ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 28 - Aug 4

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,511 reviews)
    "Walls are paper thin. We literally heard snoring all night from the room next to us. Also, the smell of cigarette smoke kept coming into our room. Rooms were nice and clean. The view was 🔥."
    Reviewed May 23, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$5,762
    AU$4,025
    per traveller
    found 13 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 28 - Aug 4

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.4/10 - Exceptional (3,725 reviews)
    "Super location, good crowd of staff and fellow travellers. Smells great!"
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$6,045
    AU$4,257
    per traveller
    found 13 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Executive lounge
    Jul 28 - Aug 4

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    8.8/10 - Excellent (2,166 reviews)
    "Perfect location to sight see Chicago. Staff were not friendly and when I asked a question felt like it was too much effort for them to respond in a professional helpful manner. Saying that the hotel was beautiful and the rooms were perfect. Great view."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$5,126
    AU$3,886
    per traveller
    found 13 hours ago
    Fairmont Chicago at Millennium Park

Our guide on where to stay in Englewood

Find the best Englewood areas and neighborhoods for the activities you enjoy most. Learn more about 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 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 26 May to 27 May
AU$223
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,138 reviews)
"Good"

Reviewed on 25 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$439 per night from 16 June to 17 June
AU$439
16 June - 17 June
includes taxes & fees
9.4/10 Exceptional! (4,238 reviews)
"Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk."

Reviewed on 25 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$266 per night from 27 May to 28 May
AU$266
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,467 reviews)
"Complimentary breakfast was really nice."

Reviewed on 24 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,721 properties in 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 an Englewood holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Englewood from just . And the more you bundle, the more cash you save. Your dream holiday has never been more affordable.
How do I get a cheap travel package to Englewood?
Combining your hotel and flight with Expedia won't just save you time — it'll save you a pretty penny too. An Englewood holiday package makes it a breeze to arrange the ideal trip. With more than 550 airlines across the world to pick from, finding convenient flights that suit your schedule won't be difficult. In addition to that, we've got over 1 000 000 hotel options globally to choose from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Where should I stay in Englewood?
With loads to explore in Englewood, it'd be convenient for you to book a hotel near its attractions. St. Bernard Hospital, Holy Cross Hospital and University of Illinois Mile Square Health Centre are some interesting ones to put on your to-do list.
How far in advance should I book my Englewood holiday?
While prices change from time to time, we generally recommend booking your holiday as soon as possible. Many international fares are found on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Discount prices to Englewood sometimes occur just weeks before departure.
What does an Expedia Englewood travel package include?
It all depends on what kind of trip you're contemplating. Englewood travel deals can include hotels, car rentals and flights. You can mix and match to find the package that suits your style and budget. You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking an Englewood travel package?
Find deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we have everything you need to plan your escape. You'll save precious cash just by combining your bookings. Whether you're heading away on a ski trip or relaxing on a sunny beach, your dream holiday is just clicks away.
Can I choose my airline with an Englewood Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Englewood holiday package?
Certainly, and we're here to help. You may be able to amend or cancel your Englewood holiday package at no cost if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans unexpectedly change, visit our Customer Service Portal for more information.

Discover the most popular places to visit in 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

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

Navy Pier
Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

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
Art Institute of Chicago

Art Institute of Chicago

AU$55
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.