Englewood Vacations

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  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Aug 19 - Aug 20

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    1 night
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Roundtrip • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Nonstop ORD - LAX • Nonstop
    ₩826,735
    ₩714,501
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • Front of property
    Aug 23 - Aug 27

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (4,405 reviews)
    "It was wonderful, clean rooms, quick staff. HUGE breakfast area. Beautiful rooftop bar and grill. Staff were very compassionate and helpful when I got injured on my last day there too!"
    Reviewed June 10, 2026
    Roundtrip • Seoul (ICN) - Chicago (ORD)
    ICN - ORD • 1 stop ORD - ICN • 1 stop
    ₩3,583,170
    ₩2,936,802
    per traveler
    found 5 hours ago
    Hotel Riu Plaza Chicago
  • Exterior detail
    Aug 23 - Aug 27

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,327 reviews)
    "Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on. The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful. Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the..."
    Reviewed June 8, 2026
    Roundtrip • Seoul (ICN) - Chicago (ORD)
    ICN - ORD • 1 stop ORD - ICN • 1 stop
    ₩3,879,552
    ₩3,265,908
    per traveler
    found 5 hours ago
    The Emily Hotel
  • Indoor pool, open 6:00 AM to 9:00 PM, sun loungers
    Aug 24 - Aug 28

    Nobu Hotel Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.4/10 - Exceptional (866 reviews)
    "Fabulous walkable neighborhood. Roo.s are spacious and very nicely designed"
    Reviewed June 10, 2026
    Roundtrip • Seoul (ICN) - Chicago (ORD)
    ICN - ORD • 1 stop ORD - ICN • 1 stop
    ₩4,467,538
    ₩3,843,841
    per traveler
    found 2 hours ago
    Nobu Hotel Chicago
  • Terrace/patio
    Aug 23 - Aug 27

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

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,535 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Roundtrip • Seoul (ICN) - Chicago (ORD)
    ICN - ORD • 1 stop ORD - ICN • 1 stop
    ₩3,658,528
    ₩3,156,549
    per traveler
    found 5 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

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

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 ₩207,606 per night from Jun 29 to Jun 30
₩207,606
₩246,826 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,237 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 Jun 10, 2026

Congress Plaza Hotel
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 ₩243,769 per night from Jul 1 to Jul 2
₩243,769
₩289,817 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,551 reviews)
"Enjoyed our stay"

Reviewed on Jun 10, 2026

The Chicago Hotel Collection - Magnificent Mile
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 ₩243,408 per night from Jun 28 to Jun 29
₩243,408
₩277,437 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,644 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 Jun 10, 2026

Hyatt Regency O'Hare Chicago
See all 4,632 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.

Frequently asked questions

How much does an Englewood vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Englewood from just . And the more you bundle, the more cash you save. Your dream vacation 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 vacation 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 Center are some interesting ones to put on your to-do list.
How far in advance should I book my Englewood vacation?
While prices change from time to time, we generally recommend booking your vacation 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 vacation is just clicks away.
Can I choose my airline with an Englewood Expedia vacation 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 vacation package?
Certainly, and we're here to help. You may be able to amend or cancel your Englewood vacation 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

Navy Pier

Navy Pier

4.5/5(4,925 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park

Millennium Park

4.5/5(7,309 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

4.5/5(3,360 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.