Englewood Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

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
A busy city street with tall buildings, a bus, and cars.

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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$362 per night from 8 July to 9 July
NZ$362
8 July - 9 July
includes taxes & fees
8.2/10 Very good! (1,689 reviews)
"We like our room, very clean and spacious"

Reviewed on 4 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
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$253 per night from 6 July to 7 July
NZ$253
6 July - 7 July
includes taxes & fees
8/10 Very good! (10,159 reviews)
"Great location- good price for a holiday weekend"

Reviewed on 4 July 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$363 per night from 8 July to 9 July
NZ$363
8 July - 9 July
includes taxes & fees
9.2/10 Wonderful! (1,846 reviews)
"Great staff"

Reviewed on 5 July 2026

Omni Chicago Hotel
See all 4,487 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 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.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$41
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.