Essex Holidays from AU$3,718

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Your Essex Holiday

Make planning your travels easy by snapping up a holiday package to Essex. We'll handle the details, so you can focus on enjoying everything this neighbourhood has to offer. Wondering what to see and do during your trip to Essex? Nearby attractions like University of Chicago, Chicago Museum of Science and Industry and Robie House are good places to start. Stop daydreaming and start doing. When it's time to book your next holiday to Essex, Expedia is here to help.

Top Holiday Package Deals in Essex

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Price was AU$4,210, price is now AU$3,718 per person
AU$3,718
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
8/10 Very Good! (9,398 reviews)
absolutely loved the view from my room on the 14th floor

Reviewed on 23 Oct 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$5,267, price is now AU$4,373 per person
AU$4,373
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
This hotel was nearly perfect! Great staff. Great location. Clean. My only complaint was the ice machine was broken on our floor. We reported it to staff 3 separate occasions and it wasn’t fixed in the 5 days we were there. Hotel is located on a busy street so there is some noise but if that Doesn't bother you… this is perfect. Very walkable location! The staff there are fantastic. From the moment you walk in until the moment you leave. They understand the assignment. Highly recommend.

Reviewed on 21 Oct 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$4,694, price is now AU$3,955 per person
AU$3,955
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on 20 Oct 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was AU$4,512, price is now AU$3,955 per person
AU$3,955
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Everything was amazing. I will definitely be back!

Reviewed on 23 Oct 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$4,597, price is now AU$4,062 per person
AU$4,062
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We had an amazing time staying at the Arlo. The staff was very friendly, the check-in/check-out process was very fast. The room was always clean. The location of the hotel is extremely convenient. Everything was awesome. I’m 100% coming back when I’m in Chicago again.

Reviewed on 22 Oct 2025

Our guide on where to stay in Essex

Find the best Essex areas and neighborhoods for the activities you enjoy most. Learn more about Essex
Downtown Chicago featuring a city

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 Essex 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$169 per night from 24 Nov to 25 Nov
AU$169
24 Nov - 25 Nov
includes taxes & fees
7.8/10 Good! (9,498 reviews)
The website for the gazebo restaurant within the hotel said there was an extensive menu. When you get down to the place it’s a small buffett set up which was similar to any other continental breakfast with some cereal, muffins, fruit, some biscuits, bacon and sausage etc. There was also a man at ...

Reviewed on 20 Oct 2025

Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is AU$250 per night from 23 Nov to 24 Nov
AU$250
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,943 reviews)
Great location if you have meetings at the Mart which you can reach through escalator and a bridge that takes you directly to the second floor. The hotel is well run Good breakfast and friendly staff. Rooms are clean but they should start “refreshing” some of the features like carpets which seem ...

Reviewed on 13 Oct 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 16 Nov to 17 Nov
AU$201
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,133 reviews)
Every think was wonderful except the heater wasn’t working and the toilet was loose.

Reviewed on 19 Oct 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,306 properties in Essex
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 Essex holiday package cost?
Our Essex packages, which begin from just AU$3,718, are an easy way to save money. Pick and choose your favourite hotels, flights and rental car to create a personalised getaway.
How do I get a cheap travel package to Essex?
By bundling. Flights, hotels and rental cars — combine whatever you need into an Essex holiday package to save a pile of cash. Score even more deals when you include extras such as day tours to your booking. But that's not the only good part. You have the flexibility to put together your holiday your own way. We offer more than 550 air carriers and 1 000 000 hotels throughout the world, so that everyone has a chance to travel and fulfil those holiday fantasies.
Where should I stay in Essex?
A holiday in Essex isn't complete without visiting University of Chicago, Chicago Museum of Science and Industry and University of Chicago Medicine. Spend your evenings near these attractions and make sightseeing easy.
How far in advance should I book my Essex holiday?
Reserving your spot early with Expedia means one less thing to worry about. Most air carriers advertise prices up to a year in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Essex are still known to appear a few weeks before departure.
What does an Expedia Essex travel package include?
Expedia has everything you need to lock in Essex escape, but how your package is structured is totally up to you. Pick from any combination of flights, hotels and rental cars. Searching for some tours or activities to keep you on the go? Once you've made your booking, you can add them on too. No matter your style or budget, there's a deal to meet your needs.
What should I know before booking an Essex travel package?
A package can be easier on the wallet than separately booking all you need for your trip. For example, combine your flights, hotels and rental cars and score big savings. No matter your holiday plans, you'll find a package that matches your budget.
Can I choose my airline with an Essex Expedia holiday package?
You sure can. We have more than 550 airline partners across the globe, so pick the carrier that matches your budget needs.
If I'm not able to travel, can I cancel my Essex holiday package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Essex holiday package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more information, browse our Customer Service Portal. We'll help you each step of the way.

Discover the most popular places to visit in Essex

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 showing modern architecture, a city and street scenes

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
Grant Park

Grant Park

4.5/5(47 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

Activities

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.