Essex Holidays from AU$3,052

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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.
LakeWood Inn & Suites

LakeWood Inn & Suites

2 out of 5
Price was AU$3,140, price is now AU$3,052 per person
AU$3,052
per person
2 July - 8 July
found 19 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
7.2/10 Good! (73 reviews)
Property was nice...exactly what i expected...beds were great..slept like a baby

Reviewed on 20 Oct 2025

The Morris Estate

The Morris Estate

4 out of 5
Price was AU$4,651, price is now AU$4,107 per person
AU$4,107
per person
2 July - 8 July
found 19 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
10/10 Exceptional! (128 reviews)
Had a great stay! Great place!

Reviewed on 4 May 2026

The Brewery Lodge Hotel

The Brewery Lodge Hotel

3.5 out of 5
Price was AU$3,852, price is now AU$3,593 per person
AU$3,593
per person
2 July - 8 July
found 19 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (831 reviews)
Everything was great other than the bed being super hard. It felt cozy like I was staying at someone’s grandmas house.

Reviewed on 11 May 2026

Holiday Inn Express Hotel & Suites Niles by IHG

Holiday Inn Express Hotel & Suites Niles by IHG

2.5 out of 5
Price was AU$3,684, price is now AU$3,526 per person
AU$3,526
per person
2 July - 8 July
found 19 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (749 reviews)
Staff and breakfast was great.

Reviewed on 27 Apr 2026

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

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
The price is AU$219 per night from 26 May to 27 May
AU$219
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.

Reviewed on 12 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$272 per night from 25 May to 26 May
AU$272
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,128 reviews)
Breakfast was good.

Reviewed on 13 May 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is AU$214 per night from 25 May to 26 May
AU$214
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,285 reviews)
Valet and bellmen were great as always. Polite and helpful. The staff brought up an extra valet for my kids on the pullout couch. Great setup for family with kids! And the restaurant on the corner has the best coffee. We stay here every time we visit, can’t beat location, price and separate space ...

Reviewed on 13 May 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,337 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$3,052, 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

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
Millennium Park

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
88% 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$56
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.