Essex Holidays

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    Save up to NZ$616 when you book a flight and hotel together*

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

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Save up to 40% on select hotels
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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

4 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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$260 per night from 21 Dec to 22 Dec
NZ$260
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (2,073 reviews)
Staff could not have been more helpful. The venue was packed for an international rugby game, but everything was clean, well cared for and comfortable. Will defintiely stay here again!

Reviewed on 18 Nov 2025

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 21 Dec to 22 Dec
NZ$182
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (5,271 reviews)
Great location. Fantastic staff. Breakfast was absolutely amazing. Only issue we had was insufficient bath towels and front desk resolved this quickly. I would gladly stay here again without a doubt

Reviewed on 18 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
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 NZ$175 per night from 7 Dec to 8 Dec
NZ$175
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,335 reviews)
Friendly staff, clean rooms

Reviewed on 19 Nov 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,372 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.

Frequently asked questions

How much does an Essex holiday package cost?
Our Essex packages, which begin from just , 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

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Relax and enjoy the view

Chicago Architecture Center River Cruise aboard First Lady

NZ$97
per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
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.