Essex Holidays

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  • Better together

    Save up to €185 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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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €912, price is now €632 per person
€632
per person
1 Feb - 6 Feb
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
great staff...loved our stay.

Reviewed on 22 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,522, price is now €1,023 per person
€1,023
per person
1 Feb - 6 Feb
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.

Reviewed on 1 Dec 2025

Chicago luxury home suites

Chicago luxury home suites

2 out of 5
Downtown Chicago
Price was €2,992, price is now €2,082 per person
€2,082
per person
1 Feb - 6 Feb
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.

Reviewed on 26 Nov 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was €969, price is now €680 per person
€680
per person
1 Feb - 6 Feb
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on 26 Nov 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €955, price is now €717 per person
€717
per person
1 Feb - 6 Feb
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
the bellhop and staff were extremely courteous, there was a problem with a transaction and the front staff was immediate at amending the issue. best place i’ve stayed! extremely classy and polite.

Reviewed on 1 Dec 2025

Where to stay in Essex

Find the best Essex areas and neighborhoods for the activities you enjoy most. Learn more about Essex
Downtown Chicago which includes 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

Top hotels in Essex

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 €93 per night from 7 Dec to 8 Dec
€93
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (5,334 reviews)
The location is great! We had to leave a couple hours into our stay due to a major snowstorm so my feedback is limited. We weren’t able to enjoy the breakfast this time but it was fantastic last time we were there. The room was very clean and staff were extremely helpful. I received a text asking ...

Reviewed on 30 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 €84 per night from 7 Dec to 8 Dec
€84
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,388 reviews)
.

Reviewed on 26 Nov 2025

Hilton Chicago/Magnificent Mile Suites
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 €129 per night from 28 Dec to 29 Dec
€129
28 Dec - 29 Dec
includes taxes & fees
8.4/10 Very Good! (2,111 reviews)
Absolutely gorgeous! This hotel offers everything you need and want. Excellent food, amenities and the spa is the best part. We had a mother and daughter weekend with massage's, it was what we hoped for and more.

Reviewed on 29 Nov 2025

Palmer House a Hilton Hotel
See all 4,440 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 €632, 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.

Popular places to visit

Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier

Things to do

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€39
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.