Essex Holidays

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    Save up to €900 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,548, price is now €1,250 per person
€1,250
per person
16 Aug - 21 Aug
found 24 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.

Reviewed on 19 Jun 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €2,048, price is now €1,526 per person
€1,526
per person
16 Aug - 21 Aug
found 24 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Close to a ton of great dining options. Nice staff

Reviewed on 20 Jun 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,894, price is now €1,435 per person
€1,435
per person
16 Aug - 21 Aug
found 24 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.

Reviewed on 20 Jun 2026

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 €1,743, price is now €1,414 per person
€1,414
per person
16 Aug - 21 Aug
found 24 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Usually this is one of the best property but this time they had water pipe burst and elevators werent working because of that. It was very inconvinient for this stay.

Reviewed on 20 Jun 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was €1,668, price is now €1,354 per person
€1,354
per person
16 Aug - 21 Aug
found 24 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
very clean and friendly staff

Reviewed on 18 Jun 2026

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

Top hotels in Essex

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 €141 per night from 29 Jun to 30 Jun
€141
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,150 reviews)
"No hot water. Room was outdated"

Reviewed on 21 Jun 2026

Congress Plaza Hotel
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 €162 per night from 5 Jul to 6 Jul
€162
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (4,452 reviews)
"Clean room exelent"

Reviewed on 19 Jun 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is €134 per night from 30 Jun to 1 Jul
€134
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (1,601 reviews)
"Our stay was amazing! Staff was very helpful!"

Reviewed on 19 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,305 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 €1,250, 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

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
A coastal cityscape with high-rise buildings, a marina, and a park area.

Naval Base Great Lakes

5/5(1 review)

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

4/5(127 reviews)

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€34
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.