Essex Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Booked a lake view room and got a partial view. I definitely wouldn’t have payed more if I knew it was partial

Reviewed on 25 Nov 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (931 reviews)
The property was aesthetically pleasing and we received excellent service from the front desk and bellman. I wanted to love this hotel however the refrigerator and the room repeatedly made humming sounds. The mattress was really hard. You could hear the elevators running all hours of the evening while trying to sleep and the air conditioning unit did not work as expected. I did appreciate the location and the staff’s kindness and willingness to help. I’d be willing to stay again with a different room with fewer noises and a more comfortable mattress.

Reviewed on 26 Nov 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Great location next to Millennium Park for kids. Bonus for staying there during holiday ceremonies of tree lighting ceremony, Mag Mile lighting parade, and Chriskindlmarket.

Reviewed on 26 Nov 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.

Reviewed on 20 Nov 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 10 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Great, small hotel in the heart of Chicago, Amazing attention to detail very comfortable room well appointed

Reviewed on 25 Nov 2024

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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 €113 per night from 8 Dec to 9 Dec
€113
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (8,182 reviews)
"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled"

Reviewed on 25 Nov 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €117 per night from 26 Dec to 27 Dec
€117
includes taxes & fees
26 Dec - 27 Dec
8.6/10 Excellent! (3,561 reviews)
"The Hotel needs to get its iwn parking for sure it never stayed we had to walk 2 blocks that was terrible"

Reviewed on 25 Nov 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €108 per night from 26 Dec to 27 Dec
€108
includes taxes & fees
26 Dec - 27 Dec
8.4/10 Very Good! (3,270 reviews)
"The staff are very accommodating in allowing for early luggage drop off before check in and after checking out. Super convenient to local transit and Amtrak Chicago Union Station."

Reviewed on 24 Nov 2024

Club Quarters Hotel, Central Loop, Chicago
See all 3,869 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 €653, 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

4.5/5(14 reviews)

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
McCormick Place

McCormick Place

4.5/5(36 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
Wrigley Field featuring central business district, a city and a sporting event

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

Things to do

Flyover in Chicago

Flyover in Chicago

€35
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

€42
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

€50
Per adult
94% of travellers recommend
Architecture River 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.