Essex Holidays from £903
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to £750 when you book a flight and hotel together*
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- Rest easyPackages with flights are ATOL protected
Your Essex Holiday
When a break in the city is calling, answer it with a holiday package to Essex. The neighbourhood of Magnificent Mile, which is great for cafes, shopping and history, makes an excellent base for your adventures. Every trip to Essex needs a well-planned itinerary. Fill yours with leading attractions like University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. No matter your travel plans or budget, organising a tailored Essex holiday is a walk in the park with Expedia.
Price found within the past 48 hours. Click for updated prices.
Where to stay in Essex
Find the best Essex areas and neighborhoods for the activities you enjoy most. Learn more about Essex
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Essex
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
£109
2 Nov - 3 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
£142
2 Nov - 3 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£129
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,444 reviews)
"It was way more that i expected, ample rooms, clean and well lighted, and don’t mention the location, it was great experience. 👍"
Reviewed on 9 Oct 2026
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 travel package cost?
Say yes to new adventures with our Essex travel packages, which start from only £903. Choose the hotels and flights that fit your travel plans. Then, add on some sightseeing activities to round off your unique escape.
If I'm not able to travel, can I cancel my Essex travel package?
We totally understand — the universe can throw the odd curveball. If you've booked an Essex travel package and need to amend or cancel it, we're here to help. It's always worth checking out our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary for free. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to Essex?
Just think of all the awesome things you could do in Essex with a pile of extra cash in your wallet. Watch your savings stack up when you bundle your airfare and hotel bookings into an Essex travel package. You have loads of choice when you book your trip with Expedia too. In fact, you can select from more than 550 airlines and 1,000,000 hotel options globally. Whether you're heading off with the entire family or embarking on a solo adventure, exploring Essex is better with a package.
Does Expedia offer Book Now, Pay Later Essex holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a dream getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:
- Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying just a small amount each month works for you, choose this option at checkout.
- Pay in instalments holidays: If you'd like to pay for your escape across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: When you see an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your getaway.
Where should I stay in Essex?
With lots to explore in Essex, we recommend you secure a room in a hotel close to its attractions. University of Chicago, Chicago Museum of Science and Industry and Midway Plaisance are some popular ones to put on your itinerary.
What are the top hotels in Essex?
If it's your first visit to Essex, reserve a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both hotels offer comfy beds and are favourites with lots of travellers.
How far in advance should I book my Essex holiday?
It can be difficult to know exactly when the best time is to book your Essex holiday. But typically the earlier you book, the better the prices. In some cases, you can lock in your flights and hotels nearly a year before your departure date. If you're hoping for a last-minute getaway, no need to worry! There are unbeatable deals announced on Expedia every single day.
What does an Expedia Essex travel package include?
That depends on what you're after. If you're travelling solo, you might decide to combine flights and hotels. Taking the whole family to Essex? A travel package including hotels, rental cars and flights might be a better fit. Expedia gives you the flexibility and freedom to build your own travel package.
What should I know before booking an Essex travel package?
Bundling your bookings into an Essex travel package is the easiest way to organise your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with an Essex Expedia travel package?
With a travel package, the choice is in your hands. Whether you'd like to fly to Essex in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 airline partners globally.
Things to do
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.