Essex Holidays from £950

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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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
12 Sept - 19 Sept
found 9 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (211 reviews)
Fabulous stay in lovely apartments with great amenities.. can be noisy as expected in a city but almost on top of a railway line

Reviewed on 15 Jun 2025

Art Villa

Art Villa

5 out of 5
West Town
per person
4 Sept - 7 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
No reviews
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
per person
12 Sept - 19 Sept
found 13 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (251 reviews)
The hotel is nice and located in a great area. It’s within walking distance to several points of interest. The staff were friendly and helpful. I really enjoyed my stay.

Reviewed on 13 May 2025

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
per person
12 Sept - 19 Sept
found 13 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very Good! (1,635 reviews)
Nice and comfortable. Great price!

Reviewed on 26 Jun 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 featuring 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 £140 per night from 29 Jun to 30 Jun
£140
29 Jun - 30 Jun
includes taxes & fees
8.4/10 Very Good! (4,279 reviews)
"Perfect property, everything is walkable distance"

Reviewed on 26 Jun 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £157 per night from 1 Jul to 2 Jul
£157
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,921 reviews)
"We especially loved the room service, but the best was the unique indoor pool!!"

Reviewed on 25 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
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 £116 per night from 6 Jul to 7 Jul
£116
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,327 reviews)
"My daughter and I had a great time. The only thing we did like is that the pool was out of service and construction being done."

Reviewed on 24 Jun 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,165 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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 £950. 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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
Magnificent Mile - River North which includes 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

Things to do

River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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. Flight-inclusive packages are ATOL protected.