Essex Holidays from £1,077

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,537, price is now £1,077 per person
£1,077
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
This was a great price for a great stay!! Central to many locations downtown! I am planning to book this hotel again in the future!

Reviewed on 9 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,898, price is now £1,243 per person
£1,243
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great service, loved this place.

Reviewed on 9 Apr 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,789, price is now £1,226 per person
£1,226
per person
17 Jun - 21 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Breakfast was very good. Enjoyed our room and how everything was clean. There was no microwave so don’t try to bring food if you need to reheat it. Fridge was also not strong to freeze my ice cream so be aware. All the staff were kind and helpful. Rooftop was beautiful but the glass floor was out of service. The hotel was close to Michigan Ave so heading to stores was a breeze. Overall, had an amazing time with my partner and would recommend reserving a room at this establishment.

Reviewed on 10 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was £1,964, price is now £1,357 per person
£1,357
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on 6 Apr 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,725, price is now £1,224 per person
£1,224
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Excellent accommodations. Highly recommend.

Reviewed on 9 Apr 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 £101 per night from 26 Apr to 27 Apr
£101
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,077 reviews)
Room was clean, but cheaply remodeled and nothing really special.

Reviewed on 9 Apr 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 £120 per night from 26 Apr to 27 Apr
£120
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,093 reviews)
It was nice

Reviewed on 10 Apr 2026

Hilton Chicago/Magnificent Mile Suites
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 £136 per night from 12 Apr to 13 Apr
£136
12 Apr - 13 Apr
includes taxes & fees
8.6/10 Excellent! (5,832 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on 9 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,419 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.
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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 £1,077. 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

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

£29
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago

Explore a world of travel with Expedia

* 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.