Essex Holidays from £1,216

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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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £1,625, price is now £1,216 per person
£1,216
per person
11 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
Hats off to the doorman ! Go Ghana ! Also beautiful person who checked us in !

Reviewed on 10 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,035, price is now £1,325 per person
£1,325
per person
11 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on 9 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,852, price is now £1,238 per person
£1,238
per person
11 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on 8 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,890, price is now £1,386 per person
£1,386
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on 8 Jul 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,928, price is now £1,446 per person
£1,446
per person
11 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,251 reviews)
Viceroy staff were

Reviewed on 7 Jul 2026

Where to stay in Essex

Find the best Essex areas and neighborhoods for the activities you enjoy most. Learn more about Essex
A busy city street with tall buildings, a bus, and cars.

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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £209 per night from 9 Aug to 10 Aug
£209
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,895 reviews)
"Unfortunately I didn't have the best experience. I am giving them an okay review because they did attempt to make it right. Without the check out employee in the morning; i probably would have gave this a very poor experience. He did take off the resort fee of $35ish & my $18 breakfast. When I arrived; ..."

Reviewed on 10 Jul 2026

Omni Chicago Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 27 Jul to 28 Jul
£136
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,727 reviews)
"Great place in a great location. Restaurant and breakfast buffet were excellent."

Reviewed on 10 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 £168 per night from 10 Aug to 11 Aug
£168
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,218 reviews)
"Our stay was great, best was comfortable and room was clean."

Reviewed on 9 Jul 2026

Congress Plaza Hotel
See all 4,124 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 £1,216. 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£31
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.