Essex Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Save up to £750 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages 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.
  • Indoor wedding
    Jul 7 - Jul 12

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,341 reviews)
    "Really a great hotel. The view was amazing from our room. The room was large and lots of space to hang out. The bed was comfy, and so were the pillows."
    Reviewed May 24, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,126
    £767
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Smart TV
    Jul 7 - Jul 12

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    Save 100% on your flight
    £1,339
    £890
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jul 7 - Jul 12

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,511 reviews)
    "Walls are paper thin. We literally heard snoring all night from the room next to us. Also, the smell of cigarette smoke kept coming into our room. Rooms were nice and clean. The view was 🔥."
    Reviewed May 23, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,427
    £1,009
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Executive lounge
    Jul 7 - Jul 12

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.8/10 - Excellent (2,166 reviews)
    "Perfect location to sight see Chicago. Staff were not friendly and when I asked a question felt like it was too much effort for them to respond in a professional helpful manner. Saying that the hotel was beautiful and the rooms were perfect. Great view."
    Reviewed May 24, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,113
    £810
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park
  • Lobby
    Jul 7 - Jul 12

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.2/10 - Very good (2,721 reviews)
    "Great location and helpful staff. Small rooms and public areas."
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,087
    £796
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile

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 £118 per night from 26 May to 27 May
£118
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,138 reviews)
"Good"

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £233 per night from 16 Jun to 17 Jun
£233
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,238 reviews)
"Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk."

Reviewed on 25 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £107 per night from 27 May to 28 May
£107
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,467 reviews)
"Complimentary breakfast was really nice."

Reviewed on 24 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,365 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 . 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
Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
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.