Essex Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 14 - Jul 26

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    12 nights
    4.0 star property
    8.2/10 - Very good (2,776 reviews)
    "Checking in and out is very smooth. Building is definitely older and although it has been renovated the age shows. The cleanliness of the room was fine, not terrible but not great. Location is great; in a quieter part of the city right near the hustle and bustle. It is right near public transport options."
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$7,339
    NZ$5,025
    per traveller
    found 20 hours ago
    Hotel Felix River North/Magnificent Mile
  • Smart TV
    Jul 14 - Jul 26

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    12 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    Save 100% on your flight
    NZ$8,374
    NZ$5,408
    per traveller
    found 20 hours ago
    Level Chicago Fulton Market
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 14 - Jul 26

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    12 nights
    4.5 star property
    9.4/10 - Exceptional (3,735 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    Save 100% on your flight
    NZ$10,218
    NZ$6,821
    per traveller
    found 20 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 14 - Jul 26

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

    Downtown Chicago
    12 nights
    4.0 star property
    9.4/10 - Exceptional (2,532 reviews)
    "WONDERFUL HOTEL"
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    Save 100% on your flight
    NZ$7,904
    NZ$5,443
    per traveller
    found 20 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Breakfast and dinner served
    Jul 14 - Jul 26

    Omni Chicago Hotel + Flight

    Downtown Chicago
    12 nights
    4.5 star property
    9.2/10 - Wonderful (1,796 reviews)
    "I requested an early check-in during a busy season, and they did their best to accommodate me! The check-in and check-out processes went smoothly, and all the staff are honestly so pleasant. I will definitely be back!"
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$7,911
    NZ$5,558
    per traveller
    found 20 hours ago
    Omni Chicago Hotel

Our guide on 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

Our pick of the best Essex Hotel Deals

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 NZ$279 per night from 29 June to 30 June
NZ$279
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,213 reviews)
"The only redeeming quality of this hotel is the location. For the price it is NOT worth it. The bed is a rock that doesn't even have a fitted sheet on it and did not come with adequate blankets. The AC works well, but with the thin blankets it was almost unbearable. And oh man, the bathroom! Severely ..."

Reviewed on 8 June 2026

Congress Plaza Hotel
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 NZ$312 per night from 28 June to 29 June
NZ$312
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,541 reviews)
"Elevator is very slow, showers are tiny"

Reviewed on 8 June 2026

The Chicago Hotel Collection - Magnificent Mile
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 NZ$338 per night from 29 June to 30 June
NZ$338
29 June - 30 June
includes taxes & fees
8.2/10 Very Good! (1,566 reviews)
"We just stayed one night but the hotel served its purpose. We would stay here again. We also liked the lobby of the hotel and bar"

Reviewed on 8 June 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,270 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.

Frequently asked questions

How much does an Essex holiday package cost?
Our Essex packages, which begin from just , are an easy way to save money. Pick and choose your favourite hotels, flights and rental car to create a personalised getaway.
How do I get a cheap travel package to Essex?
By bundling. Flights, hotels and rental cars — combine whatever you need into an Essex holiday package to save a pile of cash. Score even more deals when you include extras such as day tours to your booking. But that's not the only good part. You have the flexibility to put together your holiday your own way. We offer more than 550 air carriers and 1 000 000 hotels throughout the world, so that everyone has a chance to travel and fulfil those holiday fantasies.
Where should I stay in Essex?
A holiday in Essex isn't complete without visiting University of Chicago, Chicago Museum of Science and Industry and University of Chicago Medicine. Spend your evenings near these attractions and make sightseeing easy.
How far in advance should I book my Essex holiday?
Reserving your spot early with Expedia means one less thing to worry about. Most air carriers advertise prices up to a year in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Essex are still known to appear a few weeks before departure.
What does an Expedia Essex travel package include?
Expedia has everything you need to lock in Essex escape, but how your package is structured is totally up to you. Pick from any combination of flights, hotels and rental cars. Searching for some tours or activities to keep you on the go? Once you've made your booking, you can add them on too. No matter your style or budget, there's a deal to meet your needs.
What should I know before booking an Essex travel package?
A package can be easier on the wallet than separately booking all you need for your trip. For example, combine your flights, hotels and rental cars and score big savings. No matter your holiday plans, you'll find a package that matches your budget.
Can I choose my airline with an Essex Expedia holiday package?
You sure can. We have more than 550 airline partners across the globe, so pick the carrier that matches your budget needs.
If I'm not able to travel, can I cancel my Essex holiday package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Essex holiday package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more information, browse our Customer Service Portal. We'll help you each step of the way.

Discover the most popular places to visit in Essex

Wrigley Field

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

NZ$68
per adult
92% of travellers recommend
Art Institute of Chicago
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.