Essex Vacations from ￥242,202

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Essex Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥253,520, price is now ￥242,202 per person
￥242,202
per person
Jan 17 - Jan 21
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,037 reviews)
This hotel was absolutely amazing . It was clean spacious and very upscale for this price point ! Accessible to a lot of shops a restaurants . Will definitely stay again & again!

Reviewed on Oct 26, 2025

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥269,080, price is now ￥248,740 per person
￥248,740
per person
Jan 17 - Jan 21
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,583 reviews)
Staff was really welcoming! Valet staff were very helpful! The suite was okay: bed was really comfortable but bathroom is slightly dated with no ventilation…

Reviewed on Oct 30, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was ￥260,844, price is now ￥244,204 per person
￥244,204
per person
Jan 17 - Jan 21
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,382 reviews)
The hotel was located in a safe, convenient location. The room maximizes space for an efficient stay plus all the amenities you would expect, plus some. The in-hotel restaurant ioffers an outstanding menu, great service. Room was squeaky clean. Nice, safe, quiet, and convenient stay. Downsides: the valet was inattentive (not to be found) when we pulled up a little after 8 PM as was the bellman whose duties end at 7:30. The good news, parking is literally around the corner and the bellman carts around the corner from the front desk. So, a little self-service never hurt anyone.

Reviewed on Oct 31, 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 showing 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

Essex Hotel Deals

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 ￥18,194 per night from Nov 23 to Nov 24
￥18,194
￥21,358 total
Nov 23 - Nov 24
includes taxes & fees
8.4/10 Very Good! (5,174 reviews)
Completely fell in love with the hotel!

Reviewed on Oct 30, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ￥14,460 per night from Nov 24 to Nov 25
￥14,460
￥16,975 total
Nov 24 - Nov 25
includes taxes & fees
7.8/10 Good! (9,638 reviews)
Clean but older room.

Reviewed on Oct 31, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥10,362 per night from Nov 26 to Nov 27
￥10,362
￥14,876 total
Nov 26 - Nov 27
includes taxes & fees
7.8/10 Good! (2,551 reviews)
Room was clean and stocked with bodywash, shampoo, handsoap. Staff were courteous.

Reviewed on Oct 31, 2025

Freehand Chicago
See all 4,315 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 vacation package cost?
Our Essex packages, which begin from just ￥242,202, are an easy way to save money. Pick and choose your favorite hotels, flights and rental car to create a personalized 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 vacation 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 vacation 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 fulfill those vacation fantasies.
Where should I stay in Essex?
A vacation 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 vacation?
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 vacation plans, you'll find a package that matches your budget.
Can I choose my airline with an Essex Expedia vacation 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 vacation package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Essex vacation 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 featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy 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
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,404
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

￥6,612
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,691
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.