Essex Vacations from ￥244,713

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The Latest Essex Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥286,676, price is now ￥244,713 per person
￥244,713
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amenities, very clean, wonderful buffet service.

Reviewed on Dec 20, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!

Reviewed on Dec 19, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥325,747, price is now ￥269,370 per person
￥269,370
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Excellent location to stay in the heart of the city.

Reviewed on Dec 17, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥293,078, price is now ￥246,075 per person
￥246,075
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was ￥314,266, price is now ￥267,266 per person
￥267,266
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again

Reviewed on Dec 20, 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

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 ￥13,908 per night from Jan 8 to Jan 9
￥13,908
￥16,328 total
Jan 8 - Jan 9, 2026
includes taxes & fees
8.8/10 Excellent! (3,522 reviews)
Clean room, few dust spots, warm and cozy stay

Reviewed on Dec 20, 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,588 per night from Dec 30 to Dec 31
￥12,588
￥19,526 total
Dec 30 - Dec 31
includes taxes & fees
9.2/10 Wonderful! (2,139 reviews)
Clean, comfortable, convenient.

Reviewed on Dec 19, 2025

Silversmith Hotel Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,118 per night from Dec 21 to Dec 22
￥13,118
￥15,399 total
Dec 21 - Dec 22
includes taxes & fees
8.6/10 Excellent! (1,991 reviews)
Great stay

Reviewed on Dec 19, 2025

Club Quarters Hotel Wacker at Michigan, Chicago
See all 4,433 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 ￥244,713, 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

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
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
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

￥6,839
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,310
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,827
per adult
88% 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.