Essex Vacation Packages

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Your Essex Vacation

When a break in the city is calling, answer it with a vacation package to Essex. The neighborhood 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, organizing a tailored Essex vacation is a walk in the park with Expedia.

Top Holiday Package Deals in Essex

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $894
per person
Oct 23 - Oct 26
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Beautiful hotel and fantastic staff.

Reviewed on Sep 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,022
per person
Oct 23 - Oct 26
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The hotel was so amazing for us. Staff was accommodating and helped us immensely. The restaurant for breakfast and the roof top wil keep you coming back. We will try to stay there as much as we can while in Chicago.. Lester and Luis at the restaurants need a bonus. They kept the breakfast crowd well organized.

Reviewed on Sep 4, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,312
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Freehand Chicago

Freehand Chicago

Downtown Chicago
CA $1,759
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
7.8/10 Good! (3,367 reviews)
Excelente atención sobre todo de Dana y Alex siempre atentas a lo que necesitábamos … los ascensores funcionaban a la perfección… todo fue muy muy buena experiencia. Solo cambiaría el color de los pasillos y del ascensor. Pero solo como consejo después de eso más que bien !!!

Reviewed on Sep 4, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,153
per person
Oct 21 - Oct 24
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Cute hotel in great location..make sure to ask for a street side room or your view will be a brick wall and the room will be like a dark cave. 😭

Reviewed on Sep 4, 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

4 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
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

Find hotels in The Loop
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Essex Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
CA $159
CA $189 total
Sep 7 - Sep 8
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $183
CA $218 total
Sep 30 - Oct 1
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"

Reviewed on Sep 4, 2026

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Kasa Magnificent Mile Chicago
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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.
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Frequently asked questions

How much does an Essex vacation package cost?
Our Essex packages, which begin from just CA $894, 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.