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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Jun. 26 - Jun. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
Staff was super friendly and helpful

Reviewed on Apr. 1, 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Jun. 20 - Jun. 25
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (24 reviews)
We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!

Reviewed on Mar. 8, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Enjoyed our stay!! Rooms were clean and breakfast was top tier with many options. They don’t have valet, but they do have self pay parking across the street for $55 a day. Front desk staff professional and helpful.

Reviewed on Apr. 1, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 26 - Jun. 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Nice swimming pool for lap swimming.

Reviewed on Mar. 23, 2025

21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 26 - Jun. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,895 reviews)
The property was a hotel inside a art museum... the artwork was very nice... The handle in shower got stuck on the first day and service came in 5 minutes and no other issues.. Staff was great... check in and out was smooth... I didn't like that parking was 75 dollars a day so we parked at another parking place next door... and fees and extra deposits were unexpected but the experience and weekend was great... I would stay at this hotel again....

Reviewed on Mar. 30, 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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Essex Hotel Deals

Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $132 per night from Apr. 6 to Apr. 7
CA $132
CA $155 total
includes taxes & fees
Apr 6 - Apr 7
8.6/10 Excellent! (1,022 reviews)
"Its really a good hotel and at a good.location and easy to commute"

Reviewed on Mar. 29, 2025

Crowne Plaza Chicago West Loop by IHG
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Apr. 13 to Apr. 14
CA $246
CA $331 total
includes taxes & fees
Apr 13 - Apr 14
8.8/10 Excellent! (2,017 reviews)
"Easy access to Michigan Avenue. Clean and friendly"

Reviewed on Mar. 31, 2025

Swissotel - Chicago
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 CA $193 per night from Apr. 20 to Apr. 21
CA $193
CA $227 total
includes taxes & fees
Apr 20 - Apr 21
8.2/10 Very Good! (3,817 reviews)
"Very convenient!"

Reviewed on Mar. 31, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 3,917 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Essex vacation package cost?
Our Essex packages, which begin from just CA $711, 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 central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

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

Michigan Avenue

4.5/5(19 reviews)

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

Navy Pier

4.5/5(459 reviews)

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

Navy Pier

Things to do

Flyover in Chicago

Flyover in Chicago

CA $55
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $70
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $64
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge 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.