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.
Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
per person
Apr. 17 - Apr. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (CHI)
8.4/10 Very Good! (999 reviews)
Willie checked us in.....what an amazing man and all the other staff at the dront desk!!!! Exceptional service...room and overall experience. Sister trip this go around. Will bring my husband back soon!!! Thank you all for a wonderful experience.

Reviewed on Jan. 20, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr. 17 - Apr. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,340 reviews)
Would definitely be coming back to this hotel

Reviewed on Jan. 20, 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Apr. 17 - Apr. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (14 reviews)
How nice it was and how close it was

Reviewed on Jan. 13, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Mar. 15 - Mar. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (427 reviews)
Fabulous. Always enjoy my stay here. They are always super nice and accommodating. The building is spotless. Love having a washer and dryer in the room.

Reviewed on Jan. 12, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Mar. 15 - Mar. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Beautiful, spacious room

Reviewed on Jan. 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

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 Millennium Park 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

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 CA $116 per night from Feb. 6 to Feb. 7
CA $116
CA $136 total
includes taxes & fees
Feb 6 - Feb 7
7.8/10 Good! (8,410 reviews)
"I would definitely stay here again. The queen roomis so spacious. There is a mini refrigerator, a safe, two bottles of complimentary bottles of water-nice. There is plenty of drawers to put your clothes in- thoughtful. The congress plaza hotel also included a coffee pot with coffee and tea-conveient. ..."

Reviewed on Jan. 22, 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Feb. 4 to Feb. 5
CA $126
CA $148 total
includes taxes & fees
Feb 4 - Feb 5
8.6/10 Excellent! (3,719 reviews)
"I enjoyed my stay no complaints ☺️"

Reviewed on Jan. 20, 2025

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Feb. 20 to Feb. 21
CA $134
CA $157 total
includes taxes & fees
Feb 20 - Feb 21
8.6/10 Excellent! (2,796 reviews)
"Staycation was very nice. Spa is the absolute best! Service and Ambiance was perfect."

Reviewed on Jan. 19, 2025

Eurostars Magnificent Mile
See all 3,962 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 $831, 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 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
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
McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

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
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $49
per adult
Color Factory Chicago 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.