Essex Vacations from $269

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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.

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
Save 100% on your flight
Price was $445, price is now $269 per person
$269
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The cleanliness of the rooms was great and the breakfast buffet was second to none! Location, location, location….. was the best! One block away from the Magnificent Mile, restaurants, and can I say Trader Joe’s? We will definitely come back.

Reviewed on Dec 25, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $662, price is now $378 per person
$378
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Clean rooms & courteous staff

Reviewed on Dec 25, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $567, price is now $334 per person
$334
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,211, price is now $732 per person
$732
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!

Reviewed on Dec 21, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $470, price is now $291 per person
$291
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
The room was fantastic, the rest of the hotel (lobby, gym, bar) is spotless. We arranged an engagement photoshoot in the bar via Laura S (events coordinator) and she was unbelievably helpful in ensuring everything was done correctly and in line with hotel procedure. Will be staying again when we revisit Chicago!

Reviewed on Dec 26, 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
$89 nightly
The price is $105 total per night from Jan 5 to Jan 6
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,549 reviews)
Room was warm Recommend softer toilet paper please

Reviewed on Dec 23, 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $179 total per night from Jan 2 to Jan 3
$179 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.4/10 Very Good! (2,170 reviews)
Clean rooms, extremely friendly staff, onsite Starbucks, Lockwood restaurant was amazing, beautiful gathering area in the lounge. Close to all the Christmas must do’s. Decorated so so beautifully for Christmas!

Reviewed on Dec 24, 2025

Palmer House a Hilton Hotel
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
$88 nightly
The price is $103 total per night from Jan 12 to Jan 13
$103 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
8.6/10 Excellent! (2,014 reviews)
Easy check in. Ready to upgrade. I love how central it is and the water stations on each floor. This is our second time to stay here and will do it again!

Reviewed on Dec 23, 2025

Club Quarters Hotel Wacker at Michigan, Chicago
See all 4,428 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
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Beach Vacations
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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

$44
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$80
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
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.