Essex Vacations from $245

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The Latest Essex vacation packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Chicago - Alsip

Red Roof Inn Chicago - Alsip

2.5 out of 5
Price was $313, price is now $245 per person
$245
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
6/10 (597 reviews)
Very nices motel greaful for this places real consider this location to all a very caring place to be

Reviewed on Oct 17, 2025

Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Price was $347, price is now $266 per person
$266
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
8.2/10 Very Good! (1,018 reviews)
Front desk and housekeeping staff were very polite. The hotel can use a few upgrades.

Reviewed on Oct 26, 2025

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Price was $727, price is now $564 per person
$564
per person
Nov 26 - Nov 30
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
9.4/10 Exceptional! (138 reviews)
I had a 2 night stay and was pleasantly surprised. My room was spacious and beautifully furnished and decorated. I spent 4 hours in the spa and was very impressed with the level of service and amenities. On our last night we had dinner at Alto,s. Omg !!! So good ! This was my 2nd visit and it was as good as the first. I had crab cakes as appetizers and lamb chops as my entree. This was the best lamb chops I have had . I would revisit Wind creek to dine at Alto,s. This was a weekend getaway and it was superb!!!!

Reviewed on Oct 25, 2025

Quality Inn Monee I-57

Quality Inn Monee I-57

2.5 out of 5
Price was $488, price is now $424 per person
$424
per person
Dec 28 - Dec 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Chicago (MDW)
6.6/10 (530 reviews)
Much begter than a year ago!! Nice job. Pool is open again.

Reviewed on Aug 24, 2025

Kings Inn By OYO Calumet Park I-57

Kings Inn By OYO Calumet Park I-57

2.5 out of 5
Price was $476, price is now $415 per person
$415
per person
Dec 28 - Dec 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Chicago (MDW)
4.8/10 (605 reviews)
Ouiet stay Polite staff

Reviewed on Jan 7, 2025

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Essex Hotel Deals

Comfort Inn Bourbonnais near I-57

Comfort Inn Bourbonnais near I-57

2.5 out of 5
1500 Illinois Highway 50, Bourbonnais, IL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Nov 23 to Nov 24
$80 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,011 reviews)
It was ok.

Reviewed on Oct 11, 2025

Comfort Inn Bourbonnais near I-57
Holiday Inn Express & Suites Bourbonnais East - Bradley by IHG

Holiday Inn Express & Suites Bourbonnais East - Bradley by IHG

2.5 out of 5
1000 FREEDOM DRIVE, Bourbonnais, IL
Fully refundable
$95 nightly
The price is $105 total per night from Nov 16 to Nov 17
$105 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (443 reviews)
Bacon at breakfast wi up la be nice

Reviewed on Oct 24, 2025

Holiday Inn Express & Suites Bourbonnais East - Bradley by IHG
Best Western Plus Bourbonnais Hotel & Suites

Best Western Plus Bourbonnais Hotel & Suites

2.5 out of 5
62 Ken Hayes Dr, Bourbonnais, IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $98 total per night from Nov 2 to Nov 3
$98 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (496 reviews)
Everyone was friendly and the breakfast was delicious

Reviewed on Oct 20, 2025

Best Western Plus Bourbonnais Hotel & Suites
See all 74 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.

Find the Best Essex Vacation Packages

Essex Essential Information

Language
English
Currency
U.S dollars
Population
770

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Frequently asked questions

How much does an Essex vacation package cost?
Offering excellent value package deals from $245 on Expedia, you'll be pleasantly surprised at how much a vacation to Essex costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Essex?
You're likely to find reduced prices and better availability in January, March and December. Take a look at our cheap Essex vacation packages and you could land some excellent off-season deals.
How many days is enough for Essex?
With a well-organized travel plan, you can easily hit the main Essex attractions in a handful of days. But if you'd like to discover hidden gems or take day trips, consider booking your Essex vacation for longer.
How to find the best Essex package deals?
Bagging a cheap Essex package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Essex package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Essex vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels separately. Better still, you can personalize your Essex escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Essex?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Essex trip.
Does Expedia offer Book Now, Pay Later Essex vacation packages?
Secure your dream getaway to Essex with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.