Essex Holidays

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Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,105, price is now S$1,733 per person
S$1,733
per person
12 Oct - 19 Oct
found 9 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (2,288 reviews)
Chip painting in shower/tub

Reviewed on 22 Aug, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was S$2,898, price is now S$2,234 per person
S$2,234
per person
12 Oct - 19 Oct
found 9 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Proximity to all gates at airport

Reviewed on 23 Aug, 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
Price was S$2,301, price is now S$1,843 per person
S$1,843
per person
12 Oct - 19 Oct
found 9 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Not worth the price.

Reviewed on 21 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,224, price is now S$1,802 per person
S$1,802
per person
12 Oct - 19 Oct
found 9 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,012 reviews)
It was a very nice place. I don’t agree with the parking fees and then the added on three dollar Eco fee when nursing to be parking right beside it that was the cities and didn’t seem like very of secure parking. It wasn’t fenced in or anything just I don’t understand the fee for the parking Other night. It was a stay

Reviewed on 24 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
Price was S$2,181, price is now S$1,844 per person
S$1,844
per person
12 Oct - 19 Oct
found 9 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (2,393 reviews)
Property was very clean lots to do in the surrounding area. Overall experience was good.

Reviewed on 24 Aug, 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 which includes 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

Top hotels in Essex

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 1 Sept to 2 Sept
S$227
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,218 reviews)
"Friendly"

Reviewed on 24 Aug, 2025

The Wade
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 S$283 per night from 14 Sept to 15 Sept
S$283
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,994 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on 23 Aug, 2025

Congress Plaza Hotel
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 S$229 per night from 3 Sept to 4 Sept
S$229
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,742 reviews)
"I loved the suite idea! The breakfast had a large and varied assortment and great dining area! The staff were obliging and convenient to text for additional towels or housekeeping! Although, trash pickup was noisy at 5am every morning facing the south toward the parking garage. Can you ask for a ..."

Reviewed on 21 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,364 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.

Frequently asked questions

How much does an Essex holiday package cost?
Our Essex packages, which begin from just S$1,733, are an easy way to save money. Pick and choose your favourite hotels, flights and rental car to create a personalised 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 holiday 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 holiday 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 fulfil those holiday fantasies.
Where should I stay in Essex?
A holiday 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 holiday?
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 holiday plans, you'll find a package that matches your budget.
Can I choose my airline with an Essex Expedia holiday 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 holiday package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Essex holiday 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

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
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.