Darien Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Darien Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 1 day ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
7.8/10 Good! (7,993 reviews)
Definitely was a night to remember staying here! Very beautiful style!

Reviewed on 22 Nov,2024

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 1 day ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
8.2/10 Very Good! (2,454 reviews)
Easy transfer to other transportation.

Reviewed on 22 Nov,2024

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 1 day ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
8.8/10 Excellent! (1,730 reviews)
Staff was excellent, room is comfortable

Reviewed on 17 Nov,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Darien

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$135 per night from 25 Nov to 26 Nov
S$135
includes taxes & fees
25 Nov - 26 Nov
7.8/10 Good! (8,142 reviews)
"Ice machines! This was an issue here all summer long. I pointed it out to management over the summer but the issue has gone from bad to worse. Supposedly, there are ice machines on even floors. This visit, housekeeping directed me to the machine on the 4th floor as the only working ice machine. I ..."

Reviewed on 22 Nov,2024

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 S$157 per night from 23 Dec to 24 Dec
S$157
includes taxes & fees
23 Dec - 24 Dec
8.6/10 Excellent! (3,542 reviews)
"Highly recommend ."

Reviewed on 20 Nov,2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$151 per night from 23 Dec to 24 Dec
S$151
includes taxes & fees
23 Dec - 24 Dec
8.4/10 Very Good! (3,264 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

Reviewed on 21 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 3,373 properties in Darien
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 a Darien holiday package cost?
We make it easy to explore the world, with Darien packages starting from as little as S$1,648. You’ll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate escape, why not add a few tours and activities to your travel itinerary?
How do I get a cheap travel package to Darien?
If you love bargains, bundle your bookings into a Darien holiday package. Whether you’re searching for flights, hotels, rental cars or tours, you can browse and book everything in one place. You’ll have ample choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 hotel options globally to select from. Fly with who you prefer, stay where you like and save your hard-earned money — now that’s the perfect holiday!
Where should I stay in Darien?
With so much to discover in Darien, it’d be convenient for you to book a room in a hotel near its attractions. National Shrine of St. Therese, Twin Lakes Park and Willowbrook Community Park are some interesting ones to add to your itinerary.
What are the top hotels in Darien?
WoodSpring Suites Chicago Darien and Extended Stay America Suites Chicago Darien are two of the most well-known hotels in Darien. Why not take a look at the rates and amenities at each and then make a decision?
How far in advance should I book my Darien holiday?
Get rewarded with the biggest variety at the lowest prices by booking your trip to Darien early. Air carriers usually sell tickets anywhere up to 12 months prior to departure, so start your planning as soon as possible. That being said, Expedia is constantly working to give you the best bargains around, so it’s never a bad time to book your dream holiday!
What does an Expedia Darien travel package include?
With Expedia, you can select any combination of car rentals, flights and hotels to create your perfect Darien travel package. Once you’ve made your booking, you can add on fun stuff like sightseeing tours and activities. Remember, the more you bundle, the more cash you’ll save!
What should I know before booking a Darien travel package?
Design deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You’ll save big bucks just for bundling your bookings. Whether you’re taking off on a winter adventure or relaxing on a sunny beach, your perfect holiday is just a few clicks away.
Can I choose my airline with a Darien Expedia holiday package?
Yes — that’s the beauty of an Expedia holiday package. You’re in control. We have access to more than 550 partner airlines worldwide, so you have options galore when putting together your Darien trip.
If I'm not able to travel, can I cancel my Darien holiday package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can cancel or change your Darien holiday package. If you booked in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 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
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

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

Millennium Park

4.5/5(147 reviews)

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

Millennium Park

What to do in Darien

Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$71
Per adult
94% of travellers recommend
Architecture River Tour
Narrated by certified, local docent

Chicago Architecture Center River Cruise aboard Chicago's First Lady

S$71
Per adult
98% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Darien

* 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.