Darien Vacations from $392

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Your Darien Vacation

There's tons to love about Darien, from its rich history to its spectacular views. When you're ready to spend some time in this captivating city, our Darien vacation packages will be perfect for you. If your trip to Darien includes some sightseeing, hit up well-known attractions like Morton Arboretum, Promenade Bolingbrook and Cog Hill Golf & Country Club. Whatever your travel plans or budget, organizing a tailored Darien vacation is easy with Expedia.

The Latest Darien vacation packages

Price found within the past 48 hours. Click for updated prices.
Hollywood Casino Aurora

Hollywood Casino Aurora

2 out of 5
Price was $1,531, price is now $392 per person
$392
per person
Jul 27 - Jul 30
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
No reviews
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,178, price is now $679 per person
$679
per person
Aug 7 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
The gym is on 43 floor.. amazing

Reviewed on May 31, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,220, price is now $719 per person
$719
per person
Aug 7 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,258 reviews)
Excellent location and good selection of breakfast

Reviewed on Jun 2, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,557, price is now $977 per person
$977
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,399, price is now $884 per person
$884
per person
Aug 7 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (395 reviews)
Great location and well maintained property!

Reviewed on May 29, 2026

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Discover the most popular places to visit in Darien

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Darien

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

$22
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Darien

Darien 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
$155 nightly
The price is $184 total per night from Jun 29 to Jun 30
$184 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,159 reviews)
"Hotel was clean, staff friendly. Old hotel that is being improved. Our room was small but otherwise good for our purposes. Good spot that launch our adventure!"

Reviewed on Jun 3, 2026

Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (2,605 reviews)
"Everything was fantastic! From the check in to the Breakfast Buffet to the Dinner restaurant. The Bellmen were great, they brought our luggage to the room & to the car upon checkout. I highly recommend this hotel. 5 Stars"

Reviewed on Jun 2, 2026

Hyatt Regency O'Hare Chicago
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$141 nightly
The price is $168 total per night from Jul 1 to Jul 2
$168 total
Jul 1 - Jul 2
Total with taxes and fees
8/10 Very Good! (3,049 reviews)
"No toilet paper. Stained curtains. But bed was ok."

Reviewed on Jun 2, 2026

Freehand Chicago
See all 3,943 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.

Find the Best Darien Vacation Packages

Darien Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
22,300
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Galloping Ghost and DuPage Childrens Museum

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Frequently asked questions

How much does a Darien vacation package cost?
You can snap up a vacation package to this destination from $392 on Expedia. However, how much your vacation to Darien costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Darien?
If you're looking to book a cheap Darien vacation package, consider visiting in January, June and August. You'll typically find better prices on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Darien?
With a well-organized schedule, you can easily hit the top Darien attractions in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Darien vacation for longer.
How to find the best Darien package deals?
Use Expedia's handy filters to help you find some of the best Darien package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Darien package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Darien vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Darien?
Secure 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 Darien vacation.
Does Expedia offer Book Now, Pay Later Darien vacation packages?
Set off on your dream trip to Darien with our Book Now, Pay Later vacations. There's no need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up bargains while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.