Darien Vacations from $389
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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.
Trump International Hotel & Tower Chicago
Downtown Chicago
$981
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.
Reviewed on Sep 20, 2026
Stay near popular Darien attractions
National Shrine of St. Therese
7.4/10 (6 reviews)
This tranquil shrine houses the largest collection of St. Therese's personal effects outside France. Explore the museum's first-class relics and replica convent cell before reflecting in the serene garden sanctuary.
What to do in Darien
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Darien Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$189 nightly
$224 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (5,452 reviews)
"great location, decent amount of space at a reasonable price (for nowadays)"
Reviewed on Sep 20, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$205 nightly
$244 total
Sep 27 - Sep 28
Total with taxes and fees
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$236 nightly
$281 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (3,271 reviews)
"We loved the historic aspects of the hotel. It takes up an entire city block and is packed with so much history celebrating nearly 100 years in business. However that comes with the downside of lower ceilings, older rooms, etc. the room was small but very clean and reasonable, I just prefer something ..."
Reviewed on Sep 21, 2026
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 $389 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
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
