Darien Vacations from $709
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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.
The Talbott, Autograph Collection
Downtown Chicago
$709
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$885
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Incredible hotel — it was clean, the room was spacious, the staff were incredibly friendly, and it was conveniently located in the heart of downtown, within walking distance of everything we needed.
Reviewed on Aug 21, 2026
Level Chicago Fulton Market
Downtown Chicago
$1,101
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Excellent front desk staff. Great place, very clean with a touch of everyday luxury. Highly recommend!
Reviewed on Aug 21, 2026
Level Chicago - River North
Downtown Chicago
$1,272
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
First time staying here and we were not disappointed at all. We were upgraded to a two room suite and the view was spectacular! Beds were super comfortable with soft bedding and the room had everything we needed. The staff were all really friendly and helpful as well. Would definitely stay again.
Reviewed on Aug 21, 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: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Darien Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$115 nightly
$136 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (10,276 reviews)
"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests ..."
Reviewed on Aug 21, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$132 nightly
$156 total
Aug 23 - Aug 24
Total with taxes and fees
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
$222 nightly
$264 total
Aug 30 - Aug 31
Total with taxes and fees
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 $709 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.
