Darien Vacations from $586
Book a Hotel + Flight or Car together to unlock savings
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.
Four Seasons Hotel Chicago
Downtown Chicago
$1,169
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$969
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 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
Darien Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$101 nightly
$120 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (10,257 reviews)
"Was a fun time had by all"
Reviewed on Sep 2, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$161 nightly
$192 total
Sep 8 - Sep 9
Total with taxes and fees
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$197 nightly
$231 total
Sep 10 - Sep 11
Total with taxes and fees
8.6/10 Excellent! (3,131 reviews)
"Overall it was a very good experience. The only thing I would comment is that the conditioner is empty when we arrived I called the lobby and left a message that I need conditioner the auto-robot operator said it will be sent to.our room but it never arrived."
Reviewed on Sep 2, 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 |
More vacations you might like
Frequently asked questions
How much does a Darien vacation package cost?
You can snap up a vacation package to this destination from $586 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
- Robert W Roloson Houses
- Rookery
- Humboldt Park
- Fourth Presbyterian Church
- Promenade Bolingbrook
- 900 North Michigan Shops
- Richard J. Daley Center
- Chicago Museum Campus Vacations
- Downers Grove Vacations
- Palisades Vacations
- Auditorium Building and Theatre
- Magnificent Mile Vacations
- Burr Ridge Vacations
- Rocket Ice Arena
- Canalport Riverwalk Park
- Willowbrook Vacations
- Film Row Cinema
- Chicago City Hall
- Chicago Vacations
- Willis Tower
- Chicago Place Mall
- Wheaton College
- Lincoln Park Zoo
- Michigan Avenue
- Jane Addams' Hull-House Museum
- Fisher Building
- Raging Waves Waterpark
- Anna and Frederick Douglass Park
- Marina City
- Unity Temple
- Tribune Tower
- Veterans Memorial Park
- Chase Tower
- Wicker Park Vacations
- Graue Mill and Museum
- Merchandise Mart
- Skydeck Ledge
- Willowbrook Community Park
- Chinatown Vacations
- West Loop Vacations
- American Police Center & Museum
- Monique Meloche Gallery
- Westmont Vacations
- St. Basil Greek Orthodox Church
- Ty Warner Park
- Grace Abbott Homes Vacations
- 333 West Wacker Drive
- Roosevelt University
- Wrigley Building
- Monadnock Building
- Marshall Field Building
- Our Lady of Sorrows Basilica
- Depaul University-Loop Campus
- Gen. John Logan Memorial
- Maxwell Street Market
- Civic Opera House
- Centennial Beach
- Shops at North Bridge
- St. John Cantius Church
- Illinois Centennial Memorial Column
- South Loop Vacations
- Cadillac Palace Theatre
- Bridgeport Art Center
- Ping Tom Memorial Park
- Flat Iron Building
- Holy Name Cathedral
- Mary Bartelme Park
- Sr Crown Hall
- Gorilla Tango Theatre
- South Commons Vacations
- The East Bank Club
- 311 S Wacker Dr
- Goodman Theater
- Morton Arboretum
- Robie House
- Zhou B Art Center
- Mayslake Peabody Mansion
- Chicago Children's Museum
- Picasso Statue
- Ida B Wells House
- Montrose Beach
- Wrigley Field
- Seatgeek Stadium
- Navy Pier
- Burnham Park
- Carbide and Carbon Building
- Cantigny Park
- Cibc Theatre
- Art Institute of Chicago
- The Salt Shed
- Packer Schopf Gallery
- Legoland® Discovery Center
- University of Illinois Chicago
- Creekside Park
- St Nicholas Ukrainian Catholic Cathedral
- Cooking & Hospitality Institute of Chicago
- Garfield Park
- Mccormick Tribune Center
- Driehaus Museum
- Holy Trinity Russian Orthodox Cathedral
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.