Darien Vacations from $389
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Chicago Lake Shore Hotel
Kenwood
$389
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (1,004 reviews)
My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!
Reviewed on Sep 22, 2026
Level Chicago – Old Town
Downtown Chicago
$656
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 2026
Stay One Chicago
Downtown Chicago
$1,088
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (12 reviews)
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!
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
$179 nightly
$213 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (5,466 reviews)
"I had a fantastic stay! The location was perfect—right next to the Hello Kitty Café and directly across from the Trump Hotel, which made for a beautiful view from my room. Everything was clean, comfortable, and overall a great experience. The only downside was that only one elevator was operating ..."
Reviewed on Sep 22, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$188 nightly
$223 total
Sep 27 - Sep 28
Total with taxes and fees
8/10 Very Good! (10,192 reviews)
"I’ve stayed here for years. Every riot"
Reviewed on Sep 22, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$208 nightly
$248 total
Oct 24 - Oct 25
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 |
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 $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
- Hotels in Westmont
- Motels in Willowbrook
- Hotels in Burr Ridge
- Hotels in Darien
- Hotels in Downers Grove
- Privatevacationhomes in Downers Grove
- La Quinta Inn & Suites Hotels in Darien
- Hotels in Willowbrook
- 5 Star Hotels in Burr Ridge
- Aparthotels in Woodridge
- Apartments in Oak Brook
- Cottages in Western Springs
- Cabins in Hinsdale
- Hotels in Woodridge
- Pet Friendly in Willowbrook
- 4 Star Hotels in Downers Grove
- Budget in Willowbrook
- Marriott Hotels & Resorts Hotels in Darien
- Flights to Burr Ridge
- Flights to Lemont
- Flights from Atlanta (ATL) to Chicago (MDW)
- Flights to Downers Grove
- Flights to Bolingbrook
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Delta Air Lines Atlanta (ATL) to Chicago (MDW) flights
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Flights to Naperville
- Flights to Bridgeview
- Visit Highland Hills
- Visit Palos Hills
- Where to stay in Tinley Park
- Westchester Vacations
- St. Charles Vacations
- Mayslake Peabody Mansion
- Where to stay in Western Suburbs
- Where to stay in Naperville
- Visit Warrenville
- Visit Downers Grove
- Rosemont Vacations
- West Side All Inclusive Vacation Packages
- Chicago Vacations
- Morton Arboretum
- Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Bellwood Vacations
- Bensenville Vacations
- Where to stay in Oakbrook Terrace
- Chicago All Inclusive Vacation Packages
- SeatGeek Stadium
- Chicago All Inclusive Vacation Packages
- Aurora Vacations
- Visit Bedford Park
- Visit Naperville
- Where to stay in Bridgeview
- Chicago All Inclusive Vacation Packages
- Where to stay in Geneva
- Centennial Beach
- Where to stay in Chicago
- Visit Orland Park
- West Side All Inclusive Vacation Packages
- Naperville Vacations
- Visit Oak Park
- Oak Park Vacations
- Where to stay in Carol Stream
- Visit Burr Ridge
- Central Chicago All Inclusive Vacation Packages
- New City Vacations
- Where to stay in Countryside
- Chicago All Inclusive Vacation Packages
- Visit Franklin Park
- Enterprise Rental Cars in Westmont
- Car rentals in Darien
- Luxury Car Rentals in Bolingbrook
- Car rentals in Woodridge
- Car rentals in Willowbrook
- Car rentals in Downers Grove
- Hertz Rental Cars in Burr Ridge
- Car rentals in Burr Ridge
- Minivan Car Rentals in Downers Grove
- Van Car Rentals in Bolingbrook
- Budget Rental Cars in Willowbrook
- Car rentals in Westmont
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
