Darien Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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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.
Top Darien Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,139
per person
Sep 25 - Sep 27
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The service and rooms were excellent. Beds were comfortable and views were to die for. The food at Terra16 was a good but the wait times and food service took to long. Our fruit platter took over a half hour for breakfast. The spa was nice, but the lockers were hard to use or some worked and some did not lock. Front desk was exceptional and property was gorgeous. I would definitely stay again and was very happy with the staff who generally were attentive and kind.
Reviewed on Aug 13, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,424
per person
Oct 2 - Oct 6
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Pendry Chicago
Downtown Chicago
CA $1,454
per person
Oct 1 - Oct 4
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,145 reviews)
Everyone at the Pendry was super nice. I would definitely recommend this hotel. My friend got sick and they offered to run across the street to get her medicine. Exceptional service.
Reviewed on Aug 12, 2026
Ready to book your vacation to Darien?
Darien Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $151
CA $180 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,294 reviews)
"I enjoyed my stay at the Congress Plaza. I had a room on the 11th floor with a terrific view of the lake. One problem: I stayed for two days and no housekeepers ever showed up to clean the room."
Reviewed on Aug 13, 2026
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
CA $224
CA $311 total
Sep 10 - Sep 11
includes taxes & fees
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $235
CA $321 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (3,024 reviews)
"Nice hotel, great location. $72 for parking a night and you have to pay to use the gym at the hotel turned me off."
Reviewed on Aug 12, 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.
Stay near popular Darien attractions
National Shrine of St. Therese
7.4/10 (6 reviews)
You can spend an afternoon exploring the galleries in National Shrine of St. Therese in Darien. Wander the forest and lakeside in this trendy area.
What to do in Darien
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Darien vacation package cost?
Offering great value package deals from CA $1,139 on Expedia, you'll be surprised at how little a vacation to Darien costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Darien?
You can usually find reduced prices and better availability in April, July and November. Browse our cheap Darien vacation packages and you could get some excellent off-season deals.
How many days is enough for Darien?
We'd suggest booking a Darien vacation for at least 3 days. This will allow you time to tick off popular sights such as Seven Bridges Golf Club and Mayslake Peabody Mansion, as well as check out neighbourhoods like Clarendon Hills and Indian Head Park. You could even squeeze in one or two day trips from Darien.
How to find the best Darien package deals?
Use Expedia's filter tool to help you find some of the best Darien package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Darien package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still get the freedom to create a customized Darien vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Darien?
If you've got your Darien travel dates confirmed, book as early as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Darien?
- Choose your travel dates: The things you'd like to do in Darien and your favourite season can help you decide when to go.
- Set your budget: Consider expenses like food, flights and transportation when working out how much to save for your trip to Darien. Then, pick a hotel that matches your budget, whether that's a low-cost option or a lavish getaway.
- Decide how long to go away for: Now that you're up to speed on Darien, you can figure out the ideal length of your break. Pull together a rough plan and allocate enough time for all the things you want to do.
- Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the ideal Darien vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
