Darien Vacation Packages

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Top Darien Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on Jul. 16, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul. 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Beautiful and upscale property

Reviewed on Jul. 17, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing place overall

Reviewed on Jul. 15, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

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Darien Hotel Deals

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Aug 5 to Aug 6
CA $203
CA $260 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (1,205 reviews)
"Great location, very clean pools & hot tubs, helpful staff."

Reviewed on Jul. 13, 2025

Harbor Shores on Lake Geneva
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard, Fontana, WI
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Aug 11 to Aug 12
CA $157
CA $208 total
Aug 11 - Aug 12
includes taxes & fees
8.4/10 Very Good! (1,389 reviews)
"We liked that the abbey has restaurants inside the the abbey but also a few local restaurants that you can walk to from the property. Having both an adult and kids pool is a great feature of the property . Also, the property was very walkable with the Geneva Lake shore path right off site . Once ..."

Reviewed on Jul. 17, 2025

Abbey Resort and Avani Spa
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $262 per night from Aug 3 to Aug 4
CA $262
CA $345 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (2,894 reviews)
"I liked it rooms were not so big for the money"

Reviewed on Jul. 14, 2025

Timber Ridge Lodge and Waterpark
See all 898 properties in Darien
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Darien vacation package cost?
You'll find cheap prices from CA $779 on Expedia for your Darien escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Darien costs.
What are the cheapest months to go to Darien?
If you're looking to book a cheap Darien vacation package, consider planning a trip in January, February and April. You'll generally find lower rates on hotels and flights during these quieter months --- ideal for a budget-friendly getaway.
How many days is enough for Darien?
With a well-planned itinerary, you can easily visit the main Darien sights in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Darien vacation for longer.
How to find the best Darien package deals?
Finding a cheap Darien package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Darien package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Darien vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Darien?
If you're considering a spur-of-the-moment Darien adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Darien?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Darien.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and activities. Your accommodations will likely be the biggest expense during your trip to Darien.
  3. Decide how long to go for: Now that you're up to speed on Darien, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your accommodations and airfare: After you've settled on your trip dates and duration, book 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.