Darien Vacations from $144

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The Latest Darien vacation packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $313, price is now $144 per person
$144
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Everything was perfect

Reviewed on Nov 12, 2025

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $668, price is now $334 per person
$334
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Best location to stay

Reviewed on Oct 25, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $384, price is now $196 per person
$196
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.

Reviewed on Nov 12, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Price was $526, price is now $275 per person
$275
per person
Dec 31 - Jan 3
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (154 reviews)
Beautiful place, friendly staff. We loved the restaurant.

Reviewed on Nov 1, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $493, price is now $261 per person
$261
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

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Darien Hotel Deals

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
$194 nightly
The price is $216 total per night from Nov 19 to Nov 20
$216 total
Nov 19 - Nov 20
Total with taxes and fees
8.6/10 Excellent! (3,031 reviews)
Receptionists was so kind and professional life guards v3ry attended

Reviewed on Nov 12, 2025

Timber Ridge Lodge and Waterpark
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
$152 nightly
The price is $168 total per night from Nov 16 to Nov 17
$168 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (1,642 reviews)
Great hotel

Reviewed on Nov 12, 2025

Abbey Resort and Avani Spa
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
$121 nightly
The price is $137 total per night from Nov 16 to Nov 17
$137 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (1,316 reviews)
Yes

Reviewed on Nov 10, 2025

Harbor Shores on Lake Geneva
See all 845 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.

Find the Best Darien Vacation Packages

Darien Essential Information

Language
English
Currency
U.S dollars
Population
1,600
Top Sights
Dancing Horse Theatre, Staller Estate Winery and Animal Gardens

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Frequently asked questions

How much does a Darien vacation package cost?
You can pick up a vacation package to this top destination from $144 on Expedia. However, how much your vacation to Darien costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Darien?
If you'd like to score a cheap Darien vacation package, consider visiting in October, November and December. You'll usually find better prices on airfares and hotels during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Darien?
Usually, a handful of days is enough to visit the main sights during your Darien vacation. However, if you prefer to have more time to kick back or go on day trips, consider extending your itinerary.
How to find the best Darien package deals?
Landing a cheap Darien package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most economical Darien package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Darien vacation as a package?
You can enjoy significant savings on your next Darien getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Darien?
If you're considering a spur-of-the-moment Darien adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Darien vacation packages?
Your Darien getaway should be an escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.