Darien Vacations from $295

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The Latest Darien vacation packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $295 per person
$295
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
Room was gorgeous, felt very luxurious for the price! Front desk staff was great at check out!

Reviewed on Feb 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,354, price is now $684 per person
$684
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast and friendly staff

Reviewed on Feb 28, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $669, price is now $404 per person
$404
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .

Reviewed on Feb 17, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $558, price is now $347 per person
$347
per person
Apr 25 - Apr 28
found 2 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
Save 100% on your flight
Price was $654, price is now $415 per person
$415
per person
May 19 - May 25
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
6.4/10 (105 reviews)
Newly remodeled room.

Reviewed on Oct 11, 2025

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Darien Hotel Deals

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
$142 nightly
The price is $157 total per night from Mar 2 to Mar 3
$157 total
Mar 2 - Mar 3
Total with taxes and fees
8.6/10 Excellent! (1,758 reviews)
Clean comfortable. Great piano bar in the evening

Reviewed on Feb 28, 2026

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
$194 nightly
The price is $216 total per night from Mar 9 to Mar 10
$216 total
Mar 9 - Mar 10
Total with taxes and fees
8.6/10 Excellent! (3,155 reviews)
Clean room. Helpful staff. Well run waterpark. Good food.

Reviewed on Feb 28, 2026

Timber Ridge Lodge and Waterpark
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $154 total per night from Mar 2 to Mar 3
$154 total
Mar 2 - Mar 3
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
The staff was great, attentive and helpful. I would say the room needs to be cleaner. We had cobwebs in the bathroom which resulted in killing a few spiders

Reviewed on Feb 22, 2026

Lake Lawn Resort
See all 854 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 $295 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.