Darien Vacations from $320

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The Latest Darien vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (1,005 reviews)
This hotel was clean, amazing breakfast, service and staff were friendly as can be and helpful! Stayed for three days and loved it!

Reviewed on Jun 1, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 5
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (CHI)
8.4/10 Very Good! (998 reviews)
Very disappointed with the lack of dining options and the fact that there’s no complimentary coffee or water available in the lobby. We will not stay here again

Reviewed on Jun 10, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,079 reviews)
It near the airport.

Reviewed on Jun 26, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (211 reviews)
other than the mold on the soap dispenser this hotel is beautiful

Reviewed on Jun 27, 2025

Holiday Inn Chicago North Shore by IHG

Holiday Inn Chicago North Shore by IHG

3 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.4/10 Good! (1,221 reviews)
The staff was extremely helpful and knowledgeable. It was a very clean and quiet place to stay. The veiw was lovely as well. The building was very easy to navigate and get from our room to the outside with no issues. Will definitely use this hotel next time im in the area!

Reviewed on Jun 28, 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
$129 nightly
The price is $142 total per night from Jul 1 to Jul 2
$142 total
Jul 1 - Jul 2
Total includes taxes and fees
8.4/10 Very Good! (1,352 reviews)
"A wonderful place for a girls weekend! My two adult daughters, granddaughter and I enjoyed our trip here very much! The property is beautiful with stunning views and very peaceful! The staff was all kind, polite and tried to accommodate any requests we had. Our room was decorated perfect for a lake ..."

Reviewed on Jun 26, 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
$174 nightly
The price is $197 total per night from Jun 29 to Jun 30
$197 total
Jun 29 - Jun 30
Total includes taxes and fees
9/10 Wonderful! (1,194 reviews)
"Great staff!"

Reviewed on Jun 25, 2025

Harbor Shores on Lake Geneva
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
$251 nightly
The price is $280 total per night from Jul 29 to Jul 30
$280 total
Jul 29 - Jul 30
Total includes taxes and fees
8.6/10 Excellent! (2,866 reviews)
"Very good."

Reviewed on Jun 25, 2025

Timber Ridge Lodge and Waterpark
See all 881 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 $320 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.