Darien Vacations from $702

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The Latest Darien vacation packages

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,345, price is now $702 per person
$702
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!

Reviewed on May 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,475, price is now $769 per person
$769
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Wonderful experience, beautiful place. Breakfast on site was a huge plus!

Reviewed on May 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,622, price is now $1,002 per person
$1,002
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,454, price is now $915 per person
$915
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location. Very friendly and helpful staff.

Reviewed on May 13, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,404, price is now $908 per person
$908
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

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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
$121 nightly
The price is $137 total per night from May 17 to May 18
$137 total
May 17 - May 18
Total with taxes and fees
9.2/10 Wonderful! (1,349 reviews)
Rooms are very well thought out lots of storage, but uncluttered and ultra clean. I loved that there were no cleaning product or other fumes in the room. The place had no artificial odors whatsoever. No glade plug-ins or other obnoxious air freshener smells, I really appreciate that!!! The check-in ...

Reviewed on May 14, 2026

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
$174 nightly
The price is $193 total per night from May 19 to May 20
$193 total
May 19 - May 20
Total with taxes and fees
8.6/10 Excellent! (1,876 reviews)
Room was clean and hotel was well kept. Spa was okay not great

Reviewed on May 12, 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
$171 nightly
The price is $191 total per night from May 20 to May 21
$191 total
May 20 - May 21
Total with taxes and fees
8.6/10 Excellent! (3,255 reviews)
Kathy in the gift shop was fantastic. And Yolanda at the front desk.

Reviewed on May 12, 2026

Timber Ridge Lodge and Waterpark
See all 877 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 $702 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.