Darien Vacations from $493
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The Latest Darien vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
$976
per person
Nov 28 - Dec 4
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.
Reviewed on Sep 26, 2026
Level Chicago – Old Town
Downtown Chicago
$621
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
Amazing stay for a family of four. The kids loved the pool, and the adults loved the hot tub! It felt close to the action, without being too close. Quiet but walkable to Navy Pier, Michigan Avenue, etc. Nearby multiple grocery stores. The building was well maintained and the neighborhood felt safe. The views from the room were unbelievable (the pictures don't do them justice). I would definitely stay here again.
Reviewed on Sep 26, 2026
The Emily Hotel
Downtown Chicago
$503
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Front desk staff was great as was housekeeping staff. Rooms were nothing special. Shower and bathroom floor had moldy grout. Bed was absolutely awful. Felt like sleeping on golfballs. Bar staff was awful. Wanted a quick drink while waiting for an Uber. Told them to charge to room. Bartender went MIA so we asked, what we assumed was a manager to ring us, he said ‘yep’ then went on to make some drinks, ignoring us. For the $$$ you can find much better hotels.
Reviewed on Sep 27, 2026
Darien Hotel Deals
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
$140 nightly
$155 total
Oct 8 - Oct 9
Total with taxes and fees
8.6/10 Excellent! (2,097 reviews)
"Food good at restaurant."
Reviewed on Sep 27, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
$146 nightly
$166 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (1,439 reviews)
"The rooms are nice and mostly remodeled. At least there is no dreadful carpet in the rooms. The beds could use replacing (at least in our room). It's interesting how so many people keep their phones in their face even though they are customer service staff. I am to ask a question, it was answered ..."
Reviewed on Sep 26, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
$169 nightly
$189 total
Oct 20 - Oct 21
Total with taxes and fees
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 $493 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.
