Darien Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Darien Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 22 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Staff were so helpful and friendly

Reviewed on 16 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 22 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The location is great, with a fantastic staff and an easy check-in process. I can walk to almost everything, and the bus station is right next to the door.

Reviewed on 16 Jul, 2025

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
per person
27 Sept - 29 Sept
found 22 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Great location, but the $50.00 early check-in fee is ridiculous. Also, the comforter on the bed has seen better days.

Reviewed on 15 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 22 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 22 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Clean and the suites are room

Reviewed on 16 Jul, 2025

Top hotels in Darien

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
The price is S$271 per night from 3 Aug to 4 Aug
S$271
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (1,204 reviews)
"Great location, very clean pools & hot tubs, helpful staff."

Reviewed on 13 Jul, 2025

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
The price is S$212 per night from 6 Aug to 7 Aug
S$212
6 Aug - 7 Aug
includes taxes & fees
8.4/10 Very Good! (1,396 reviews)
"Nice hotel in a beautiful location!"

Reviewed on 12 Jul, 2025

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
The price is S$324 per night from 3 Aug to 4 Aug
S$324
3 Aug - 4 Aug
includes taxes & fees
8.6/10 Excellent! (2,892 reviews)
"My family stayed there for a few nights and it was nice."

Reviewed on 13 Jul, 2025

Timber Ridge Lodge and Waterpark
See all 898 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.

Frequently asked questions

How much does a Darien holiday package cost?
You can pick up a holiday package to this top destination from S$437 on Expedia. However, how much your holiday 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're hoping to snag a cheap Darien holiday package, consider visiting in January, February and April. You'll generally find lower rates on flights and accommodation during these months --- ideal for travellers wishing to save money.
How many days is enough for Darien?
With a well-organised travel plan, you can easily hit the main Darien attractions in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Darien holiday for longer.
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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Darien holiday as a package?
You can enjoy significant savings on your next Darien getaway by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday 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.
How to plan a trip to Darien?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Darien.
  2. Budget wisely: Besides the price of your hotel, you should factor in other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that may arise during your trip to Darien.
  3. Decide how long to go away for: Now that you're more familiar with Darien, you can work out the right length of your holiday. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Darien holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.