Darien Holidays

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Top Flight + Hotel Deals in Darien

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
just found
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on 21 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
just found
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Самый лучший отель в чикаго

Reviewed on 28 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
just found
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
Will definitely stay here again

Reviewed on 28 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
just found
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
just found
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 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
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,206 reviews)
"Easy check in and out."

Reviewed on 25 Jul 2025

Get rates
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
The price is €125 per night from 24 Aug to 25 Aug
€125
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (1,414 reviews)
"While the lobby and dining rooms have been remodeled, some areas, like the outside pool and outside balconies are in high need of repair. The grounds are beautiful. The rooms were musty smelling and no privacy. Our rooms looked out on to the grounds, but if we opened the blinds, everyone could see ..."

Reviewed on 23 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 €200 per night from 31 Jul to 1 Aug
€200
31 Jul - 1 Aug
includes taxes & fees
8.6/10 Excellent! (2,902 reviews)
"We chose Timber Ridge for its proximity to Alpine Valley Music Theater and it was mission accomplished. This is a great place for families with young kids. Everyone was having a blast."

Reviewed on 22 Jul 2025

Timber Ridge Lodge and Waterpark
See all 904 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 €720 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.