Darien Holidays
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Top Flight + Hotel Deals in Darien
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,602, price is now €1,341 per person
€1,341
per person
10 Jul - 13 Jul
found 14 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Lovely stay and we are at Toro right in the hotel. Fabulous dinner
Reviewed on 18 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €2,084, price is now €1,682 per person
€1,682
per person
10 Jul - 13 Jul
found 14 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Great experience! Would stay here agin
Reviewed on 18 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,886, price is now €1,522 per person
€1,522
per person
10 Jul - 13 Jul
found 14 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
I loved it here and will definitely stay again.
Reviewed on 18 May 2026
Pendry Chicago
Downtown Chicago
Price was €1,862, price is now €1,549 per person
€1,549
per person
10 Jul - 13 Jul
found 14 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on 27 Apr 2026
Top hotels in Darien
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is €115 per night from 21 May to 22 May
€115
21 May - 22 May
includes taxes & fees
9.2/10 Wonderful! (1,343 reviews)
"Major construction outside hotel. It affects the view from balconies and traffic around building."
Reviewed on 19 May 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is €167 per night from 7 Jun to 8 Jun
€167
7 Jun - 8 Jun
includes taxes & fees
8.6/10 Excellent! (1,883 reviews)
"This was our third stay at the Abbey and while we always have a wonderful time, this time was a little underwhelming on site. The first night of our stay they were reroofing a building which was very noisy - we woke up to this again at 7:30a Saturday morning and it continued throughout the morning. ..."
Reviewed on 19 May 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is €186 per night from 25 May to 26 May
€186
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (3,256 reviews)
"Good family fun"
Reviewed on 17 May 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
