Darien Holidays
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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
Downtown Chicago
Price was S$908, price is now S$611 per person
S$611
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
The staff was incredible, they went out of their way to assist and resolve immediately with any issues we had. Marina, Terina, Gazelle, Nicky and the engineer were all great, incuding the cleaning staff. Breakfast and coffee and fruit were fantastic. Will definitely recommend to family and friends and visit again, if we come into the city.
Reviewed on 28 Jun, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was S$1,152, price is now S$820 per person
S$820
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.
Reviewed on 28 Jun, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was S$1,862, price is now S$1,331 per person
S$1,331
per person
20 Sept - 23 Sept
found 24 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The Trump hotel is always impeccable and this time was no different. We did bring our newborn (first time parents) and they were beyond accommodating; they provided us a crib.
Reviewed on 28 Jun, 2026
Kinzie Hotel
Downtown Chicago
Price was S$995, price is now S$745 per person
S$745
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,134 reviews)
Room is clean and well appointed. Staff are friendly and helpful. Complimentary happy hour and breakfast are bonus. Above all, the location of this boutique hotel is central and convenient for food and walking to the river front.
Reviewed on 28 Jun, 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was S$987, price is now S$749 per person
S$749
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,047 reviews)
It was an ok stay. Room was clean and the hotel was close to the sites/museums we wanted to see.
Reviewed on 26 Jun, 2026
Top hotels in Darien
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$210 per night from 30 Jun to 1 Jul
S$210
per night
30 Jun - 1 Jul
8/10 Very good! (10,157 reviews)
"This hotel hasn’t been updated in decades. The staff do the best they can with a very old hotel that needs a significant investment to be nice."
Reviewed on 28 Jun, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$386 per night from 4 Jul to 5 Jul
S$386
per night
4 Jul - 5 Jul
8.4/10 Very good! (2,324 reviews)
"Room was clean. Bar and breakfast were just ok."
Reviewed on 28 Jun, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is S$188 per night from 2 Jul to 3 Jul
S$188
per night
2 Jul - 3 Jul
8.8/10 Excellent! (2,748 reviews)
"Awesome place to stay and wine and dine"
Reviewed on 28 Jun, 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.
Stay near popular Darien attractions
What to do in Darien
Chicago: Navy Pier Centennial Wheel Ticket
S$31
per adult
88% of travellers recommend
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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. 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.
