Winnetka Holidays
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Top hotels in Winnetka
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
30 Jun - 1 Jul
includes taxes & fees
8/10 Very good! (10,133 reviews)
"The hotel is a bit run down, but my room was very clean. The breakfast was good, although it is not included, and for some reason I thought it was. The receptionist was amazing. She was very kind and allowed me to check in early, which I really appreciated. The location is also excellent. I’m giving ..."
Reviewed on 26 Jun, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$278 per night from 6 Jul to 7 Jul
S$278
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,826 reviews)
"Room clean and bed comfortable"
Reviewed on 27 Jun, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$253 per night from 5 Jul to 6 Jul
S$253
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (4,464 reviews)
"Location was great. Everything at the hotel from checkin to chef out was very smooth."
Reviewed on 26 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 Winnetka attractions
What to do in Winnetka
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.
