Winnetka Packages (Flight + Hotel)
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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 ฿4,553 per night from 30 Jun to 1 Jul
฿4,553
฿5,413 total
30 Jun - 1 Jul
includes taxes & fees
8/10 Very good! (10,134 reviews)
"The Congress was my number #1 place for 30 years. It's an older hotel and shows. Doors in my suite don't close or lock correctly. The room wasn't cleaned when requested so my travel mate could make bets if the room was serviced or not by the time we returned. Not even when I called House keeping. ..."
Reviewed on 27 Jun 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿5,100 per night from 5 Jul to 6 Jul
฿5,100
฿7,175 total
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,827 reviews)
"The staff were very helpful and kind, room clean and a beautiful view. Hotel kept up very well. Our air conditioning worked great on the 23rd floor. Check out, bags held and valet parking plus retrieval very quick and excellent service."
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 ฿5,500 per night from 5 Jul to 6 Jul
฿5,500
฿6,539 total
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (4,465 reviews)
"Excellent room for a small family. Staff was friendly, room was clean. Perfect location."
Reviewed on 27 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 CityPASS®: Experience 5 must-see attractions
฿4,731
per adult
94% 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.
