Winnetka Vacations from ￥221,432
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The Latest Winnetka Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥274,580, price is now ￥221,432 per person
￥221,432
per person
Mar 16 - Mar 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥395,658, price is now ￥312,870 per person
￥312,870
per person
Mar 26 - Mar 30
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥428,324, price is now ￥339,200 per person
￥339,200
per person
Mar 28 - Apr 1
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥310,730, price is now ￥249,464 per person
￥249,464
per person
Mar 16 - Mar 20
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥290,986, price is now ￥236,196 per person
￥236,196
per person
Mar 16 - Mar 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Find the Best Winnetka Vacation Packages
Winnetka Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,997 per night from Jan 25 to Jan 26
￥13,997
￥16,431 total
Jan 25 - Jan 26
includes taxes & fees
8.8/10 Excellent! (3,660 reviews)
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.
Reviewed on Jan 6, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,702 per night from Jan 17 to Jan 18
￥21,702
￥30,074 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,501 reviews)
Everything was amazing abt my stay
Reviewed on Jan 7, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,344 per night from Jan 17 to Jan 18
￥22,344
￥30,143 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,226 reviews)
Room was very clean and staff was great
Reviewed on Jan 6, 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.
Discover the most popular places to visit in Winnetka
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Winnetka
Skydeck - Willis Tower Admission
￥6,889
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,845
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.
