Central Chicago Romantic Vacations
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Top Romantic vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥198,952, price is now ￥152,105 per person
￥152,105
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on Dec 8, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥355,415, price is now ￥261,880 per person
￥261,880
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing
Reviewed on Dec 16, 2025
The Emily Hotel
Downtown Chicago
Price was ￥230,337, price is now ￥177,390 per person
￥177,390
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Love staying at the Emily. Very helpful friendly Staff & ccool architecture. Also love the front Patio in Summer☀️
Reviewed on Dec 16, 2025
Pendry Chicago
Downtown Chicago
Price was ￥208,927, price is now ￥161,814 per person
￥161,814
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Excellent location to stay in the heart of the city.
Reviewed on Dec 17, 2025
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See all available trips from Tokyo to Central Chicago
View all trips5* Romantic vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥355,415, price is now ￥261,880 per person
￥261,880
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing
Reviewed on Dec 16, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥393,998, price is now ￥304,081 per person
￥304,081
per person
Mar 2 - Mar 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Parking garage attatched to hotel is large and easy to use. I booked early with spot hero, and had no problems. The staff is inviting and helpful. I booked the king lake view, it had a beautiful view of the river, city, and lake. The room itself was clean, quiet, and well furnished. This hotel was the highlight of our trip.
Reviewed on Dec 18, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥420,340, price is now ￥330,843 per person
￥330,843
per person
Mar 2 - Mar 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
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See all available trips from Tokyo to Central Chicago
View all trips3 Night Romantic vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was ￥268,114, price is now ￥248,706 per person
￥248,706
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,062 reviews)
Excellent staff. Clean room with comfortable bed and pillows. Only issue was there was no hot water the next morning. Granted it was 5 degrees outside but still a little disappointing
Reviewed on Dec 17, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥288,441, price is now ￥259,148 per person
￥259,148
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was ￥273,664, price is now ￥253,878 per person
￥253,878
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
It’s amazing historical property
Reviewed on Dec 15, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips4 Night Romantic vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥292,616, price is now ￥245,230 per person
￥245,230
per person
Mar 2 - Mar 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was nice. Service was good.
Reviewed on Dec 17, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥393,998, price is now ￥304,081 per person
￥304,081
per person
Mar 2 - Mar 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Parking garage attatched to hotel is large and easy to use. I booked early with spot hero, and had no problems. The staff is inviting and helpful. I booked the king lake view, it had a beautiful view of the river, city, and lake. The room itself was clean, quiet, and well furnished. This hotel was the highlight of our trip.
Reviewed on Dec 18, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥420,340, price is now ￥330,843 per person
￥330,843
per person
Mar 2 - Mar 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
