Illinois Romantic Vacations
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Top Romantic vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥456,542, price is now ￥371,712 per person
￥371,712
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥338,290, price is now ￥283,958 per person
￥283,958
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience
Reviewed on Oct 31, 2025
Swissotel - Chicago
Downtown Chicago
Price was ￥465,548, price is now ￥393,530 per person
￥393,530
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
Front desk and room service staff were great. Clean room great views
Reviewed on Oct 30, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥473,515, price is now ￥400,650 per person
￥400,650
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
Everything about this Hotel was top tier and prestigious. Highly recommended. Rooms were extremely clean, Staff super friendly and the Breakfast was delicious. You have to try the pancakes and French toast
Reviewed on Oct 27, 2025
5* Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥338,290, price is now ￥283,958 per person
￥283,958
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience
Reviewed on Oct 31, 2025
3 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥196,670, price is now ￥177,360 per person
￥177,360
per person
Dec 25 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
Naha (OKA) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Price was ￥199,259, price is now ￥183,468 per person
￥183,468
per person
Dec 25 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
Naha (OKA) to Chicago (ORD)
8.4/10 Very Good! (1,736 reviews)
The room was spotless...I was there for the tub which did not disappoint... It was clean deep and relaxing.
Reviewed on Oct 30, 2025
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥205,774, price is now ￥191,340 per person
￥191,340
per person
Dec 25 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
Naha (OKA) to Chicago (ORD)
9/10 Wonderful! (3,081 reviews)
The location was so spectacular. The staff was courteous and knowledgeable. I stayed in the panoramic room and it gave me exactly what I was expecting which was nice views. I would definitely stay here again.
Reviewed on Oct 30, 2025
4 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥338,290, price is now ￥283,958 per person
￥283,958
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience
Reviewed on Oct 31, 2025
Swissotel - Chicago
Downtown Chicago
Price was ￥440,114, price is now ￥393,086 per person
￥393,086
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
Front desk and room service staff were great. Clean room great views
Reviewed on Oct 30, 2025
Top Romantic Illinois Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is ￥13,602 per night from Nov 17 to Nov 18
￥13,602
￥18,232 total
Nov 17 - Nov 18
includes taxes & fees
For a romantic stay, consider this boutique hotel, featuring a garden, jetted tubs, and in-room fireplaces. Couples will appreciate the romance packages and ...
8.4/10 Very Good! (1,306 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
Clean, comfortable, Hot water!
Reviewed on Oct 26, 2025
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, IL
The price is ￥24,006 per night from Nov 25 to Nov 26
￥24,006
￥28,181 total
Nov 25 - Nov 26
includes taxes & fees
Indulge in a romantic getaway at this upscale hotel, where you'll find a spa, in-room massages, and onsite dining. Couples will love the Frette Italian sheets ...
9.4/10 Exceptional! (3,370 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
Everything about this Hotel was top tier and prestigious. Highly recommended. Rooms were extremely clean, Staff super friendly and the Breakfast was delicious. You have to try the pancakes and French toast
Reviewed on Oct 27, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
The price is ￥16,739 per night from Nov 25 to Nov 26
￥16,739
￥23,468 total
Nov 25 - Nov 26
includes taxes & fees
You and your special someone are sure to love the
8.4/10 Very Good! (2,043 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
Everything was very good. Just as my previous stays have been
Reviewed on Oct 26, 2025
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.
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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.
