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 ￥274,580, price is now ￥221,432 per person
￥221,432
per person
Mar 16 - Mar 20
found 10 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 ￥581,636, price is now ￥458,678 per person
￥458,678
per person
Mar 22 - Mar 28
found 13 hours ago
Roundtrip flight included
Tokushima (TKS) 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 ￥303,137, price is now ￥250,502 per person
￥250,502
per person
Mar 17 - Mar 20
found 17 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
Palmer House a Hilton Hotel
Downtown Chicago
Price was ￥260,436, price is now ￥227,943 per person
￥227,943
per person
Mar 16 - Mar 20
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,059 reviews)
Room was very clean and staff was great
Reviewed on Jan 6, 2026
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 ￥303,137, price is now ￥250,502 per person
￥250,502
per person
Mar 17 - Mar 20
found 17 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
The Peninsula Chicago
Downtown Chicago
Price was ￥581,636, price is now ￥458,678 per person
￥458,678
per person
Mar 22 - Mar 28
found 13 hours ago
Roundtrip flight included
Tokushima (TKS) 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
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 ￥231,572, price is now ￥209,288 per person
￥209,288
per person
Mar 17 - Mar 20
found 17 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥303,137, price is now ￥250,502 per person
￥250,502
per person
Mar 17 - Mar 20
found 17 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
4 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 ￥274,580, price is now ￥221,432 per person
￥221,432
per person
Mar 16 - Mar 20
found 10 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 10 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 10 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
Top Romantic Illinois Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
The price is ￥13,954 per night from Jan 12 to Jan 13
￥13,954
￥18,703 total
Jan 12 - Jan 13
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! (1,377 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
Privacy was excellent. The room was clean and the staff was very pleasant to talk with and answered all our questions.
Reviewed on Jan 6, 2026
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
The price is ￥21,703 per night from Jan 19 to Jan 20
￥21,703
￥25,478 total
Jan 19 - Jan 20
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! (3,497 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
Had great rooms was very happy with Alfie and how he answered all my questions and made sure I was happy and comfortable. Thank you Alfie for making my stay amazing.
Reviewed on Jan 7, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
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
You and your special someone are sure to love the
8.4/10 Very Good! (2,226 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
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.
More Vacation Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
