Chicago Romantic Vacations
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Top Romantic vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
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 17 hours 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
Swissotel - Chicago
Downtown Chicago
Price was ￥465,548, price is now ￥393,530 per person
￥393,530
per person
Nov 30 - Dec 5
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
Easy check in and the property is modern with all required facilities and very clean with great service.
Reviewed on Oct 29, 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 17 hours 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 Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
3 Night Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥237,656, price is now ￥220,140 per person
￥220,140
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
Easy check in and the property is modern with all required facilities and very clean with great service.
Reviewed on Oct 29, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥335,652, price is now ￥281,290 per person
￥281,290
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
4 Night Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was ￥260,574, price is now ￥233,896 per person
￥233,896
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,496 reviews)
Very well located, great bed and shower.
Reviewed on Oct 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
Top Romantic Chicago Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
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
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
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
