Illinois Romantic Vacations
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Top Romantic vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
Price was ￥131,836, price is now ￥112,018 per person
￥112,018
per person
Jun 12 - Jun 14
found 19 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.2/10 Very Good! (1,411 reviews)
A short walk to Lake Michigan, Magnificant Mile in a peaceful neighbourhood. The gallery in the basement is also worth checking out with rich cultural history. Architecture is great too！
Reviewed on May 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥619,042, price is now ￥484,597 per person
￥484,597
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor
Very disappointing
Reviewed on May 10, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥717,300, price is now ￥562,296 per person
￥562,296
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Loved the location. Loved the property , staff, amenities, and service. I did not live the brutal Chicago cold. Four below is just hateful cold weather. Want to return this summer or fall to enjoy the area. Excellent property. Definitely recommend you stay if in Chicago.
Reviewed on May 10, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥689,825, price is now ￥554,748 per person
￥554,748
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was ￥484,921, price is now ￥412,988 per person
￥412,988
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,442 reviews)
The room was very comfortable, clean, and well maintained. I had a relaxing stay and really appreciated the quiet and pleasant environment. The bed was comfortable, the space felt cozy, and everything in the room was easy to use. The property also had a very nice atmosphere, making it a great place to rest after a day of travel.
The staff were friendly and helpful, and the overall experience was smooth from check-in to check-out. The location and surroundings were also very enjoyable. I would definitely recommend this place to other travelers and would be happy to stay here again in the future
Reviewed on May 7, 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 ￥619,042, price is now ￥484,597 per person
￥484,597
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor
Very disappointing
Reviewed on May 10, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥717,300, price is now ￥562,296 per person
￥562,296
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Loved the location. Loved the property , staff, amenities, and service. I did not live the brutal Chicago cold. Four below is just hateful cold weather. Want to return this summer or fall to enjoy the area. Excellent property. Definitely recommend you stay if in Chicago.
Reviewed on May 10, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥689,825, price is now ￥554,748 per person
￥554,748
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
4 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥437,988, price is now ￥354,950 per person
￥354,950
per person
Jun 16 - Jun 20
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
The view is fantastic. You can see the Chicago river on one side, abd skyscraper on tge other side. The small items that the hotel provides, makes the stay, pleasant and homely.
Reviewed on May 10, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥462,078, price is now ￥387,046 per person
￥387,046
per person
Jun 16 - Jun 20
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great property and location!
Reviewed on May 8, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥453,026, price is now ￥384,589 per person
￥384,589
per person
Jul 26 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Top Romantic Illinois Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
The price is ￥17,908 per night from Jun 7 to Jun 8
￥17,908
￥22,896 total
Jun 7 - Jun 8
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 ...
8.6/10 Excellent! (1,505 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
Room had broken glass from previous stay under bed when we took are used bedding off from are night before leaving we found four other fitted sheets understand it not sure if they were used an jus put a new one on ares but there was also rose peddles we never used that fell out or the sheets we took ...
Reviewed on May 10, 2026
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
The price is ￥29,421 per night from May 25 to May 26
￥29,421
￥39,580 total
May 25 - May 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! (3,713 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
Very good breakfast
Reviewed on May 10, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is ￥27,262 per night from May 25 to May 26
￥27,262
￥37,070 total
May 25 - May 26
includes taxes & fees
You and your special someone are sure to love the
8.6/10 Excellent! (2,436 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
Great staff, food great, room great will return again.
Reviewed on May 9, 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.
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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.
