Illinois Romantic Vacations
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Top Romantic vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥373,801, price is now ￥244,202 per person
￥244,202
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥414,058, price is now ￥303,984 per person
￥303,984
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
It didn’t come with breakfast. The light in the bathroom was a little bit low. There was no comfortable chair in the room and no coffee in the room. Other than that the room was great and for the price and location. It’s good for downtown Chicago. Staff was amazing!
Reviewed on Apr 12, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥434,144, price is now ￥325,103 per person
￥325,103
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Fantastic hotel in a great central location with helpful staff - what more could we ask for?!
Reviewed on Apr 11, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥411,626, price is now ￥322,312 per person
￥322,312
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Darnell was the absolute BEST!!
Reviewed on Apr 11, 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was ￥496,508, price is now ￥388,984 per person
￥388,984
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
This is the best hotel on Michigan Avenue. Access to Nordstrom without leaving the building. Great views, food, very clean and smells amazing!
Reviewed on Apr 11, 2026
5* Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥373,801, price is now ￥244,202 per person
￥244,202
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥518,290, price is now ￥418,698 per person
￥418,698
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥384,943, price is now ￥336,512 per person
￥336,512
per person
Jun 22 - Jun 24
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
3 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥414,058, price is now ￥303,984 per person
￥303,984
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
It didn’t come with breakfast. The light in the bathroom was a little bit low. There was no comfortable chair in the room and no coffee in the room. Other than that the room was great and for the price and location. It’s good for downtown Chicago. Staff was amazing!
Reviewed on Apr 12, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥434,144, price is now ￥325,103 per person
￥325,103
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Fantastic hotel in a great central location with helpful staff - what more could we ask for?!
Reviewed on Apr 11, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥411,626, price is now ￥322,312 per person
￥322,312
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Darnell was the absolute BEST!!
Reviewed on Apr 11, 2026
4 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was ￥266,464, price is now ￥175,856 per person
￥175,856
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Fantastic hotel in a great central location with helpful staff - what more could we ask for?!
Reviewed on Apr 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥373,801, price is now ￥244,202 per person
￥244,202
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥268,724, price is now ￥177,272 per person
￥177,272
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.
Reviewed on Apr 6, 2026
Top Romantic Illinois Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
The price is ￥16,198 per night from Apr 13 to Apr 14
￥16,198
￥21,148 total
Apr 13 - Apr 14
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! (1,466 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
Yes
Reviewed on Apr 12, 2026
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
The price is ￥40,356 per night from Apr 26 to Apr 27
￥40,356
￥52,049 total
Apr 26 - Apr 27
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! (3,654 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
This hotel far exceeded our expectations! The location was perfect! Parking-easy. Hotel was beautiful and our king suite was wonderful to come back from walking the city to relax. The rooftop had spectacular views and the staff was friendly and helpful. We couldn’t have asked for a better ...
Reviewed on Apr 11, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is ￥25,337 per night from May 9 to May 10
￥25,337
￥33,727 total
May 9 - May 10
includes taxes & fees
You and your special someone are sure to love the
8.6/10 Excellent! (2,382 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
Staff was very friendly.
Reviewed on Apr 12, 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.
