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
Price was ￥487,896, price is now ￥398,236 per person
￥398,236
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit.
We will be back in near future for surr!
Reviewed on Mar 24, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥541,318, price is now ￥398,727 per person
￥398,727
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean!
Reviewed on Mar 25, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥549,989, price is now ￥434,752 per person
￥434,752
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans!
The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too!
The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well!
All and all it’s a wonderful place to experience!!!!🍍
Reviewed on Mar 18, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥515,609, price is now ￥421,434 per person
￥421,434
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Refused to park my challenger for valet
Reviewed on Mar 25, 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 ￥487,896, price is now ￥398,236 per person
￥398,236
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit.
We will be back in near future for surr!
Reviewed on Mar 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥533,182, price is now ￥490,020 per person
￥490,020
per person
Jun 12 - Jun 15
just found
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Wonderful, from the property to the staff, the food and the amenities. Will be staying again any time I travel to Chicago.
Reviewed on Mar 25, 2026
3 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥353,290, price is now ￥298,874 per person
￥298,874
per person
May 13 - May 16
found 11 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Great Staff ! Stay was very comfortable and the hotel has a great location near plenty of restaurants
Reviewed on Mar 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥495,293, price is now ￥416,744 per person
￥416,744
per person
Jun 12 - Jun 15
just found
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit.
We will be back in near future for surr!
Reviewed on Mar 24, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥367,785, price is now ￥325,429 per person
￥325,429
per person
May 13 - May 16
found 11 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean!
Reviewed on Mar 25, 2026
4 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥378,785, price is now ￥320,363 per person
￥320,363
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean!
Reviewed on Mar 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥487,896, price is now ￥398,236 per person
￥398,236
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit.
We will be back in near future for surr!
Reviewed on Mar 24, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥387,877, price is now ￥345,768 per person
￥345,768
per person
Apr 29 - May 3
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Refused to park my challenger for valet
Reviewed on Mar 25, 2026
Top Romantic Illinois Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
The price is ￥18,011 per night from Apr 15 to Apr 16
￥18,011
￥23,073 total
Apr 15 - Apr 16
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! (1,445 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
It was an amazing out of the way hotel for a discreet hookup! I wasn’t there for that but I would recommend it if that is what you are looking for.
Reviewed on Mar 23, 2026
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
The price is ￥40,209 per night from Apr 6 to Apr 7
￥40,209
￥47,201 total
Apr 6 - Apr 7
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! (3,621 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
If you want to be central to downtown Chicago this is the hotel. I really enjoyed my stay. Great rooftop bar and 2 attached restaurants you can go to if you don't want to travel outside the hotel. However, the hotel pillows are trash. Bring your own pillow if you dont want a stiff neck
Reviewed on Mar 25, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is ￥26,140 per night from Apr 5 to Apr 6
￥26,140
￥34,671 total
Apr 5 - Apr 6
includes taxes & fees
You and your special someone are sure to love the
8.6/10 Excellent! (2,338 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
Gorgeous historical location with lots of amenities and attentive staff. Really look forward to my next visit
Reviewed on Mar 24, 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.
