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 ￥487,896, price is now ￥398,236 per person
￥398,236
per person
Jun 8 - Jun 12
found 1 day 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)
The hotel staff was the best, I always love my stay here! My only complaint is there are no microwaves in the rooms :(
Reviewed on Mar 26, 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 Chicago
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 1 day 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 ￥555,302, price is now ￥474,136 per person
￥474,136
per person
May 18 - May 22
found 1 hour ago
Roundtrip non-stop flight included
Osaka (OSA) 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 Chicago
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 13 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Great location, friendly staff, clean and very comfortable rooms. There are restaurants, shopping, grocery stores etc all within walking distance.
Reviewed on Mar 26, 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
found 2 hours ago
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 13 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The hotel staff was the best, I always love my stay here! My only complaint is there are no microwaves in the rooms :(
Reviewed on Mar 26, 2026
4 Night Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥352,144, price is now ￥297,676 per person
￥297,676
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 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 1 day 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 ￥378,785, price is now ￥320,363 per person
￥320,363
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The hotel staff was the best, I always love my stay here! My only complaint is there are no microwaves in the rooms :(
Reviewed on Mar 26, 2026
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 ...
8.6/10 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
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
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
