Chicago Honeymoon Vacations
Book a Honeymoon Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Honeymoon vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Price was ￥199,259, price is now ￥183,468 per person
￥183,468
per person
Dec 25 - Dec 28
found 14 hours ago
Roundtrip non-stop flight included
Naha (OKA) to Chicago (ORD)
8.4/10 Very Good! (1,736 reviews)
The room was spotless...I was there for the tub which did not disappoint... It was clean deep and relaxing.
Reviewed on Oct 30, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥340,000, price is now ￥284,970 per person
￥284,970
per person
Jan 17 - Jan 21
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience
Reviewed on Oct 31, 2025
Omni Chicago Hotel
Downtown Chicago
Price was ￥269,080, price is now ￥248,740 per person
￥248,740
per person
Jan 17 - Jan 21
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,583 reviews)
Staff was really welcoming! Valet staff were very helpful! The suite was okay: bed was really comfortable but bathroom is slightly dated with no ventilation…
Reviewed on Oct 30, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥253,204, price is now ￥234,470 per person
￥234,470
per person
Jan 17 - Jan 21
found 5 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* Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥340,000, price is now ￥284,970 per person
￥284,970
per person
Jan 17 - Jan 21
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience
Reviewed on Oct 31, 2025
3 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥186,414, price is now ￥173,082 per person
￥173,082
per person
Dec 25 - Dec 28
found 14 hours ago
Roundtrip non-stop flight included
Naha (OKA) to Chicago (ORD)
8.2/10 Very Good! (2,273 reviews)
It was my first time in Chicago plus I was travelling with my two service dogs and I couldn't have chosen a better hotel option.
The room and experience was very reminiscent of Fairmont (I usually stay at a Fairmont but I wasn't able to secure the room needed for the dates) but with a considerable cost savings so I definitely chose well.
Will absolutely recommend The Felix to anyone I know travelling to Chicago as a solid hotel option.
Reviewed on Oct 31, 2025
Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Price was ￥199,259, price is now ￥183,468 per person
￥183,468
per person
Dec 25 - Dec 28
found 14 hours ago
Roundtrip non-stop flight included
Naha (OKA) to Chicago (ORD)
8.4/10 Very Good! (1,736 reviews)
The room was spotless...I was there for the tub which did not disappoint... It was clean deep and relaxing.
Reviewed on Oct 30, 2025
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥205,774, price is now ￥191,340 per person
￥191,340
per person
Dec 25 - Dec 28
found 14 hours ago
Roundtrip non-stop flight included
Naha (OKA) to Chicago (ORD)
9/10 Wonderful! (3,081 reviews)
The location was so spectacular. The staff was courteous and knowledgeable. I stayed in the panoramic room and it gave me exactly what I was expecting which was nice views. I would definitely stay here again.
Reviewed on Oct 30, 2025
4 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ￥269,080, price is now ￥248,740 per person
￥248,740
per person
Jan 17 - Jan 21
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,583 reviews)
Staff was really welcoming! Valet staff were very helpful! The suite was okay: bed was really comfortable but bathroom is slightly dated with no ventilation…
Reviewed on Oct 30, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥340,000, price is now ￥284,970 per person
￥284,970
per person
Jan 17 - Jan 21
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience
Reviewed on Oct 31, 2025
Top Honeymoon Chicago Hotels
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (3,087 reviews)
Clean room Staff nice I just didn't like the fact that you had to pay for the snacks and drinks in the room, and the room is already a nice price. But still very beautiful room
Reviewed on Oct 27, 2025
The Wade
644 N Lake Shore Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,396 reviews)
Best place
Reviewed on Oct 28, 2025
Hyatt Lodge Oak Brook Chicago
2815 Jorie Blvd, Oak Brook, IL
Book a stay at this spa hotel in Oak Brook. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,005 reviews)
Loved the forest setting
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.
