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
- Rest easyPlan, book, and manage your trip all in one place
Top Honeymoon vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Price was ￥198,460, price is now ￥160,435 per person
￥160,435
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,059 reviews)
Beautiful hotel! Perfect for a holiday staycation!
Reviewed on Dec 16, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥355,415, price is now ￥261,880 per person
￥261,880
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing
Reviewed on Dec 16, 2025
Pendry Chicago
Downtown Chicago
Price was ￥208,927, price is now ￥161,814 per person
￥161,814
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Excellent location to stay in the heart of the city.
Reviewed on Dec 17, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥355,275, price is now ￥295,737 per person
￥295,737
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
5* Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥355,415, price is now ￥261,880 per person
￥261,880
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing
Reviewed on Dec 16, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥393,998, price is now ￥304,081 per person
￥304,081
per person
Mar 2 - Mar 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥420,340, price is now ￥330,843 per person
￥330,843
per person
Mar 2 - Mar 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
3 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was ￥279,759, price is now ￥255,331 per person
￥255,331
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Excellent location to stay in the heart of the city.
Reviewed on Dec 17, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥355,275, price is now ￥295,737 per person
￥295,737
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥356,185, price is now ￥312,830 per person
￥312,830
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing
Reviewed on Dec 16, 2025
4 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥393,998, price is now ￥304,081 per person
￥304,081
per person
Mar 2 - Mar 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥420,340, price is now ￥330,843 per person
￥330,843
per person
Mar 2 - Mar 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
Top Honeymoon Chicago Hotels
Eurostars Magnificent Mile
660 North State Street Chicago IL
Book a stay at this 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! (3,156 reviews)
staff was very helpful & friendly, hotel was clean.
Reviewed on Dec 14, 2025
The Wade
644 N Lake Shore Dr Chicago IL
Book a stay at this 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! (1,521 reviews)
Yes
Reviewed on Dec 15, 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! (1,002 reviews)
nice clean room
Reviewed on Dec 9, 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.
