Chicago Honeymoon Vacations
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Top Honeymoon vacation packages 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
The Wade
Downtown Chicago
Price was ￥442,434, price is now ￥337,288 per person
￥337,288
per person
May 13 - May 18
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Enjoyed our stay. Views were amazing and location convenient.
Reviewed on Mar 26, 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
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥695,660, price is now ￥574,362 per person
￥574,362
per person
May 13 - May 18
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
Pendry Chicago
Downtown Chicago
Price was ￥567,514, price is now ￥476,067 per person
￥476,067
per person
May 13 - May 18
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back.
Reviewed on Mar 23, 2026
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 ￥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
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥695,660, price is now ￥574,362 per person
￥574,362
per person
May 13 - May 18
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 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 20 hours 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 Honeymoon 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 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
This was the ideal room for a family! The king spa suite was everything we wanted it to be. It was clean and spacious. The pool was small but great for getting some energy out of the kids! Great view of the city too. Perfect location to walk wherever with a million things within a few minutes walk. Staff was nice and we will return!
Reviewed on Mar 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥434,357, price is now ￥350,134 per person
￥350,134
per person
May 14 - May 17
found 10 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 ￥367,785, price is now ￥325,429 per person
￥325,429
per person
May 13 - May 16
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Good staff, clean room,m. I didn’t like that the bathroom was almost see through from the other side of the room, you can’t see the person inside the bathroom but you can see the cilhouette
Reviewed on Mar 26, 2026
4 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 ￥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)
Good staff, clean room,m. I didn’t like that the bathroom was almost see through from the other side of the room, you can’t see the person inside the bathroom but you can see the cilhouette
Reviewed on Mar 26, 2026
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 ...
9/10 Wonderful! (3,330 reviews)
Yes
Reviewed on Mar 26, 2026
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! (1,753 reviews)
Enjoyed our stay. Views were amazing and location convenient.
Reviewed on Mar 26, 2026
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! (1,001 reviews)
Absolutely yes clean room, staff was great so was the bar and breakfast.
Reviewed on Mar 26, 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.
