West Side Adults Only Vacations
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Top Adults Only vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was ￥358,742, price is now ￥285,163 per person
￥285,163
per person
Jun 26 - Jun 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
The room is really a small apartment. Fulton Market area is quite energetic. Quite nice.
Reviewed on Apr 12, 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was ￥496,508, price is now ￥388,984 per person
￥388,984
per person
May 14 - May 17
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
This is the best hotel on Michigan Avenue. Access to Nordstrom without leaving the building. Great views, food, very clean and smells amazing!
Reviewed on Apr 11, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥661,897, price is now ￥521,872 per person
￥521,872
per person
Jun 1 - Jun 8
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Price was ￥391,785, price is now ￥312,789 per person
￥312,789
per person
May 14 - May 17
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
Everything was perfect. They even had free snacks and wines in the afternoon
Reviewed on Apr 12, 2026
5* Adults Only vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥184,121, price is now ￥127,349 per person
￥127,349
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥518,290, price is now ￥418,698 per person
￥418,698
per person
May 14 - May 17
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥384,943, price is now ￥336,512 per person
￥336,512
per person
Jun 22 - Jun 24
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
3 Night Adults Only vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Price was ￥391,785, price is now ￥312,789 per person
￥312,789
per person
May 14 - May 17
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
Everything was perfect. They even had free snacks and wines in the afternoon
Reviewed on Apr 12, 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was ￥496,508, price is now ￥388,984 per person
￥388,984
per person
May 14 - May 17
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
This is the best hotel on Michigan Avenue. Access to Nordstrom without leaving the building. Great views, food, very clean and smells amazing!
Reviewed on Apr 11, 2026
4 Night Adults Only vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥365,491, price is now ￥275,432 per person
￥275,432
per person
Jun 26 - Jun 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Fabulous hotel in the BEST location. We loved the rooftop bar, exceptional breakfast buffet, and cleanliness of hotel. I would recommend highly and look forward to staying there again.
Reviewed on Apr 12, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥479,394, price is now ￥368,196 per person
￥368,196
per person
Jun 26 - Jun 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥358,742, price is now ￥285,163 per person
￥285,163
per person
Jun 26 - Jun 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
The room is really a small apartment. Fulton Market area is quite energetic. Quite nice.
Reviewed on Apr 12, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
