Downtown Vacations from ￥241,872
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Downtown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥450,632, price is now ￥332,884 per person
￥332,884
per person
Apr 1 - Apr 6
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
First time there. Staff was helpful and they provided excellent memorable service
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥329,524, price is now ￥245,333 per person
￥245,333
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Very clean room, friendly staff, wonderful breakfast!
Reviewed on Jan 22, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥407,761, price is now ￥319,483 per person
￥319,483
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room and the staff were wonderful!
Reviewed on Jan 22, 2026
Where to stay in Downtown
Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like North Beach and Michigan Maritime Museum.
Downtown Hotel Deals
Old Harbor Inn
515 Williams Street South Haven MI
Fully refundableReserve now, pay when you stay
The price is ￥14,631 per night from Jan 25 to Jan 26
￥14,631
￥16,241 total
Jan 25 - Jan 26
includes taxes & fees
9.4/10 Exceptional! (683 reviews)
Super clean, super friendly, super welcoming!
Reviewed on Jan 13, 2026
Historic Hotel Nichols
201 Center St South Haven MI
The price is ￥21,493 per night from Feb 8 to Feb 9
￥21,493
￥23,857 total
Feb 8 - Feb 9
includes taxes & fees
9.6/10 Exceptional! (131 reviews)
Second time staying here. Highly recommend A+
Reviewed on Jan 1, 2026
New Home with swim spa, theatre & game room. 1 block to town & close to beach.
South Haven MI
10/10 Exceptional! (196 reviews)
It was a wonderful place to spend a weekend with our family. Thank you
Reviewed on Dec 22, 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.
Discover the most popular places to visit in Downtown
Michigan Maritime Museum
You can spend an afternoon browsing the exhibits at Michigan Maritime Museum in South Haven. While you're in the area, stroll along the beautiful beaches.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.