Downtown Vacations from ￥349,994
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The Latest Downtown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥659,915, price is now ￥426,058 per person
￥426,058
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Good breakfast, excellent service, unfortunately, they don't have microwave service to heat food
Reviewed on Mar 13, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥560,889, price is now ￥424,265 per person
￥424,265
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on Mar 13, 2026
Hilton Chicago
Downtown Chicago
Price was ￥605,910, price is now ￥499,852 per person
￥499,852
per person
May 28 - Jun 1
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,658 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on Mar 12, 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 Michigan Maritime Museum and North Beach.
Downtown Hotel Deals
Old Harbor Inn
515 Williams Street South Haven MI
Fully refundableReserve now, pay when you stay
The price is ￥15,357 per night from Mar 16 to Mar 17
￥15,357
￥17,046 total
Mar 16 - Mar 17
includes taxes & fees
9.4/10 Exceptional! (690 reviews)
Wow, this place was beautiful. Its everything the pictures show and MORE! I cant wait to come back during open season!
Reviewed on Mar 10, 2026
Historic Hotel Nichols
201 Center St South Haven MI
The price is ￥21,505 per night from Mar 15 to Mar 16
￥21,505
￥23,871 total
Mar 15 - Mar 16
includes taxes & fees
9.8/10 Exceptional! (134 reviews)
Everything was perfect! The staff was the best ever!!! They were very welcoming and made sure we were very informed. The breakfast they made the next day was perfect!!
Reviewed on Mar 5, 2026
The Black Pearl: industrial condo sleeps 6, full size kitchen & scenic views!
South Haven MI
10/10 Exceptional! (126 reviews)
great place. really nice. as advertised. would rent again
Reviewed on Mar 8, 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.
Discover the most popular places to visit in Downtown
Michigan Maritime Museum
4/5(5 reviews)
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.