
Glenwood Vacations from ¥355,796
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The Latest Glenwood Vacation Packages
Price found within the past 48 hours. Click for updated prices.



Silversmith Hotel Chicago Downtown
Downtown Chicago
Price was ¥675,684, price is now ¥495,208 per person
¥495,208
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,325 reviews)
The hotel is comfortable and well-maintained. It is located at the base of an L train. Stop that whisks passengers to Midway airport in 30 minutes. The location also gives access to Grant Park, State Street and the miracle mile. Rooms are large, comfortable and clean.
Reviewed on Aug 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥582,115, price is now ¥428,977 per person
¥428,977
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Overall I had a very good stay over there. My one complaint was there wasn't a microwave in the room.
Reviewed on Aug 3, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥591,690, price is now ¥440,253 per person
¥440,253
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,732 reviews)
There was no early check-in unfortunately. All staff were very friendly and helpful. Really grateful for the sturdy umbrellas in the room.
Reviewed on Aug 3, 2026
Find the Best Glenwood Vacation Packages
Glenwood Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is ¥20,609 per night from Aug 13 to Aug 14
¥20,609
¥25,766 total
Aug 13 - Aug 14
includes taxes & fees

Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
The price is ¥31,307 per night from Aug 9 to Aug 10
¥31,307
¥36,751 total
Aug 9 - Aug 10
includes taxes & fees
7/10 Good! (1,007 reviews)
"My room was clean, bed was clean. Very pleased with the room. Only down part was the drain was clogged in the shower. Staff was kind, the hallways were dirty and had a funky smell but didn’t smell it once I went into my room. Was visiting from out of state and was informed by more than one person ..."
Reviewed on Aug 3, 2026

Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥15,525 per night from Aug 25 to Aug 26
¥15,525
¥18,241 total
Aug 25 - Aug 26
includes taxes & fees
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
