
Plainfield Vacations from ¥168,448
Book a Hotel + Flight or Car together to unlock savings
Photo by Jeff Hancock
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Plainfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ¥214,272, price is now ¥168,448 per person
¥168,448
per person
Jan 25 - Jan 30
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was ¥371,466, price is now ¥260,622 per person
¥260,622
per person
Dec 23 - Dec 27
found 21 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥326,377, price is now ¥233,804 per person
¥233,804
per person
Jan 25 - Jan 30
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.
Reviewed on Nov 14, 2025

Level Chicago – Old Town
Downtown Chicago
Price was ¥250,082, price is now ¥191,525 per person
¥191,525
per person
Jan 25 - Jan 30
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025

Pendry Chicago
Downtown Chicago
Price was ¥224,775, price is now ¥174,228 per person
¥174,228
per person
Jan 25 - Jan 30
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Staff was our favorite part! Very very professional and friendly
Reviewed on Nov 14, 2025
Find the Best Plainfield Vacation Packages
Plainfield Hotel Deals

Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is ¥10,509 per night from Dec 16 to Dec 17
¥10,509
¥11,663 total
Dec 16 - Dec 17
includes taxes & fees
7/10 Good! (1,319 reviews)
i like that place
Reviewed on Nov 13, 2025

Motel 6 Naperville, IL
1585 Naperville Wheaton Road Naperville IL
Fully refundable
The price is ¥7,649 per night from Nov 24 to Nov 25
¥7,649
¥8,527 total
Nov 24 - Nov 25
includes taxes & fees
7.8/10 Good! (1,114 reviews)
Staff was excellent
Reviewed on Nov 11, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is ¥11,467 per night from Nov 18 to Nov 19
¥11,467
¥12,726 total
Nov 18 - Nov 19
includes taxes & fees
8.8/10 Excellent! (2,388 reviews)
The room and staff!
Reviewed on Nov 17, 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.
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
