
Gilberts Vacations from ¥197,570
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The Latest Gilberts Vacation Packages
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥249,442, price is now ¥197,570 per person
¥197,570
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025

Pendry Chicago
Downtown Chicago
Price was ¥287,032, price is now ¥216,994 per person
¥216,994
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025

Level Chicago – Old Town
Downtown Chicago
Price was ¥283,128, price is now ¥217,668 per person
¥217,668
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue.
However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).
Reviewed on Oct 22, 2025

The Emily Hotel
Downtown Chicago
Price was ¥301,025, price is now ¥237,066 per person
¥237,066
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!
Reviewed on Oct 22, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥278,855, price is now ¥224,056 per person
¥224,056
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
This hotel was nearly perfect! Great staff. Great location. Clean. My only complaint was the ice machine was broken on our floor. We reported it to staff 3 separate occasions and it wasn’t fixed in the 5 days we were there. Hotel is located on a busy street so there is some noise but if that Doesn't bother you… this is perfect. Very walkable location! The staff there are fantastic. From the moment you walk in until the moment you leave. They understand the assignment. Highly recommend.
Reviewed on Oct 21, 2025
Find the Best Gilberts Vacation Packages
Gilberts Hotel Deals

Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ¥10,330 per night from Oct 28 to Oct 29
¥10,330
¥11,879 total
Oct 28 - Oct 29
includes taxes & fees
6.6/10 (1,042 reviews)
The price for the hotel was amazing, great value, and overall I was well pleased with the hotel and the room. Also, the staff both in the evening and morning were 5 stars plus, very friendly and attentive. What was a concern to me was while walking in the hallways the wallpaper appeared worn out ...
Reviewed on Oct 16, 2025

Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ¥12,138 per night from Oct 30 to Oct 31
¥12,138
¥13,956 total
Oct 30 - Oct 31
includes taxes & fees
7/10 Good! (963 reviews)
It was good, we just didn't have a remote for the television. When we did get one, it wasn't programmed
Reviewed on Oct 13, 2025

Eaglewood Resort and Spa
1401 Nordic Rd, Itasca, IL
Fully refundableReserve now, pay when you stay
The price is ¥15,587 per night from Nov 9 to Nov 10
¥15,587
¥20,640 total
Nov 9 - Nov 10
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
Room is spacious, overall clean but a makeup remove wipe was left in the bathroom. Rooms are not sound proof, I can clear hear people talking in the corridor and the room next to me. Service is good, staff are very nice. Water in the pool is clear but the bottom is dirty. Self made waffle in breakfast ...
Reviewed on Oct 15, 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.
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