Diamond Vacations from ￥248,500

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The Latest Diamond Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥343,557, price is now ￥248,500 per person
￥248,500
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on Aug 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥353,710, price is now ￥268,396 per person
￥268,396
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
The place was in a great location, close to everything. I was traveling alone and felt very comfortable. The roof bar was gorgeous but the service was just ok up there.

Reviewed on Aug 28, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥358,844, price is now ￥278,143 per person
￥278,143
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.

Reviewed on Aug 25, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was ￥323,910, price is now ￥251,450 per person
￥251,450
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
The bed and pillows were amazing, I’ve never had a better nights sleep. I would live to know if and where I can purchase the same products!

Reviewed on Aug 28, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥409,499, price is now ￥319,112 per person
￥319,112
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
The Hotel is very convenient, but needs updating. The bathrooms are old, etc. The staff was very friendly and the dining options are excellent and very convenient given you’re in the middle of the airport.

Reviewed on Aug 26, 2025

Find the Best Diamond Vacation Packages

Diamond Hotel Deals

aruba- la cabana beach resort and casino

aruba- la cabana beach resort and casino

Diamond
Get rates
aruba- la cabana beach resort and casino
Super 8 by Wyndham Joliet

Super 8 by Wyndham Joliet

2 out of 5
1806 McDonough St, Joliet, IL
Fully refundableReserve now, pay when you stay
The price is ￥11,248 per night from Sep 7 to Sep 8
￥11,248
￥13,045 total
Sep 7 - Sep 8
includes taxes & fees
Super 8 by Wyndham Joliet
Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

2.5 out of 5
101 McDonald Avenue, Joliet, IL
Fully refundableReserve now, pay when you stay
The price is ￥11,796 per night from Sep 1 to Sep 2
￥11,796
￥13,681 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
Nice place
"Nice and clean, with exceptional service from front desk staff."

Reviewed on Aug 22, 2025

Wingate by Wyndham - Joliet
See all 72 properties in Diamond
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

How much does a Diamond vacation package cost?
You'll find cheap prices from ￥248,500 on Expedia for your Diamond escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Diamond costs.
What are the cheapest months to go to Diamond?
If you're looking to snag a cheap Diamond vacation package, consider visiting in January, February and March. You'll usually find better prices on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Diamond?
With a well-organized travel plan, you can easily hit the main Diamond sights in a few days. But if you prefer to discover hidden spots or take day trips, consider booking your Diamond vacation for longer.
How to find the best Diamond package deals?
Start your search for a Diamond package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Diamond package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Diamond getaway off to a flying start.
Is it cheaper to book a Diamond vacation as a package?
You can enjoy significant savings on your next Diamond escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Diamond?
If you're considering an impromptu Diamond vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Diamond?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to visit Diamond.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Diamond.
  3. Decide how long to go for: Now that you know more about Diamond, you can figure out the perfect length of your break. Create a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Diamond vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.