Diamond Vacations from ￥85,200

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    Save up to ￥109,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Diamond Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was ￥120,108, price is now ￥85,200 per person
￥85,200
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,343 reviews)
Great hotel

Reviewed on Jul 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥177,007, price is now ￥114,218 per person
￥114,218
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
salty breakfast

Reviewed on Jul 15, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥171,429, price is now ￥122,864 per person
￥122,864
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
All around amazing!

Reviewed on Jul 13, 2026

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥123,568, price is now ￥89,804 per person
￥89,804
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (2,618 reviews)
Wonderful staff. Very helpful and courteous. Excellent location - close to theater shows, Riverwalk and shopping downtown and lake shore. Felt very safe walking at night and the security on site. The waitstaff and food were excellent - arrived one night at 9:45 pm and within five minutes had a delicious meal! Would definitely stay there again! Bed was super comfy!!!

Reviewed on Jul 15, 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥127,701, price is now ￥96,893 per person
￥96,893
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,270 reviews)
The facilities are old, the room is not clean, the bedding smells of sweat, the pillow also has yellow marks, and there is still the hair of the previous guest on the washstand.

Reviewed on Jul 15, 2026

Find the Best Diamond Vacation Packages

Diamond Hotel Deals

Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

3 out of 5
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is ￥14,204 per night from Aug 6 to Aug 7
￥14,204
￥16,473 total
Aug 6 - Aug 7
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"just coffee no breakfast"

Reviewed on Jul 13, 2026

Wingate by Wyndham - Joliet
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
151 N Joliet St Joliet IL
The price is ￥10,375 per night from Aug 13 to Aug 14
￥10,375
￥14,856 total
Aug 13 - Aug 14
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"It's"

Reviewed on Jul 14, 2026

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Best Western Joliet Inn & Suites

Best Western Joliet Inn & Suites

2.5 out of 5
4380 Enterprise Drive Joliet IL
Fully refundableReserve now, pay when you stay
The price is ￥15,723 per night from Jul 28 to Jul 29
￥15,723
￥18,235 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very Good! (315 reviews)
"Property was well maintained, felt safe. Room was clean. Our room was on the first floor by the stairs and another entrance door, so it wasn't the quietest room unfortunately. Bed was comfortable."

Reviewed on Jul 9, 2026

Best Western Joliet Inn & Suites
See all 76 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 ￥85,200 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.

Explore a world of travel with Expedia

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