Diamond Vacations from $389
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
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The Latest Diamond vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$544
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Only the wall outlet near the beds didn't work ...just that...everything was great !! Excelent hotel
Reviewed on Sep 21, 2026
Diamond Hotel Deals
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
$85 nightly
$99 total
Oct 6 - Oct 7
Total with taxes and fees
8.4/10 Very Good! (1,065 reviews)
"Great description, rooms were nice, the only critique I have was the hot tub was not hot"
Reviewed on Sep 19, 2026
Red Roof Inn Chicago - Joliet
1750 Mcdonough St Joliet IL
Fully refundableReserve now, pay when you stay
$55 nightly
$63 total
Sep 27 - Sep 28
Total with taxes and fees
6.8/10 (1,006 reviews)
"The room was ok for the price. It was a place to sleep right off the interstate. The room could use some TLC, but it was adequate. I got what I paid for. Not great, but served its purpose. I wasn't there for the amenities, I just needed a place to sleep. It looks kind of sketchy, but didn't feel ..."
Reviewed on Sep 20, 2026
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
151 N Joliet St Joliet IL
$102 nightly
$119 total
Oct 21 - Oct 22
Total with taxes and 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.
Find the Best Diamond Vacation Packages
Diamond Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,500 |
Top Sights | Heidecke Lake State Fish and Wildlife Area, Gebhard Woods State Park and William G. Stratton State Park |
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Frequently asked questions
How much does a Diamond vacation package cost?
You'll find cheap prices from $389 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?
You can typically find lower rates and greater availability in December, January and February. Take a look at our cheap Diamond vacation packages and you could land some excellent off-season deals.
How many days is enough for Diamond?
The ideal duration for your Diamond vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to tick off all the main attractions and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Diamond vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Diamond break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
