Diamond Vacations from $438

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The Latest Diamond vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Their motto “natural and happy” really fits. The staff were pleasant and helpful and the natural touches like natural soaps and cucumber mint infused water made it a comfortable, happy place to stay. An oasis in a hot city.

Reviewed on Jul 4, 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,755 reviews)
beautiful hotel, friendly and helpful staff.

Reviewed on Jul 2, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The rooftop…which is mostly enclosed with lots of windows?

Reviewed on Jul 4, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
The staff hospitality was incredible 💖

Reviewed on Jul 2, 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,564 reviews)
Polite staff. Convenient location. Clean hotel.

Reviewed on Jul 5, 2025

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Diamond Hotel Deals

aruba- la cabana beach resort and casino
aruba- la cabana beach resort and casino
Diamond
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aruba- la cabana beach resort and casino
Red Roof Inn Chicago - Joliet
Red Roof Inn Chicago - Joliet
2 out of 5
1750 Mcdonough St, Joliet, IL
Fully refundableReserve now, pay when you stay
$46 nightly
The price is $53 total per night from Jul 8 to Jul 9
$53 total
Jul 8 - Jul 9
Total includes taxes and fees
6.6/10 (1,003 reviews)
"You get what you pay for, can’t complain too much for the price. Great deal if you need to crash somewhere for the night"

Reviewed on Jul 2, 2025

Red Roof Inn Chicago - Joliet
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
$65 nightly
The price is $75 total per night from Jul 21 to Jul 22
$75 total
Jul 21 - Jul 22
Total includes taxes and fees
8/10 Very Good! (582 reviews)
"Clean"

Reviewed on Jul 3, 2025

Super 8 by Wyndham Joliet
See all 68 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.

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 $438 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.