Diamond Vacations from $420

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The Latest Diamond vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $724, price is now $420 per person
$420
per person
Nov 10 - Nov 16
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,002 reviews)
⭐️⭐️⭐️⭐️⭐️ Hotel Review: Hyatt Regency Deerfield I stayed at the Hyatt Regency Deerfield from Friday to Sunday, and it was truly a wonderful experience! The rooms were cozy, spotless, and very comfortable, making it easy to relax after a busy weekend. The staff was exceptional—warm, welcoming, and attentive in every interaction. The dining facility was excellent, with both the food and service exceeding expectations. After attending the John Legend concert, returning to the hotel felt like coming to a home away from home. Kudos to the entire team at Hyatt Regency Deerfield for making the stay memorable. I’ll definitely return and highly recommend this hotel!

Reviewed on Aug 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,298, price is now $646 per person
$646
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Had a great experience. Clean room, great rooftop bar, great breakfast!

Reviewed on Aug 25, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was $1,598, price is now $845 per person
$845
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug 21, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $864, price is now $512 per person
$512
per person
Oct 31 - Nov 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Right at the airport so it is convenient but it is old and needs updating

Reviewed on Aug 26, 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,255, price is now $756 per person
$756
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,020 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.

Reviewed on Aug 24, 2025

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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
$72 nightly
The price is $84 total per night from Aug 27 to Aug 28
$84 total
Aug 27 - Aug 28
Total with taxes and fees
8/10 Very Good! (646 reviews)
"Right off the expressway. They were very clean and had a nice night!"

Reviewed on Aug 24, 2025

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
$77 nightly
The price is $89 total per night from Aug 28 to Aug 29
$89 total
Aug 28 - Aug 29
Total with taxes and 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 71 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.

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Frequently asked questions

How much does a Diamond vacation package cost?
You'll find cheap prices from $420 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.