Diamond Vacations from $425

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The Latest Diamond vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $757, price is now $425 per person
$425
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
Very nice hotel and very clean , right in the middle of everything , within walking distance to everything . The included bread was very good, with lots of options . The roof top restaurant is amazing , with great views and a great atmosphere.

Reviewed on Sep 9, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,331, price is now $681 per person
$681
per person
Oct 16 - Oct 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,129 reviews)
Please share something about the coffee & breakfast cafe with guests checking in. Many of us were checking out before we noticed it was there.

Reviewed on Sep 7, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $2,059, price is now $1,075 per person
$1,075
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.

Reviewed on Sep 8, 2025

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $1,035, price is now $628 per person
$628
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (237 reviews)
New hotel with a friendly staff and clean modern rooms.

Reviewed on Sep 8, 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,672, price is now $1,042 per person
$1,042
per person
Oct 16 - Oct 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,032 reviews)
It was great for a short stay with my family. We enjoyed the location and proximity to public transportation.

Reviewed on Sep 4, 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
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
$53 nightly
The price is $61 total per night from Sep 11 to Sep 12
$61 total
Sep 11 - Sep 12
Total with taxes and fees
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
$80 nightly
The price is $93 total per night from Sep 10 to Sep 11
$93 total
Sep 10 - Sep 11
Total with taxes and fees
Super 8 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.

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Frequently asked questions

How much does a Diamond vacation package cost?
You'll find cheap prices from $425 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.