Diamond Vacations from $328

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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
Price was $594, price is now $328 per person
$328
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.

Reviewed on Jan 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,000, price is now $485 per person
$485
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.

Reviewed on Jan 20, 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $903, price is now $492 per person
$492
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Room was extremely clean, and staff was very accommodating

Reviewed on Jan 17, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,017, price is now $564 per person
$564
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on Jan 8, 2026

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $666, price is now $392 per person
$392
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,059 reviews)
Besides the ambience and location of this gorgeous hotel... we enjoyed winding down the evening with a drink and Bertha's brownie in the lobby/lounge.

Reviewed on Jan 18, 2026

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Diamond Hotel Deals

aruba- la cabana beach resort and casino

aruba- la cabana beach resort and casino

Diamond IL
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
$51 nightly
The price is $59 total per night from Jan 22 to Jan 23
$59 total
Jan 22 - Jan 23
Total with taxes and fees
6.6/10 (1,004 reviews)
Nice room!!

Reviewed on Jan 15, 2026

Red Roof Inn Chicago - 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
$81 nightly
The price is $94 total per night from Jan 27 to Jan 28
$94 total
Jan 27 - Jan 28
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
The staff was nice, the room was clean, the bed was very comfortable, lots of good food options. The pool was temporarily unavailable, but that didn't matter to us.

Reviewed on Jan 18, 2026

Wingate by Wyndham - Joliet
See all 81 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 $328 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.