Diamond Holidays from AU$3,688

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  • Plan, book, travel with confidence

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    Save up to AU$2,500 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Diamond Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,440, price is now AU$3,688 per person
AU$3,688
per person
28 Dec - 3 Jan
found 5 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,580 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was AU$7,537, price is now AU$5,906 per person
AU$5,906
per person
28 Dec - 3 Jan
found 5 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,711, price is now AU$3,889 per person
AU$3,889
per person
28 Dec - 3 Jan
found 5 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$4,555, price is now AU$3,773 per person
AU$3,773
per person
28 Dec - 3 Jan
found 5 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)
Great.

Reviewed on 10 Nov 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was AU$4,446, price is now AU$3,695 per person
AU$3,695
per person
28 Dec - 3 Jan
found 5 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Diamond Holiday

Diamond Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
William G. Stratton State Park, Heidecke Lake State Fish and Wildlife Area and Gebhard Woods State Park

Our pick of the best Diamond Hotel Deals

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
The price is AU$90 per night from 1 Dec to 2 Dec
AU$90
1 Dec - 2 Dec
includes taxes & fees
Red Roof Inn Chicago - Joliet
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
151 N Joliet St Joliet IL
The price is AU$158 per night from 10 Dec to 11 Dec
AU$158
10 Dec - 11 Dec
includes taxes & fees
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
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
The price is AU$138 per night from 25 Nov to 26 Nov
AU$138
25 Nov - 26 Nov
includes taxes & fees
Super 8 by Wyndham Joliet
See all 66 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Diamond holiday package cost?
You'll find cheap prices from AU$3,688 on Expedia for your Diamond escape. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Diamond costs.
What are the cheapest months to go to Diamond?
If you're looking to snag a cheap Diamond holiday package, consider visiting in January, February and March. You'll usually find better prices on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Diamond?
With a well-organised travel plan, you can easily hit the main Diamond sights in a few days. But if you prefer to discover hidden spots or take day trips, consider booking your Diamond holiday for longer.
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 holiday as a package?
You can enjoy significant savings on your next Diamond escape by booking a tailored holiday 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 holiday package to Diamond?
If you're considering an impromptu Diamond holiday, 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.
How to plan a trip to Diamond?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to visit Diamond.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and flights. Your accommodation will likely be the biggest expense during your trip to Diamond.
  3. Decide how long to go for: Now that you know more about Diamond, you can figure out the perfect length of your break. Create a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalised Diamond holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.