Diamond Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Diamond

Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

3 out of 5
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is S$131 per night from 20 Jul to 21 Jul
S$131
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"Room & service were good. Breakfast not great. We ate out instead. Would still stay again."

Reviewed on 7 Jul, 2026

Wingate by Wyndham - Joliet
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 S$85 per night from 21 Jul to 22 Jul
S$85
21 Jul - 22 Jul
includes taxes & fees
6.8/10 (1,005 reviews)
"Was put in a handy capped room even though we didn’t book for one. We managed but the smell was bad. Check in should be a little earlier than 3pm not going to lie. Also parking was bad, had to park on the other side of the building due to how many spots were taken. Wouldn’t go back here again"

Reviewed on 7 Jul, 2026

Red Roof Inn Chicago - Joliet
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

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

3.5 out of 5
151 N Joliet St Joliet IL
The price is S$118 per night from 6 Aug to 7 Aug
S$118
6 Aug - 7 Aug
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Rooms were clean"

Reviewed on 6 Jul, 2026

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
See all 77 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.

Frequently asked questions

How much does a Diamond holiday package cost?
You'll find cheap prices 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.