Diamond Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

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

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

Top Flight + Hotel Deals in Diamond

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Doorman was delightful! King room was spacious. Toilet flush was problematic. The pool was not open despite the advertisement on the Expedia websit. Lots of additional, non-negotiable charges once you get there.

Reviewed on 11 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on 11 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on 11 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Beautiful hotel in great location. The food option at hotel are great with good food. It is walkable to surrounding attractions.

Reviewed on 10 Aug 2025

Top hotels in Diamond

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
The price is €54 per night from 18 Aug to 19 Aug
€54
18 Aug - 19 Aug
includes taxes & fees
6.6/10 (1,003 reviews)
"Quiet and clean"

Reviewed on 7 Aug 2025

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
The price is €66 per night from 19 Aug to 20 Aug
€66
19 Aug - 20 Aug
includes taxes & fees
8/10 Very Good! (629 reviews)
"This is a clean and quiet no frills hotel. I chose it for economical rates and convenient location (close to interstates.) I was impressed with the hard-working and graciously courteous management. I’ll stay here again."

Reviewed on 11 Aug 2025

Super 8 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.

Frequently asked questions

How much does a Diamond holiday package cost?
You'll find cheap prices from €727 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.