Diamond Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
€430
per person
7 Jan - 10 Jan
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,727 reviews)
I wouldn’t go back, not even for free.
NO VOLVERIA NI GRATIS
Air conditioning/heating noisy impossible to sleep with it on.
Low shower water pressure, a 5-minute bath becomes 20.
Gym without weight equipment, it only had dumbbells and a bench.
They do not replenish the coffee capsules daily, in 5 days of stay they only did it once
They only have cardboard cups, they don't replace them daily either
On the last day they didn't clean the room (no, I didn't leave the do not disturb sign outside, see cameras). I asked reception to send us towels, because they hadn't changed them, they didn't.
Aire acondicionado/ calefacción ruidosa imposible dormir con ella encendida.
Baja presión del agua de la ducha, un baño de 5 minutos se convierte en 20.
Gimnasio sin equipo para pesas , solo tenía mancuernas y una banqueta.
No reponen diariamente las cápsulas de café, en 5 días de estadía solo lo hicieron una vez
Solo tienen vasos cartón, tampoco los reponen diariamente
El último día no limpiaron la habitación ( no, no dejé el cartel de no perturbar en la parte de afuera, ver cámaras) . Pedí a recepción nos envíen toallas, pues no las habían cambiado, no lo hicieron .
NO VOLVERIA NI GRATIS
Reviewed on 24 Oct 2026
citizenM Chicago Downtown
Downtown Chicago
€398
per person
7 Jan - 10 Jan
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,365 reviews)
Room smelled bad of humidity. Cockroaches in thenroom. Very small rooms. They do not clean the rooms unless you specifically ask, and then even. Comparable to a 50$ motel, yet they charge 500$ a night.
Reviewed on 24 Oct 2026
Top hotels in Diamond
Red Roof Inn Chicago - Joliet
1750 Mcdonough St Joliet IL
Fully refundableReserve now, pay when you stay
€57
8 Nov - 9 Nov
includes taxes & fees
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
151 N Joliet St Joliet IL
€97
22 Nov - 23 Nov
includes taxes & fees
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
€86
22 Nov - 23 Nov
includes taxes & fees
8.4/10 Very good! (1,077 reviews)
"Easy check in and the staff was extremely helpful and friendly for the entire stay."
Reviewed on 23 Oct 2026
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 €338 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?
- 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.
- 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.
- 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.
- 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.
