Diamond Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Diamond Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel 505 River North
Downtown Chicago
CA $1,216
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,924 reviews)
The property is in a great location. The rooms are ok nothing special. Needs better attention to cleanliness; I found hair in the bathroom. The restaurant is very poor; the menu is below average, and the buffet breakfast is worse than a free Holiday Inn breakfast, yet they still wanted to charge you $40 for it. If you arrive late, after 10 pm, you can not find food on the premises, not even room service. No restaurant on Sundays and Mondays. I would say the only good thing was location.
Reviewed on Oct 13, 2026
Ready to book your vacation to Diamond?
Diamond Hotel Deals
Red Roof Inn Chicago - Joliet
1750 Mcdonough St Joliet IL
Fully refundableReserve now, pay when you stay
CA $76
CA $88 total
Oct 14 - Oct 15
includes taxes & fees
6.8/10 (1,006 reviews)
"Floor so filthy had to spread towels on the floor to walk around. No elevator, no coffee, no juice, no breakfast. Bathtub filthy. There was a safe in the room but anyone with anything of value would NEVER stay here."
Reviewed on Oct 11, 2026
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
151 N Joliet St Joliet IL
CA $112
CA $155 total
Nov 11 - Nov 12
includes taxes & fees
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
CA $130
CA $150 total
Nov 1 - Nov 2
includes taxes & fees
8.4/10 Very good! (1,067 reviews)
"Our bathroom door was broken, no lock on the bathroom door, no hooks or towel bars. The tile in the shower , I recommend shower shoes. It’s old, I have seen cleaner campgrounds. The rooms are small, no pull out couches for a family of four. The staff was nice, however for the amount of money we paid, ..."
Reviewed on Oct 11, 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 vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,216 on Expedia. But how much your vacation to Diamond costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Diamond?
If you're hoping to book a cheap Diamond vacation package, consider planning a trip in January, February and March. You'll usually find better rates on airfares and hotels during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Diamond?
With a well-planned itinerary, you can easily hit the most popular Diamond sights in a few days. But if you prefer to explore off the beaten track or take day trips, think about booking your Diamond vacation for longer.
How to find the best Diamond package deals?
Landing a cheap Diamond package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Diamond package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Diamond vacation as a package?
You can enjoy significant savings on your next Diamond retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Diamond?
Score fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Diamond adventure.
How to plan a trip to Diamond?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Diamond.
- Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will probably be the largest expense during your trip to Diamond.
- Decide your trip length: Consider how much time you'd like to spend exploring Diamond. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Diamond vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
