Diamond Vacation Packages

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    Save up to CA $1,096 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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Top Diamond Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $747, price is now CA $442 per person
CA $442
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on Aug. 25, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,989, price is now CA $1,147 per person
CA $1,147
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,892, price is now CA $1,124 per person
CA $1,124
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on Aug. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,647, price is now CA $997 per person
CA $997
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,838, price is now CA $1,118 per person
CA $1,118
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Ready to book your vacation to Diamond?

 

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Diamond Hotel Deals

aruba- la cabana beach resort and casino

aruba- la cabana beach resort and casino

Diamond
Get rates
aruba- la cabana beach resort and casino
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 CA $105 per night from Sep 8 to Sep 9
CA $105
CA $122 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (646 reviews)
"Right off the expressway. They were very clean and had a nice night!"

Reviewed on Aug. 24, 2025

Super 8 by Wyndham Joliet
Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

2.5 out of 5
101 McDonald Avenue, Joliet, IL
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Sep 1 to Sep 2
CA $111
CA $129 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
Nice place
"Nice and clean, with exceptional service from front desk staff."

Reviewed on Aug. 22, 2025

Wingate 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Diamond vacation package cost?
You can pick up a vacation package to this popular destination from CA $442 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.