Diamond Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Top Diamond Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,405 reviews)
We try to stay here every time we come to Chicago.

Reviewed on Aug. 3, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
I booked a room with the water view, when I checked in I asked before I get the key, Is it a water view. They told me it is. I show up in my room and it’s not the room I booked. I called the front desk and they’re telling me we apologize all of the rooms are booked with the water view. They also said booking a water view room doesn’t guarantee a water view room even though I paid extra for a water view room! Never going to stay there again for sure.

Reviewed on Aug. 3, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on Aug. 3, 2025

Ready to book your vacation to Diamond?

 

Choose your dates

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
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 CA $67 per night from Aug 10 to Aug 11
CA $67
CA $78 total
Aug 10 - Aug 11
includes taxes & fees
6.6/10 (1,001 reviews)
"I love the cleanliness of the room"

Reviewed on Jul. 29, 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 CA $97 per night from Aug 17 to Aug 18
CA $97
CA $112 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (619 reviews)
"We stayed for two nights. When we checked in, we asked for a hairdryer, but were told they didn’t provide one. However, when we came back on the second day, the room had been cleaned and a hairdryer was kindly placed under the sink. Very thoughtful and much appreciated."

Reviewed on Jul. 29, 2025

Super 8 by Wyndham Joliet
See all 70 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 $862 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.