Diamond Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • 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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,049, price is now CA $760 per person
CA $760
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
Very nice rooms. Smaller casino but nice. No late night food options.

Reviewed on Jul 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,258, price is now CA $1,575 per person
CA $1,575
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
There were stains on the carpet and where the thermostat was an awful smell coming from that area-like musty smelling. We stayed and paid premium rate for a firework view and while I know they can’t control the weather, I reached out to see if they would be willing to credit something toward a future stay so we could enjoy the experience. Not even an acknowledgment of our disappointment or receipt of our email. Disappointed in the whole situation.

Reviewed on Jul 10, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,824, price is now CA $1,274 per person
CA $1,274
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on Jul 10, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on Jul 8, 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $2,073, price is now CA $1,493 per person
CA $1,493
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Loved the size of our room and how clean it was.

Reviewed on Jul 9, 2026

Ready to book your vacation to Diamond?

 

Choose your dates

Diamond Hotel Deals

Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

3 out of 5
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Jul 26 to Jul 27
CA $123
CA $142 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very good! (1,011 reviews)
"Really disappointed. The fan in the bathroom was so loud and couldn’t be turned off without turning the lights off. Air conditioning was also very loud that I couldn’t get a good sleep. So if you are sensitive to noise you should avoid it. The room and furniture dated and didn’t feel comfortable ..."

Reviewed on Jul 9, 2026

Wingate by Wyndham - Joliet
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 $75 per night from Jul 13 to Jul 14
CA $75
CA $87 total
Jul 13 - Jul 14
includes taxes & fees
6.8/10 (1,006 reviews)
"Probably wouldn't stay there again. Room had a weird smell to it. Not sure what it was but my suitcase smelled just like it when I got home. Didn't have a good feeling when we first drove up."

Reviewed on Jul 8, 2026

Red Roof Inn Chicago - Joliet
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
151 N Joliet St Joliet IL
The price is CA $91 per night from Aug 9 to Aug 10
CA $91
CA $130 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Very nice rooms. Smaller casino but nice. No late night food options."

Reviewed on Jul 9, 2026

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
See all 76 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 $760 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.