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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,110, price is now CA $797 per person
CA $797
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
First time ever in Chicago and it was fabulous. The hotel was beautiful. Staff was friendly. We paid for the view and it was phenomenal. Definitely recommend.

Reviewed on Nov 12, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,079, price is now CA $1,318 per person
CA $1,318
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Great location. Rooms are spacious and staff is amazing!! I would highly recommend!!!

Reviewed on Nov 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,806, price is now CA $1,260 per person
CA $1,260
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $1,944, price is now CA $1,379 per person
CA $1,379
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,256, price is now CA $2,339 per person
CA $2,339
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 2026

Ready to book your vacation to Diamond?

 

Choose your dates

Diamond Hotel Deals

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 Dec 1 to Dec 2
CA $75
CA $87 total
Dec 1 - Dec 2
includes taxes & fees
Red Roof Inn Chicago - Joliet
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

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

3.5 out of 5
151 N Joliet St Joliet IL
The price is CA $111 per night from Dec 13 to Dec 14
CA $111
CA $154 total
Dec 13 - Dec 14
includes taxes & fees
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
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 $116 per night from Nov 25 to Nov 26
CA $116
CA $135 total
Nov 25 - Nov 26
includes taxes & fees
Super 8 by Wyndham Joliet
See all 66 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 $797 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.