Diamond Holidays from £1,107

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Top Diamond Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,491, price is now £1,107 per person
£1,107
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
Everything was great

Reviewed on 8 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,851, price is now £1,969 per person
£1,969
per person
12 Sept - 19 Sept
found 14 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on 6 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,231, price is now £1,589 per person
£1,589
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
Big five star

Reviewed on 7 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,696, price is now £1,242 per person
£1,242
per person
30 Sept - 5 Oct
found 21 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £1,831, price is now £1,382 per person
£1,382
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
Great stay , great location

Reviewed on 6 Jul 2026

Diamond Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Heidecke Lake State Fish and Wildlife Area, Gebhard Woods State Park and William G. Stratton State Park

Top hotels in Diamond

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 £75 per night from 19 Jul to 20 Jul
£75
19 Jul - 20 Jul
includes taxes & fees
8.4/10 Very good! (1,009 reviews)
"The breakfast was quite good. I found good dairy free options for tea. I am gluten intolerant and brought my own bread. We used the pool and hot tub and it was so welcoming. This motel by Wyndham was a big step up from the Days Inn."

Reviewed on 8 Jul 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 £49 per night from 26 Jul to 27 Jul
£49
26 Jul - 27 Jul
includes taxes & fees
6.8/10 (1,005 reviews)
"Was put in a handy capped room even though we didn’t book for one. We managed but the smell was bad. Check in should be a little earlier than 3pm not going to lie. Also parking was bad, had to park on the other side of the building due to how many spots were taken. Wouldn’t go back here again"

Reviewed on 7 Jul 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 £82 per night from 9 Jul to 10 Jul
£82
9 Jul - 10 Jul
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Rooms were clean"

Reviewed on 6 Jul 2026

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
See all 77 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Diamond travel package cost?
From just £1,107. Yes, you read that correctly. Our Diamond travel packages are a simple way to make your budget stretch further. Combine your hotels, flights and car rentals and get out and explore this popular destination.
If I'm not able to travel, can I cancel my Diamond travel package?
If your travel plans in Diamond have changed, it's good to know that you can amend or cancel your booking. If your booking was made in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Diamond?
Our Diamond holiday packages offer plenty of savings for the savvy globetrotter. For the best deals, simply bundle your flights, hotels and extras (including activities) into a budget-friendly package. But cheap prices are only the start of your next big adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 properties all over the world to pick from. No matter your budget or style, there's a holiday package here just for you.
Does Expedia offer Book Now, Pay Later Diamond holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply click on the payment plan that suits you best during checkout and take the stress out of budgeting for your trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna.

What are the top hotels in Diamond?
Hampton Inn & Suites Minooka and Comfort Inn Morris I-80 are among the most well-known properties in Diamond. Why not take a look at the facilities and amenities at each and then make up your mind?
How far in advance should I book my Diamond holiday?
Reserving your tickets early with Expedia means one less thing to worry about. Most air carriers display prices up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, discount flights to Diamond sometimes become available just a few weeks before departure.
What does an Expedia Diamond travel package include?
That depends entirely on you. You can select from a range of Diamond bundles, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your Diamond break looks like, you're sure to save!
What should I know before booking a Diamond travel package?
Whether it's adventure or relaxation you're craving, a Diamond travel package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Diamond Expedia travel package?
Yes, and with over 550 airlines to choose from globally, you've got lots of choice. Look through the available options and find out which airline fits your needs and budget.

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. Flight-inclusive packages are ATOL protected.