Hillcrest Holidays from £445

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Your Hillcrest Holiday

Unforgettable adventures await when you book a holiday package to Hillcrest. Whether you're a foodie, art buff or just a traveller who loves experiencing new places, there's something for everyone in this vibrant city. Every good trip to Hillcrest should include some sightseeing. What to do first? Rochelle Railroad Park and Chicagoland Skydiving Centre are major attractions. Whatever your travel plans or the size of your budget, organising your ultimate tailored Hillcrest holiday is a breeze with Expedia.

Top Hillcrest Flight + Hotel 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
per person
6 Nov - 10 Nov
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location of this hotel is outstanding. A quick four block walk to the train stations, including all the "L" lines. So close to State and Michigan Ave as well. The bed was completely comfortable and the room was well maintained. I am not a coffee drinker, but there is no coffee in the rooms itself, but they serve it complimentary in the lobby area each morning. The bar was great, with a pleasant bartender. I would definitely stay there again.

Reviewed on 17 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on 16 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
This was property was centrally located next to everything that a first time visitor would like to experience. The access to the parks, museums, the Riverwalk and dining options makes for an enjoyable trip. The only downside was having to wait a considerable time for the elevators. Having 5 elevators and not all running at the same time, led to long wait times for a popular hotel with many guests.

Reviewed on 17 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
6 Nov - 10 Nov
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great property. Outstanding all the way around.

Reviewed on 13 Aug 2025

Hillcrest Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
1,300
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Chicagoland Skydiving Centre, Rochelle Railroad Park and Stillmans Defeat Memorial Site

Top hotels in Hillcrest

Country Inn & Suites by Radisson, Sycamore, IL

Country Inn & Suites by Radisson, Sycamore, IL

2.5 out of 5
1450 South Peace Road, Sycamore, IL
Fully refundable
The price is £78 per night from 21 Aug to 22 Aug
£78
21 Aug - 22 Aug
includes taxes & fees
8.6/10 Excellent! (864 reviews)
"The bed was super comfortable. The pillows were amazing."

Reviewed on 10 Aug 2025

Country Inn & Suites by Radisson, Sycamore, IL
Hampton Inn DeKalb, IL

Hampton Inn DeKalb, IL

3 out of 5
663 S. Annie Glidden Road, DeKalb, IL
Fully refundableReserve now, pay when you stay
The price is £103 per night from 31 Aug to 1 Sept
£103
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (943 reviews)
"Everything was clean very comfortable and the staff was decent. The only problem I had was when I’d come home at night. The TV didn’t always work. Had Wi-Fi issues. Breakfast is what you’d expect from premade food. Taste was good."

Reviewed on 15 Aug 2025

Hampton Inn DeKalb, IL
Hotel Weston RFD

Hotel Weston RFD

2.5 out of 5
3909 11th St, Rockford, IL
Fully refundableReserve now, pay when you stay
5.4/10 (142 reviews)
"The employees are very nice they show empathy"

Reviewed on 9 Jul 2025

Get rates
Hotel Weston RFD
See all 61 properties in Hillcrest
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.
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Frequently asked questions

How much does a Hillcrest travel package cost?
Our Hillcrest packages, which start at just £445, are the perfect way to save loads of cash. Select your preferred flights, hotels and rental cars to create a personalized getaway.
If I'm not able to travel, can I cancel my Hillcrest travel package?
It's hard to predict what the future holds, so it's comforting to know that you can cancel or change your Hillcrest travel package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.
How do I get a cheap travel package to Hillcrest?
You'll save a ton of money if you combine your flights, hotels and car rentals into a Hillcrest travel package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties worldwide, so you'll always have plenty of options to choose from. Want to save even more? Add some interesting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Does Expedia offer Book Now, Pay Later Hillcrest holidays?
Yes. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply pick the payment plan best suited to your needs during checkout and take away the stress of budgeting for your next trip. Remember to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that work for all budgets, so you can have that well-earned holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your trip in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan with Klarna.

Where should I stay in Hillcrest?
If you aim to visit Rochelle Railroad Park, forget about commuting and find a place to stay close by. It's one of the most popular attractions in Hillcrest.
What are the top hotels in Hillcrest?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are among the most well-known hotels in Hillcrest. Why not look up the amenities and rates at each and then decide?
How far in advance should I book my Hillcrest holiday?
Reward yourself with the biggest variety at the cheapest prices by booking your holiday to Hillcrest early. Airlines usually publish flight tickets anywhere up to a year before departure, so secure your spot ASAP. That being said, Expedia is dedicated to providing you with the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Hillcrest travel package include?
Hotels, flights and rental cars — you'll discover them all here. With Expedia, you can create your Hillcrest package however you want. All you have to do is work out just what you need. Once you've made your booking, you can add on extras like tours and activities. The more you bundle, the bigger your savings!
What should I know before booking a Hillcrest travel package?
When you book your hotels, flights and car rentals together, you'll pick up amazing discounts. Whether you're organising a beach escape in a villa or would rather stay in a cosy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a Hillcrest Expedia travel package?
Most definitely. Expedia has more than 550 partner airlines to choose from all over the world. With such a huge range of choice, finding the perfect carrier to whisk you away to Hillcrest will be a cinch.

* 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.