Hillcrest Holidays from £876

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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.

The Latest Hillcrest Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago

4 out of 5
per person
18 Sept - 23 Sept
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Parking lot under construction messing amd challenging to get to main entrance. Front desk staff pleasant and very helpful. Inner building lacked clear instruction to locate pool, sauna steam room. Rooms were excellent bed super comfy. Disappointed in breakfast i miss understood i thought set up was brunch. Overall ok nearby Oak Brook mall and fine eatry. Review other spa like lodges before locking into this location. Happy travels....

Reviewed on 3 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Staff was very friendly and helpful. We had a great stay in every way possible!

Reviewed on 30 Jun 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair.

Reviewed on 1 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Always love our stay at The Peninsula!

Reviewed on 29 Jun 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
I had such a lovely staycation, and I recommend a stay here to everyone I know.

Reviewed on 26 Jun 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,549 reviews)
The staff was so kind. The room was amazing. Our new go-to for Chicago.

Reviewed on 2 Jul 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

Our pick of the best Hillcrest Hotel Deals

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
Stay at this business-friendly hotel in Sycamore. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (828 reviews)
Nice.
"Enjoyed the stay. Elevator was out so booked me to the 2nd floor. Enjoyed."

Reviewed on 30 Jun 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
Stay at this 3-star business-friendly hotel in DeKalb. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (917 reviews)
"Professional and friendly staff. Cleanliness of hotel"

Reviewed on 30 Jun 2025

Hampton Inn DeKalb, IL
Best Western Sycamore Inn
Best Western Sycamore Inn
2.5 out of 5
1935 Dekalb Ave, Sycamore, IL
Stay at this business-friendly hotel in Sycamore. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the clean rooms in their reviews. Popular ...
8/10 Very Good! (329 reviews)
"The shower is nice and housekeeping came most days. However the breakfast is awful. Packets of oatmeal, now a yogurt machine. Hot water dispenser never properly cooks the oatmeal. For these they provide "mix ins" which included dried apples amd brown sugar. That's it. The hot opetions always involve ..."

Reviewed on 28 Jun 2025

Best Western Sycamore Inn
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Hillcrest travel package cost?
Our Hillcrest packages, which start at just £876, 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.