Hillcrest Holidays from £1,364

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Your Hillcrest Holiday

Our holiday packages to Hillcrest let you create your own adventure. Tailor your journey to suit your interests and needs and make the most of your time in this fabulous city. When it's time to head out and see the sights, be sure to put Chicagoland Skydiving Centre and Rochelle Railroad Park on the itinerary for your trip to Hillcrest. A few clicks is all it takes to build your perfect Hillcrest holiday on Expedia.

The Latest Hillcrest Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
16 Jul - 23 Jul
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
Great location; clean, comfortable room. Love art deco decor

Reviewed on 28 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Jul - 23 Jul
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Extremely neat.and the complimentary suana

Reviewed on 28 May 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Jul - 23 Jul
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.8/10 Exceptional! (1,012 reviews)
Everything was up to higher standard and beyond

Reviewed on 28 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
16 Jul - 23 Jul
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
16 Jul - 23 Jul
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Excellent location! Walk out of the hotel, cross the street and you’re in the middle of all the action. Rooftop bar has spectacular views although no dedicated space for hotel guests. Bed was comfortable, rooms were spacious with nice views. I also liked that you can text your requests to the front desk. They charge $50 an hour for late check out which we utilized.

Reviewed on 29 May 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Jul - 23 Jul
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Stile, breakfast, location

Reviewed on 27 May 2024

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

Super 8 by Wyndham Rochelle
Super 8 by Wyndham Rochelle
2 out of 5
601 E Highway 38, Rochelle, IL
Stay at this motel in Rochelle. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very Good! (728 reviews)
"Decent place for one night"

Reviewed on 20 May 2024

Super 8 by Wyndham Rochelle
Hampton Inn DeKalb, IL
Hampton Inn DeKalb, IL
3 out of 5
663 S. Annie Glidden Road, DeKalb, IL
Stay at this 3-star hotel in DeKalb. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.4/10 Exceptional! (689 reviews)
"Clean, quiet, and easy check in."

Reviewed on 25 May 2024

Hampton Inn DeKalb, IL
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
1133 N 7th St, Rochelle, IL
Stay at this business-friendly hotel in Rochelle. Enjoy free breakfast, free parking and a 24-hour front desk. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (308 reviews)
"Everything was great"

Reviewed on 20 May 2024

Comfort Inn & Suites
See all 54 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 £1,364, 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.