Hillcrest Vacations from $501

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 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

Your Hillcrest Vacation

Unforgettable adventures await when you book a vacation package to Hillcrest. Whether you're a foodie, art buff or just a traveler 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 Center are major attractions. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Hillcrest vacation is a breeze with Expedia.

The Latest Hillcrest vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $947, price is now $501 per person
$501
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Absolutely lovely and helpfully staff

Reviewed on Oct 8, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,358, price is now $1,275 per person
$1,275
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,114, price is now $607 per person
$607
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on Oct 7, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $717 per person
$717
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Perfect location and atmosphere

Reviewed on Oct 7, 2025

Don't see what you're looking for?
See all available trips from Columbus to Hillcrest
View all trips

Hillcrest Hotel Deals

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
$111 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (977 reviews)
"Clean, friendly"

Reviewed on Oct 6, 2025

Hampton Inn DeKalb, IL
Best Western Sycamore Inn

Best Western Sycamore Inn

2.5 out of 5
1935 Dekalb Ave, Sycamore, IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $97 total per night from Oct 16 to Oct 17
$97 total
Oct 16 - Oct 17
Total with taxes and fees
8/10 Very Good! (356 reviews)
"Friendly staff, excellent housekeeping team ."

Reviewed on Aug 20, 2025

Best Western Sycamore Inn
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
$86 nightly
The price is $95 total per night from Oct 13 to Oct 14
$95 total
Oct 13 - Oct 14
Total with taxes and fees
8.4/10 Very Good! (898 reviews)
Wonderful!!!
"The room/ suite was a wonderful surprise, large and clean. The breakfast offered a large variety of options. The staff was very professional, kind and courteous!"

Reviewed on Sep 29, 2025

Country Inn & Suites by Radisson, Sycamore, IL
See all 63 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.

Hillcrest Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
1,300
Top Sights
Chicagoland Skydiving Center, Rochelle Railroad Park and Stillmans Defeat Memorial Site

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Hillcrest vacation package cost?
Offering great value package deals from $501 on Expedia, you'll be pleasantly surprised at how much a vacation to Hillcrest costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Hillcrest?
You can usually find lower prices and better availability in January, March and December. Check out our cheap Hillcrest vacation packages and you could score some excellent off-season deals.
How many days is enough for Hillcrest?
With a well-planned itinerary, you can easily visit the main Hillcrest sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Hillcrest vacation for longer.
How to find the best Hillcrest package deals?
Begin your search for a Hillcrest package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Hillcrest package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Hillcrest getaway off to a flying start.
Is it cheaper to book a Hillcrest vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Hillcrest vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Hillcrest?
If you've got your Hillcrest vacation dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Hillcrest vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Hillcrest trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.