Hillcrest Vacations from $305

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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.
Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,009 reviews)
Bed was comfortable. Room was clean. All staff I came across were friendly, cheerful and polite. Low couch chairs in breakfast area need replacing due to worn out springs. Too low and no longer fit with eating at tables.

Reviewed on Aug 13, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug 12, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on Aug 11, 2025

Hilton Garden Inn Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
quiet, stily , good price

Reviewed on Jul 30, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (431 reviews)
This is my go to place in the south suburbs.

Reviewed on Jul 30, 2025

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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
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $95 total per night from Aug 21 to Aug 22
$95 total
Aug 21 - Aug 22
Total includes taxes and fees
8.6/10 Excellent! (862 reviews)
"The bed was super comfortable. The pillows were amazing."

Reviewed on Aug 10, 2025

Country Inn & Suites by Radisson, Sycamore, 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
$91 nightly
The price is $101 total per night from Aug 31 to Sep 1
$101 total
Aug 31 - Sep 1
Total includes taxes and fees
8/10 Very Good! (347 reviews)
Great location
"Quiet and clean. Great location."

Reviewed on Aug 7, 2025

Best Western Sycamore Inn
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
$127 nightly
The price is $144 total per night from Aug 24 to Aug 25
$144 total
Aug 24 - Aug 25
Total includes taxes and fees
9.2/10 Wonderful! (941 reviews)
"Clean place with a good breakfast. The location was convenient to the downtown and University."

Reviewed on Aug 8, 2025

Hampton Inn DeKalb, IL
See all 60 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 vacation package cost?
Offering great value package deals from $305 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.