Hillsdale Vacations from $367

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The Latest Hillsdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $616, price is now $367 per person
$367
per person
Mar 25 - Mar 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was $1,719, price is now $904 per person
$904
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on Jan 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,230, price is now $1,206 per person
$1,206
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing

Reviewed on Jan 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $704, price is now $387 per person
$387
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
everything was awesome. The room was amazing. The staff was very helpful. The entire hotel was very clean. The only drawback was the water pressure in the sink. We had a room with two sinks, and both sinks had low water, pressure and lukewarm water. It never did get hot.

Reviewed on Jan 19, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $664, price is now $373 per person
$373
per person
Mar 25 - Mar 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
no the room was dirty and smell musty

Reviewed on Jan 18, 2026

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Hillsdale Hotel Deals

La Quinta Inn by Wyndham Davenport & Conference Center

La Quinta Inn by Wyndham Davenport & Conference Center

3 out of 5
3330 E Kimberly Rd Davenport IA
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $74 total per night from Jan 25 to Jan 26
$74 total
Jan 25 - Jan 26
Total with taxes and fees
7.2/10 Good! (1,006 reviews)
Comfortable and relaxed

Reviewed on Dec 27, 2025

La Quinta Inn by Wyndham Davenport & Conference Center
DoubleTree by Hilton Davenport

DoubleTree by Hilton Davenport

4 out of 5
111 E 2nd St Davenport IA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $77 total per night from Feb 1 to Feb 2
$77 total
Feb 1 - Feb 2
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
Clean room, extremely friendly staff, and loved that there was a skywalk to our venue!

Reviewed on Jan 12, 2026

DoubleTree by Hilton Davenport
Stoney Creek Hotel Quad Cities - Moline

Stoney Creek Hotel Quad Cities - Moline

2.5 out of 5
101 18th St Moline IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $97 total per night from Jan 27 to Jan 28
$97 total
Jan 27 - Jan 28
Total with taxes and fees
8.2/10 Very Good! (1,099 reviews)
Clean rooms very friendly staff

Reviewed on Jan 12, 2026

Stoney Creek Hotel Quad Cities - Moline
See all 326 properties in Hillsdale
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.

Find the Best Hillsdale Vacation Packages

Hillsdale Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Quad City Intl. Airport (MLI)
Population
510
Top Sights
Cordova Dragway Park and Illiniwek Forest Preserve

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Frequently asked questions

How much does a Hillsdale vacation package cost?
Offering great value package deals from $367 on Expedia, you'll be surprised at how little a vacation to Hillsdale costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Hillsdale?
You can generally find lower prices and better availability in November, December and January. Take a look at our cheap Hillsdale vacation packages and you could score some excellent off-season deals.
How many days is enough for Hillsdale?
Usually, a handful of days is enough to go to the main sights during your Hillsdale vacation. But if you prefer to have time to unwind or take day tours, think about extending your trip.
How to find the best Hillsdale package deals?
Start your search for a Hillsdale package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Hillsdale package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillsdale escape off to a flying start.
Is it cheaper to book a Hillsdale vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still get the freedom to create a personalized Hillsdale vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Hillsdale?
If you have your Hillsdale travel dates finalized, book as early as you can to bag some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Hillsdale vacation packages?
Your Hillsdale break is meant to be a relaxing escape from your busy life, not a source of money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.