Hillsdale Vacations from $591

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The Latest Hillsdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,096, price is now $591 per person
$591
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Staff was friendly and helpful. Great value for price we paid.

Reviewed on Jul 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,507, price is now $790 per person
$790
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Great place and location.

Reviewed on Jul 15, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,446, price is now $811 per person
$811
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Holes in the carpeting in living room. Door that enters unit doesn’t close without slamming it. Looks like wear and tear since we were there before.

Reviewed on Jul 14, 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $1,044, price is now $599 per person
$599
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I enjoyed my stay here. Clean room, well maintained property and great location just 3 miles from Chicago. The best part was the friendly staff. The breakfast was a 4.5 out 5, just adequate foe the day's need, nothing super special. I would definitely return.

Reviewed on Jul 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,717, price is now $991 per person
$991
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Free beer no perfect everyone was great

Reviewed on Jul 15, 2026

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Hillsdale Hotel Deals

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
$84 nightly
The price is $94 total per night from Jul 19 to Jul 20
$94 total
Jul 19 - Jul 20
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"Very friendly, efficient staff - Nathan was particularly fun. Room was clean, and breakfast had a wide variety of choices and quite delicious. Wish the second elevator was working, but we didn't have to wait too long for the one that was - just a bit crowded around check-out. We've stayed here twice, ..."

Reviewed on Jul 14, 2026

DoubleTree by Hilton Davenport
Wyndham Moline on John Deere Commons

Wyndham Moline on John Deere Commons

3.5 out of 5
1415 River Dr Moline IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Jul 19 to Jul 20
$114 total
Jul 19 - Jul 20
Total with taxes and fees
9/10 Wonderful! (1,256 reviews)
"great experience worth the monet"

Reviewed on Jul 13, 2026

Wyndham Moline on John Deere Commons
Isle Casino Hotel - Bettendorf

Isle Casino Hotel - Bettendorf

3 out of 5
1777 Isle Pkwy Bettendorf IA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $114 total per night from Jul 16 to Jul 17
$114 total
Jul 16 - Jul 17
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"The staff up front was very helpful! The parking was convenient"

Reviewed on Jul 14, 2026

Isle Casino Hotel - Bettendorf
See all 348 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 $591 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.