Hillsdale Vacations from ￥89,698

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The Latest Hillsdale Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥113,774, price is now ￥89,698 per person
￥89,698
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
8.4/10 Very Good! (2,079 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥168,504, price is now ￥116,174 per person
￥116,174
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥179,800, price is now ￥138,332 per person
￥138,332
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9.6/10 Exceptional! (1,945 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥128,225, price is now ￥100,296 per person
￥100,296
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on Jul 30, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥111,668, price is now ￥90,778 per person
￥90,778
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
9/10 Wonderful! (3,732 reviews)
Great location, clean and beautiful. Elevator from ground to level floor was out several nights and the rooftop was not open.

Reviewed on Aug 1, 2026

Find the Best Hillsdale Vacation Packages

Hillsdale Hotel Deals

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
The price is ￥16,590 per night from Aug 30 to Aug 31
￥16,590
￥18,743 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (1,260 reviews)
"We were very satisfied with every aspect of this hotel. The room, property, amenities, breakfast, and staff exceeding our expectations. We wouldn’t consider staying anywhere else if we are ever in the area again."

Reviewed on Aug 2, 2026

Wyndham Moline on John Deere Commons
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
The price is ￥14,770 per night from Aug 9 to Aug 10
￥14,770
￥16,542 total
Aug 9 - Aug 10
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"It was very clean and well taken care of."

Reviewed on Aug 2, 2026

DoubleTree by Hilton Davenport
Isle Casino Hotel Bettendorf - A Caesars Rewards Destination

Isle Casino Hotel Bettendorf - A Caesars Rewards Destination

3 out of 5
1777 Isle Pkwy Bettendorf IA
Fully refundableReserve now, pay when you stay
The price is ￥12,608 per night from Aug 16 to Aug 17
￥12,608
￥16,411 total
Aug 16 - Aug 17
includes taxes & fees
Isle Casino Hotel Bettendorf - A Caesars Rewards Destination
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.

Frequently asked questions

How much does a Hillsdale vacation package cost?
Offering great value package deals from ￥89,698 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 typically find lower rates and greater availability in January, February and November. Take a look at our cheap Hillsdale vacation packages and you could land some excellent off-season deals.
How many days is enough for Hillsdale?
With a well-planned itinerary, you can easily tick off the most popular Hillsdale attractions in a handful of days. But if you'd like to venture off the beaten track or go on day trips, consider booking your Hillsdale vacation for longer.
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.
How to plan a trip to Hillsdale?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favorite season and the available activities will also help you decide when to visit Hillsdale.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Hillsdale.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Hillsdale. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, book the right Hillsdale vacation package for you.

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