Hillside Vacations from ￥372,235
Book a Hotel + Flight or Car together to unlock savings
The Latest Hillside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥454,382
per person
Oct 1 - Oct 8
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
I’ve stayed at several hotels in this area and the Silversmith is by far the nicest. The hotel staff were very friendly and accommodating. The room was clean, comfortable and quiet. Highly recommend!
Reviewed on Aug 31, 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
￥402,942
per person
Oct 1 - Oct 8
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (3,932 reviews)
Hotel look is a bit dated but location is great! Friendly and helpful staff with great views of city
Reviewed on Aug 31, 2026
Find the Best Hillside Vacation Packages
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,900
￥20,092 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (10,237 reviews)
"Room was clean, bathroom was old and a bit smelly. Was fine for the one night we were there - a bit pricey tho"
Reviewed on Aug 31, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥24,329
￥28,924 total
Sep 29 - Sep 30
includes taxes & fees
8/10 Very Good! (2,133 reviews)
"Loved this hotel, great location and wonderful accommodations, just perfect"
Reviewed on Aug 31, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (882 reviews)
"Love the layout. Great location. Super easy check in and check out"
Reviewed on Aug 30, 2026
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.
What to do in Hillside
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
Frequently asked questions
How much does a Hillside vacation package cost?
Offering excellent value package deals from ￥372,235 on Expedia, you'll be thrilled with how little a vacation to Hillside costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Hillside?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Hillside vacation packages and you could get some great off-season discounts.
How many days is enough for Hillside?
Typically, a handful of days is enough to check out the top attractions during your Hillside vacation. But if you'd like to have more time to rest or take day trips, consider extending your itinerary.
How to find the best Hillside package deals?
Landing a cheap Hillside package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Hillside package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Hillside vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Hillside escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Hillside?
If you're considering an impromptu Hillside getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Hillside?
- Choose your travel dates: What you'd like to do in Hillside and your favorite season can help you decide when to travel.
- Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Hillside.
- Decide how long to go away for: Now that you're more familiar with Hillside, you can figure out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Hillside vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
