Hillside Vacations from $487
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Your Hillside Vacation
An easy way to experience this vibrant city is with a custom-made Hillside vacation package. Base yourself in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our packages are all about you. Any trip to Hillside needs a well-planned itinerary. Fill yours with major attractions such as Brookfield Zoo, Oakbrook Center Mall and Yorktown Shopping Center. Expedia can help you escape the everyday. Tailor your vacation to Hillside to suit your style of travel, whatever that may be.
The Latest Hillside vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$638
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Absolutely perfect location and friendly and accommodating staff. The room was wonderful; comfortable, especially the bathroom. We really enjoyed having the double sinks, and the showerhead was luxurious. Fabulous breakfast, and the staff handled the comings and goings of the many guests effortlessly. The Halloween paraphernalia was a little over the top and unnecessary, in my opinion.
Reviewed on Oct 9, 2026
What to do in Hillside
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$123 nightly
$146 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (10,141 reviews)
"The first"
Reviewed on Oct 9, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundable
$152 nightly
$181 total
Oct 25 - Oct 26
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
$170 total
Nov 1 - Nov 2
Total with taxes and fees
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 Hillside Vacation Packages
Hillside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 8,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District |
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Frequently asked questions
How much does a Hillside vacation package cost?
Offering excellent value package deals from $487 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?
November, December and January are the best times to search for cheap Hillside vacation packages. Choosing to travel in quieter periods means you can generally find reduced prices on flights and hotels.
How many days is enough for Hillside?
The ideal duration for your Hillside vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to go to all the top attractions and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Hillside vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Hillside vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
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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.
