Hillside Vacations from $715
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
$876
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The staff, breakfast, and location was excellent. The only negative there was no ice machine or microwave available. We had to go to the bar for ice which was inconvenient.
Reviewed on Aug 25, 2026
What to do in Hillside
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$113 nightly
$135 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (10,313 reviews)
"Great location, serious service and sanitation failures. Rooms are dated, which could be charming. The TV has basic channels only, so bring a Chromecast or Roku. The in room tablet is useless; that money should have gone to the TVs. Room service never came. I ordered biscuits and gravy and pancakes. ..."
Reviewed on Aug 25, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
$159 total
Aug 31 - Sep 1
Total with taxes and fees
8/10 Very Good! (2,096 reviews)
"The international breakfast was amazing. The valet was prompt."
Reviewed on Aug 25, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$256 nightly
$300 total
Sep 18 - Sep 19
Total with taxes and fees
8.4/10 Very Good! (2,442 reviews)
"It is located walking distance within the airport"
Reviewed on Aug 25, 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.
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 |
More vacations you might like
Frequently asked questions
How much does a Hillside vacation package cost?
Offering excellent value package deals from $715 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
- Flat Iron Building
- West Loop Vacations
- Packer Schopf Gallery
- Westchester Vacations
- Lakeview Vacations
- University of Illinois Chicago
- Broadview Vacations
- Apollo Theater Chicago
- 333 West Wacker Drive
- Richard J. Daley Center
- Montrose Beach
- Ping Tom Memorial Park
- Magnificent Mile Vacations
- Tribune Tower
- Humboldt Park
- Gorilla Tango Theatre
- Rainbow Falls Waterpark
- House of Blues Chicago
- Chicago Cultural Center
- Oak Brook Golf Course
- Illinois Centennial Memorial Column
- Cibc Theatre
- Cantigny Park
- Armitage Avenue
- The East Bank Club
- Navy Pier
- Shops at North Bridge
- Chicago Vacations
- Chase Tower
- Holy Trinity Russian Orthodox Cathedral
- Jane Addams' Hull-House Museum
- Baha'i House of Worship
- Skydeck Ledge
- Ohio Street Beach
- Picasso Statue
- Mary Bartelme Park
- Merchandise Mart
- Vic Theatre
- Anna and Frederick Douglass Park
- Elmhurst Vacations
- Depaul University-Lincoln Park
- Wicker Park Vacations
- Our Lady of Sorrows Basilica
- Garfield Park
- Cadillac Palace Theatre
- Lincoln Park Conservatory
- Rookery
- Marina City
- Wrigley Building
- Legoland® Discovery Center
- Cooking & Hospitality Institute of Chicago
- St Nicholas Ukrainian Catholic Cathedral
- American Police Center & Museum
- St. Josaphat Church
- Driehaus Museum
- Roosevelt University
- Michigan Avenue
- Bellwood Vacations
- Carbide and Carbon Building
- Civic Opera House
- North Avenue Beach
- Raging Waves Waterpark
- Woodfield Mall
- International Museum of Surgical Science
- Canalport Riverwalk Park
- Oakbrook Center Mall
- Lincoln Park Zoo
- Goose Island Vacations
- Garfield Park Conservatory
- Centennial Beach
- Depaul Art Museum
- The Salt Shed
- Monique Meloche Gallery
- St. John Cantius Church
- Advocate Illinois Masonic Medical Center
- Wrigley Field
- Depaul University-Loop Campus
- Morton Arboretum
- 311 S Wacker Dr
- Robie House
- Chicago City Hall
- Wrigley View Rooftop
- Art Institute of Chicago
- Willis Tower
- Bridgeport Art Center
- Chicago Place Mall
- Grace Abbott Homes Vacations
- Marshall Field Building
- Defiant Theatre
- St. Basil Greek Orthodox Church
- York Woods County Forest Preserve
- Holy Name Cathedral
- Maxwell Street Market
- Briar Street Theatre
- 900 North Michigan Shops
- Fourth Presbyterian Church
- Chicago Children's Museum
- Unity Temple
- Goodman Theater
- Zhou B Art Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
