Hillside Vacations from $312
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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.
What to do in Hillside
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 22 to Nov 23
$127 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,178 reviews)
"The booking said air conditioning available but there isn’t any. The staff said all they can do is send a fan upstairs."
Reviewed on Nov 11, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 15 to Nov 16
$138 total
Nov 15 - Nov 16
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
$101 nightly
The price is $120 total per night from Nov 23 to Nov 24
$120 total
Nov 23 - Nov 24
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
