Hillside Vacations from $208
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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.
Grand Royal Hotel O'Hare - Chicago
Save 100% on your flight
Price was $315, price is now $208 per person
$208
per person
Feb 28 - Mar 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago
Reviewed on Nov 7, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $667, price is now $373 per person
$373
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Superb customer service and staff, clean room and common areas, and awesome breakfast buffet.
Reviewed on Jan 27, 2026
La Banque Hotel
Save 100% on your flight
Price was $616, price is now $366 per person
$366
per person
Mar 13 - Mar 16
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $658, price is now $412 per person
$412
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Staff was kind and it was at a great location!
Reviewed on Jan 27, 2026
Springhill Suites by Marriott Chicago Downtown/ River North
Downtown Chicago
Save 100% on your flight
Price was $542, price is now $357 per person
$357
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
We really liked the comfort of the bed, the pillows, the view, and the hotel was very clean. The shower worked really well, and we enjoyed our stay. It was very pleasant, and the staff was great.
Reviewed on Jan 26, 2026
Discover the most popular places to visit in Hillside
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Hillside
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $104 total per night from Jan 31 to Feb 1
$104 total
Jan 31 - Feb 1
Total with taxes and fees
8/10 Very Good! (9,832 reviews)
Yes perfectly clean
Reviewed on Jan 24, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Feb 5 to Feb 6
$124 total
Feb 5 - Feb 6
Total with taxes and fees
8.4/10 Very Good! (5,616 reviews)
The room was clean. The staff was courteous! The breakfast was ok, the parking is charged extra-absolutely worth it!
Reviewed on Jan 26, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Feb 3 to Feb 4
$100 total
Feb 3 - Feb 4
Total with taxes and fees
8.6/10 Excellent! (2,265 reviews)
Great
Reviewed on Jan 27, 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 |
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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.
