Hillside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Joe Farmer
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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.
Top Hillside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,496, price is now CA $958 per person
CA $958
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back
Reviewed on Apr 1, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,735, price is now CA $1,305 per person
CA $1,305
per person
Jun 3 - Jun 6
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing
Reviewed on Mar 27, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,323, price is now CA $1,749 per person
CA $1,749
per person
May 5 - May 11
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Had a great weekend!
Reviewed on Apr 1, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,521, price is now CA $1,146 per person
CA $1,146
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Comfortable, clean room, and you can't beat the view! My favorite thing is relaxing on the chaise lounge, watching the sun rise over Lake Michigan! The food at Lirica is awesome, too.
Reviewed on Apr 1, 2026
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr 5 to Apr 6
CA $151
CA $177 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (10,034 reviews)
Roommates with random people that were loud and tried opening the door connected to our room . No AC , toilet was clogged
Reviewed on Apr 1, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Apr 12 to Apr 13
CA $191
CA $224 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (4,028 reviews)
Nice service and good experience
Reviewed on Apr 1, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Apr 12 to Apr 13
CA $198
CA $233 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,802 reviews)
Positives: The staff was friendly, professional, and very helpful throughout my stay. Negatives: Unfortunately, my experience had a few issues. I didn’t receive the suite I had booked for the first night and had to switch rooms the next day, which was quite inconvenient. The bathroom also had a persistent ...
Reviewed on Apr 1, 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.
Discover the most popular places to visit in Hillside
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Hillside
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
Explore a world of travel with Expedia
- Farmstay in Bellwood
- B&B in Bellwood
- Golf Hotels in Bellwood
- Spa Hotels in Bellwood
- Bellwood Hotels
- Inns in Bellwood
- Motels in Bellwood
- Aparthotels in Berkeley
- B&B in Berkeley
- Guest Houses in Berkeley
- Cheap Hotels in Berkeley
- Luxury Hotels in Berkeley
- Berkeley Hotels
- Inns in Berkeley
- Motels in Berkeley
- Resorts in Berkeley
- Chicago Hotels
- Aparthotels in Elmhurst
- Apartments in Elmhurst
- Chalets in Elmhurst
- Guest Houses in Elmhurst
- Casino Hotels in Elmhurst
- Cheap Hotels in Elmhurst
- Hotels & Resorts for Couples in Elmhurst
- Golf Hotels in Elmhurst
- Historic Hotels in Elmhurst
- Hotels with Hot Tubs in Elmhurst
- Hotels with Kitchenettes in Elmhurst
- Luxury Hotels in Elmhurst
- Pet-Friendly Hotels in Elmhurst
- Spa Hotels in Elmhurst
- Winery Hotels in Elmhurst
- Elmhurst Hotels
- Inns in Elmhurst
- Vacation Homes in Elmhurst
- Resorts in Elmhurst
- Hotels near Elmhurst Station
- Resorts in Elmhurst Station
- Townhomes in Elmhurst
- Hotels near Midwest Conference Center
- Aparthotels in Stone Park
- Hotels & Resorts for Couples in Stone Park
- Lgbt Friendly Hotels in Stone Park
- Spa Hotels in Stone Park
- Stone Park Hotels
- Resorts in Stone Park
- Aparthotels in Westchester
- B&B in Westchester
- Chalets in Westchester
- Guest Houses in Westchester
- Boutique Hotels in Westchester
- Cheap Hotels in Westchester
- Golf Hotels in Westchester
- Hotels with a Pool in Westchester
- Hotels with Bar in Westchester
- Shopping Hotels in Westchester
- Spa Hotels in Westchester
- Westchester Hotels
- Inns in Westchester
- Motels in Westchester
- Resorts in Westchester
- Yorkfield Hotels
- Broadview Vacations
- Burbank Vacations
- Catherine Chevalier Woods
- Chicago Vacations
- Clearing Vacations
- Copernicus Center
- Des Plaines Vacations
- Donald E. Stephens Convention Center
- Elmhurst Vacations
- Ernest Hemingway Museum and House
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Golf Vacations
- Hometown Vacations
- Legoland® Discovery Center
- Lakeview Vacations
- Loretto Hospital
- Melrose Park Vacations
- Monument Park
- Morton Arboretum
- Norma Vacations
- River Forest Vacations
- Rosemont Vacations
- Sleepy Hollow Vacations
- United Center
- Unity Temple
- Wheaton Vacations
- Woodfield Mall
- Wrigley Field
- Yorktown Shopping Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
