Hillside Vacation Packages
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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.
Top Hillside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,248, price is now CA $841 per person
CA $841
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.
Reviewed on Jul 1, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,393, price is now CA $1,698 per person
CA $1,698
per person
Sep 1 - Sep 6
found 10 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,612, price is now CA $1,188 per person
CA $1,188
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.
Reviewed on Jun 30, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,154, price is now CA $852 per person
CA $852
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
My husband and I and my daughter in law stayed at the omni because my son was having surgery at northwestern hospital. Is surgery was at 7:30 am and lasted almost 8 hours check in was not until 4, but they really understood our situation they were able to get into our room at noon. So we can rest. Everyone from the greeders at the door the front desk was tremendously helpful in our situation. A room was clean, check-up process with so easy.I highly recommend staying at this hotel.
Reviewed on Jul 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 $211 per night from Jul 2 to Jul 3
CA $211
CA $251 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very good! (10,185 reviews)
"This place was really horrible! The shower was cold as hell and the front desk didn't do anything to help. The room was not wiped down properly and I left first thing on the A.M. when I told the front desk about my stay, they did nothing to fix the issue or reimburse me a portion of my money. I came ..."
Reviewed on Jul 1, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,825 reviews)
"My husband and I and my daughter in law stayed at the omni because my son was having surgery at northwestern hospital. Is surgery was at 7:30 am and lasted almost 8 hours check in was not until 4, but they really understood our situation they were able to get into our room at noon. So we can rest. ..."
Reviewed on Jul 1, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Jul 6 to Jul 7
CA $268
CA $319 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,475 reviews)
"The hotel was beautiful. My issue is that while we were out, the cleaning staff opened a window that opens directly outside with no screen. The window was approx 2.5 ft high and we were 22 floors up. I have an infant that crawled to the window before I knew what was happening. Thank god nothing happened ..."
Reviewed on Jul 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.
What to do in Hillside
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Frequently asked questions
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- Visit Downtown Chicago
- Buckingham Fountain
- Grant Park
- The Loop Vacations
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- Chicago Theatre
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- Woodfield Mall
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- Legoland® Discovery Center
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- International Museum of Surgical Science
- Unity Temple
- Chicago Vacations
- Chicago Riverwalk
- Navy Pier
- Lincoln Park Zoo
- Art Institute of Chicago
- Robie House
- Ernest Hemingway Museum and House
- Golf Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
