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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,543, price is now CA $1,017 per person
CA $1,017
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Very quiet, really clean and staff was great
Reviewed on Apr 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,627, price is now CA $1,724 per person
CA $1,724
per person
May 5 - May 11
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
Hotel Chicago Downtown, Autograph Collection by Marriott
Downtown Chicago
Price was CA $1,944, price is now CA $1,327 per person
CA $1,327
per person
May 5 - May 11
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Nice hotel with friendly staff! Housekeeping very helpful and kind. It does seem the front desk was understaffed for the size of hotel and how busy it was. Was hard to get call answered when phoned desk.
Reviewed on Mar 30, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,669, price is now CA $1,205 per person
CA $1,205
per person
May 5 - May 11
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,503 reviews)
The staff was very friendly. We were needy in our room and needed more coffee and more blankets and they brought them up so quickly and were so polite. The staff always said hi and goodbye when we walked through the lobby. They always greeted us with a smile.
Reviewed on Apr 2, 2026
Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Apr 5 to Apr 6
CA $150
CA $177 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (10,007 reviews)
Good location for where we needed to be in the city. It’s a very dated hotel.
Reviewed on Apr 2, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Apr 5 to Apr 6
CA $180
CA $211 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (4,039 reviews)
The toliet was loose in the bathroom
Reviewed on Apr 2, 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 $199 per night from Apr 12 to Apr 13
CA $199
CA $233 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,808 reviews)
The breakfast changes everyday. My kids enjoyed the stay. Its close to a lot of good places. Front desk staff was very friendly :)
Reviewed on Apr 2, 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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
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
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
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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.
