Hickory Hills Vacation Packages

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Your Hickory Hills Vacation

When a fun city getaway is calling, answer it with a vacation package to Hickory Hills. The neighborhood of Woodlawn, which is great for cycling, golfing and walking, makes a terrific base for your adventures. Want to explore your surroundings? SeatGeek Stadium, Chicago Ridge Shopping Mall and Burr Ridge Village Center are three of the leading places to visit during your trip to Hickory Hills. A couple of quick clicks is all it takes to build your dream Hickory Hills vacation on Expedia.

Top Hickory Hills Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,010, price is now CA $548 per person
CA $548
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.

Reviewed on Sep. 4, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,162, price is now CA $1,287 per person
CA $1,287
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service

Reviewed on Sep. 4, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,126, price is now CA $694 per person
CA $694
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on Sep. 4, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,095, price is now CA $679 per person
CA $679
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
Matthew at the front desk was great & he made our stay better than we could’ve expected. The food from the restaurant was amazing (highly recommend the wings) and the bartenders are wonderful! Our room was a dream! 100/10! ⭐️ We will definitely be returning for our next Chicago stay!

Reviewed on Sep. 5, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,313, price is now CA $821 per person
CA $821
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
Great place esp last minute

Reviewed on Sep. 5, 2025

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Hickory Hills Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Sep 22 to Sep 23
CA $204
CA $240 total
Sep 22 - Sep 23
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Sep 14 to Sep 15
CA $246
CA $288 total
Sep 14 - Sep 15
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Oct 7 to Oct 8
CA $171
CA $226 total
Oct 7 - Oct 8
includes taxes & fees
Freehand Chicago
See all 4,532 properties in Hickory Hills
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.
All Inclusive Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Hickory Hills

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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.

Michigan Avenue
Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Hickory Hills

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
94% of travellers recommend
Color Factory Chicago Ticket
Relax and enjoy the view

Chicago Architecture Center River Cruise aboard First Lady

CA $77
per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
See all activities in Hickory Hills
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.