Hillcrest Vacation Packages
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Your Hillcrest Vacation
Unforgettable adventures await when you book a vacation package to Hillcrest. Whether you're a foodie, art buff or just a traveler who loves experiencing new places, there's something for everyone in this vibrant city. Every good trip to Hillcrest should include some sightseeing. What to do first? Rochelle Railroad Park and Chicagoland Skydiving Center are major attractions. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Hillcrest vacation is a breeze with Expedia.
Top Hillcrest 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 $1,351, price is now CA $876 per person
CA $876
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay
Reviewed on Apr 7, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,459, price is now CA $928 per person
CA $928
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The room was clean. Very modern hotel. Great service and staff. Great experience overall.
Reviewed on Apr 7, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,474, price is now CA $1,010 per person
CA $1,010
per person
Jul 2 - Jul 5
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,334, price is now CA $2,301 per person
CA $2,301
per person
May 15 - May 19
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
Cambria Hotel Chicago Loop - Theatre District
Downtown Chicago
Price was CA $1,784, price is now CA $1,242 per person
CA $1,242
per person
May 14 - May 18
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,551 reviews)
Clean room
Nice music mirror
Reviewed on Apr 6, 2026
Hillcrest Hotel Deals
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Apr 13 to Apr 14
CA $179
CA $203 total
Apr 13 - Apr 14
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
Always a great stay
Reviewed on Apr 5, 2026
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Apr 15 to Apr 16
CA $123
CA $136 total
Apr 15 - Apr 16
includes taxes & fees
8.2/10 Very Good! (405 reviews)
We really enjoyed our stay at this Best Western. Hot breakfast with protein everyday. Every staff member from desk to housekeeper were the friendliest we have ever encountered at a motel! Comfortable bed in rooms with mood lighting. I can’t say enough good about our stay. The entrance drive into ...
Reviewed on Mar 21, 2026
Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Apr 30 to May 1
CA $182
CA $206 total
Apr 30 - May 1
includes taxes & fees
9.2/10 Wonderful! (434 reviews)
Nice staff because their in the lovely town od Dekalb which is filled with the most pleasant folks ever! Also breakfast with the sausage gravy amazing and had a great comfortable stay!
Reviewed on Apr 5, 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.
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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.
