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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $788, price is now CA $477 per person
CA $477
per person
Nov 21 - Nov 24
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
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was CA $894, price is now CA $580 per person
CA $580
per person
Nov 21 - Nov 24
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
The Langham, Chicago
Downtown Chicago
Price was CA $1,759, price is now CA $1,171 per person
CA $1,171
per person
Oct 28 - Oct 31
found 14 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Hillcrest Hotel Deals
Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road, Sycamore, IL
Fully refundable
The price is CA $129 per night from Sep 8 to Sep 9
CA $129
CA $143 total
Sep 8 - Sep 9
includes taxes & fees
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road, DeKalb, IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Sep 28 to Sep 29
CA $168
CA $191 total
Sep 28 - Sep 29
includes taxes & fees
Super 8 by Wyndham Rochelle
601 E Highway 38, Rochelle, IL
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Sep 16 to Sep 17
CA $92
CA $102 total
Sep 16 - Sep 17
includes taxes & fees
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.
