Title: Hillcrest Vacation Packages & Trips 2026 from CA $507 | Expedia.ca [Hotels in Hillcrest](https://expedia.ca/Hillcrest-Hotels.d553248634983136604.Travel-Guide-Hotels)[Vacation Rentals in Hillcrest](https://expedia.ca/Hillcrest-Vacation-Rentals.d553248634983136604.Travel-Guide-VacationRentals)[Hillcrest Car Rentals](https://expedia.ca/Car-Rentals-In-Hillcrest.d553248634983136604.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Hillcrest Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Rochelle-Railroad-Park-Rochelle.d553248621532658455.Vacation-Attraction) and [Chicagoland Skydiving Center](https://www.expedia.ca/Chicagoland-Skydiving-Center-Rochelle.d553248621532658454.Vacation-Attraction) 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. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $507 per person Feb 17 - Feb 21 found 14 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) Clean rooms, great location in Evanston near the university. Helpful staff. Reviewed on Nov 17, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,902 per person Jan 31 - Feb 6 found 18 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!! Reviewed on Dec 15, 2025 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $808 per person Jan 31 - Feb 6 found 18 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on Dec 4, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $988 per person Feb 23 - Feb 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on Dec 14, 2025 ![Radisson Blu Aqua Hotel Chicago](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Radisson Blu Aqua Hotel Chicago Downtown Chicago CA $725 per person Jan 31 - Feb 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (1,761 reviews) Hotel was amazing all around! Friendly and very helpful staff. Clean rooms and a Starbucks! Reviewed on Dec 14, 2025 ## Ready to book your vacation to Hillcrest? Choose your dates ## Hillcrest Hotel Deals ![Hampton Inn DeKalb, IL](https://images.trvl-media.com/lodging/8000000/7430000/7422200/7422102/w3840h2556x0y4-b392c05f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn DeKalb, IL 663 S. Annie Glidden Road DeKalb IL Fully refundableReserve now, pay when you stay CA $157 CA $178 total Dec 31 - Jan 1, 2026 includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) Room was fine. Staff was courteous. Reviewed on Dec 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=7422102&PinnedHotelID=7422102&HadPinnedHotel=true®ionId=553248634983136604) ![Home2 Suites by Hilton Dekalb](https://images.trvl-media.com/lodging/56000000/55270000/55262900/55262856/d97caa7a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Home2 Suites by Hilton Dekalb 575 S ANNIE GLIDDEN RD DeKalb IL Fully refundableReserve now, pay when you stay CA $175 CA $199 total Dec 26 - Dec 27 includes taxes & fees 9.2/10 Wonderful! (403 reviews) Front desk guy was solid Reviewed on Dec 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F12%2F2025&endDate=27%2F12%2F2025&selected=55262856&PinnedHotelID=55262856&HadPinnedHotel=true®ionId=553248634983136604) ![Country Inn & Suites by Radisson, Sycamore, IL](https://images.trvl-media.com/lodging/1000000/550000/548400/548376/265ce585_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Sycamore, IL 1450 South Peace Road Sycamore IL Fully refundable CA $127 CA $141 total Jan 5 - Jan 6, 2026 includes taxes & fees 8.4/10 Very Good! (937 reviews) Clean room. Friendly staff. Little dated Reviewed on Dec 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=548376&PinnedHotelID=548376&HadPinnedHotel=true®ionId=553248634983136604) [See all 64 properties in Hillcrest](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248634983136604) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app