Title: Hillcrest Vacation Packages & Trips 2026 from CA $732 | 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. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $732 per person Apr 13 - Apr 17 found 18 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9/10 Wonderful! (766 reviews) The room was very clean. The building was very clean great view lots of activities to do inside of the building as well. We will be going back soon. Reviewed on Feb 16, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,348 per person Apr 1 - Apr 4 found 20 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on Jan 26, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $996 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) The room was excellent Reviewed on Feb 16, 2026 ![Holiday Inn Chicago North-Evanston by IHG](https://images.trvl-media.com/lodging/1000000/10000/5400/5356/a2066909_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Chicago North-Evanston by IHG Downtown Evanston CA $769 per person Apr 24 - Apr 30 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.6/10 Excellent! (1,652 reviews) Comfortable bed, clean room, nice hotel Reviewed on Feb 12, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $912 per person Apr 20 - Apr 24 found 18 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! Reviewed on Feb 2, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248634983136604) ## 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 $133 CA $150 total Feb 23 - Feb 24 includes taxes & fees 9.4/10 Exceptional! (1,001 reviews) Room was clean and breakfast was good! Always a good stay when we are there! Reviewed on Feb 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=7422102&PinnedHotelID=7422102&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 CA $114 CA $126 total Feb 23 - Feb 24 includes taxes & fees 8.4/10 Very Good! (969 reviews) Room was great. Place is undergoing a MUCH NEEDED renovation. Reviewed on Feb 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=548376&PinnedHotelID=548376&HadPinnedHotel=true®ionId=553248634983136604) ![Best Western Sycamore Inn](https://images.trvl-media.com/lodging/1000000/70000/67500/67418/d32c4bf5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Sycamore Inn 1935 Dekalb Ave Sycamore IL Fully refundableReserve now, pay when you stay CA $113 CA $126 total Feb 17 - Feb 18 includes taxes & fees 8.2/10 Very Good! (391 reviews) great room Reviewed on Feb 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=67418&PinnedHotelID=67418&HadPinnedHotel=true®ionId=553248634983136604) [See all 67 properties in Hillcrest](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F02%2F2026&endDate=18%2F02%2F2026®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