Title: Cortland Vacation Packages & Trips 2026 from CA $645 | Expedia.ca [Hotels in Cortland](https://expedia.ca/Cortland-Hotels.d553248634983538003.Travel-Guide-Hotels)[Vacation Rentals in Cortland](https://expedia.ca/Cortland-Vacation-Rentals.d553248634983538003.Travel-Guide-VacationRentals)[Cortland Car Rentals](https://expedia.ca/Car-Rentals-In-Cortland.d553248634983538003.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) # Cortland 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 Cortland Vacation Excellent adventures await when you reserve a vacation package to Cortland. Whether you're a foodie, art enthusiast or just a traveler who loves experiencing new places, there's something for everyone in this lively city. Make your trip to Cortland even more exciting by including some sightseeing. [Northern Illinois University](https://www.expedia.ca/Northern-Illinois-University-DeKalb.d6091397.Vacation-Attraction), [Huskie Stadium](https://www.expedia.ca/Huskie-Stadium-DeKalb.d6091399.Vacation-Attraction) and [Ellwood House Museum](https://www.expedia.ca/Ellwood-House-Museum-DeKalb.d553248621532658460.Vacation-Attraction) are some of the big attractions worth exploring. Don't put off exploring this city any longer. Your ultimate Cortland vacation is a couple of clicks away with Expedia. ## Top Cortland Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago CA $645 per person Apr 24 - Apr 27 found 23 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,003 reviews) Staff was great. The hotel is quirky and cool with an unbeatable location right in the middle of shopping, theater and restaurants. Easily walkable to the Art Institute and Millennium Park. The rooms are not large, and could use some new furniture, but very clean. Will definitely be back. Reviewed on Feb 14, 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 $811 per person Apr 24 - Apr 27 found 23 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean rooms, clean hotel, friendly staff. Reviewed on Feb 15, 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 ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wade Downtown Chicago CA $757 per person Apr 10 - Apr 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.4/10 Very Good! (1,444 reviews) I had a great stay at the Wade Hotel in Chicago! The room was very clean and comfortable, and the staff was friendly, professional, and welcoming from check-in to check-out. The amenities were convenient, and the location made it easy to get around the city. I would definitely stay here again and recommend it to anyone visiting Chicago. Reviewed on Feb 9, 2026 ![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 $660 per person Apr 24 - Apr 27 found 23 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9/10 Wonderful! (766 reviews) I would definitely stay here again Reviewed on Feb 15, 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_553248634983538003) ## Ready to book your vacation to Cortland? Choose your dates ## Cortland Hotel Deals ![Quality Inn and Suites St Charles - West Chicago](https://images.trvl-media.com/lodging/1000000/180000/171200/171194/2322de6b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn and Suites St Charles - West Chicago 1600 E Main St St. Charles IL Fully refundableReserve now, pay when you stay CA $82 CA $92 total Mar 17 - Mar 18 includes taxes & fees 8.2/10 Very Good! (1,001 reviews) The room was very clean and bathroom nicely updated. The front desk clerk had a difficult time finding a room for me. I stood there for several minutes while they searched your computer for a room that had been cleaned at 4 pm in the afternoon. She was very professional and friendly but you need ... Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F03%2F2026&endDate=18%2F03%2F2026&selected=171194&PinnedHotelID=171194&HadPinnedHotel=true®ionId=553248634983538003) ![Hampton Inn & Suites Chicago/Aurora](https://images.trvl-media.com/lodging/1000000/700000/691200/691142/ad5383da_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Chicago/Aurora 2423 Bushwood Dr Aurora IL Fully refundableReserve now, pay when you stay CA $174 CA $195 total Mar 5 - Mar 6 includes taxes & fees 9.2/10 Wonderful! (1,003 reviews) Very good.. staff was great, nice location Reviewed on Feb 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=691142&PinnedHotelID=691142&HadPinnedHotel=true®ionId=553248634983538003) ![Comfort Inn & Suites North Aurora - Naperville](https://images.trvl-media.com/lodging/1000000/700000/696400/696344/e1014d34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites North Aurora - Naperville 308 S Lincolnway Street North Aurora IL Fully refundableReserve now, pay when you stay CA $108 CA $117 total Feb 22 - Feb 23 includes taxes & fees 8/10 Very Good! (856 reviews) Everything was clean. Breakfast was good. Only issue was that the fire alarm went off at 5am and there was no direction or information that all was clear. We stayed 3 nights and other two were fine. Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=696344&PinnedHotelID=696344&HadPinnedHotel=true®ionId=553248634983538003) [See all 141 properties in Cortland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F02%2F2026&endDate=18%2F02%2F2026®ionId=553248634983538003) 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