Title: Leland Vacation Packages & Trips 2025/2026 from CA $644 | Expedia.ca [Hotels in Leland](https://expedia.ca/Leland-Hotels.d553248634983185916.Travel-Guide-Hotels)[Vacation Rentals in Leland](https://expedia.ca/Leland-Vacation-Rentals.d553248634983185916.Travel-Guide-VacationRentals)[Leland Car Rentals](https://expedia.ca/Car-Rentals-In-Leland.d553248634983185916.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) # Leland 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 ## Top Leland Vacation Deals Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $644 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=XXfGMEiZ2_ele01-IfRLtudYv6qWX3LsMD1Yb5nWKjoh4SAkXuTHx77BEW1jpIW2) ![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 $822 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=XXfGMEiZ2_ele01-IfRLtj0ugZmND9lDt1Yrk9O6qHYGu3I7RMb5iMiD5F5fuNTy) ![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 $1,389 per person Jan 2 - Jan 7 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) Great staff, very clean rooms, overall great experience Reviewed on Oct 31, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-07/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=otRewe5h8bOrTlw8BroZ5nVGA4VA63HHwnaKx-Asxkb25kVsIOGLQybiEmoN2Jmy) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $908 per person Jan 2 - Jan 7 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) Always a great stay! Staff are great and rooms present great value. Reviewed on Nov 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-07/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=otRewe5h8bOrTlw8BroZ5ltEQoWd4eAOYIW-WXoHK08SmTEKPjhfzc1bCjP6gc8n) ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago CA $689 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,852 reviews) Great location. Comfortable room and wonderful service. Reviewed on Oct 31, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26910691&paandie=true&dealMarker=XXfGMEiZ2_ele01-IfRLtiIfClvaVR63Z3JwKSFopfK9RVPHRvBpiYdDLGoBQnrF) ## Ready to book your vacation to Leland? Choose your dates ## Leland Hotel Deals ![Grand Bear Resort at Starved Rock](https://images.trvl-media.com/lodging/2000000/1510000/1500900/1500830/c6b13292_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grand Bear Resort at Starved Rock 2643 IL-178, Utica, IL Fully refundableReserve now, pay when you stay CA $150 CA $172 total Nov 4 - Nov 5 includes taxes & fees 7.2/10 Good! (986 reviews) Room was good but the some of the electrical plugs didn’t work Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F11%2F2025&endDate=05%2F11%2F2025&selected=1500830&PinnedHotelID=1500830&HadPinnedHotel=true®ionId=553248634983185916) ![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 $159 CA $181 total Dec 3 - Dec 4 includes taxes & fees 9.2/10 Wonderful! (984 reviews) none Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&selected=7422102&PinnedHotelID=7422102&HadPinnedHotel=true®ionId=553248634983185916) ![Holiday Inn Express & Suites Yorkville by IHG](https://images.trvl-media.com/lodging/43000000/42010000/42005500/42005490/79683caa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express & Suites Yorkville by IHG 577 E KENDALL DRIVE, Yorkville, IL Fully refundable CA $113 CA $127 total Nov 16 - Nov 17 includes taxes & fees 8.2/10 Very Good! (608 reviews) The Spa was down again for 2 days of our stay. However they got it fixed in a timely manner & Dave @ the front desk was pleasant & made our stay more enjoyable. Reviewed on Oct 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=42005490&PinnedHotelID=42005490&HadPinnedHotel=true®ionId=553248634983185916) [See all 329 properties in Leland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®ionId=553248634983185916) 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 ![QR code to download the app](data:image/png;base64,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)