Title: Leland Vacation Packages & Trips 2025/2026 from CA $548 | 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. ![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 $548 per person Jan 16 - Jan 19 found 1 hour 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/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=EdX7Rh5nPMXgi2lS0rhe8psnBAaQgZFhkrLDZ7yCOuVqshv2xh3nuaboYdplWaWs) ![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 $1,045 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) Really cool modern space Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=_5ljSQ6woMY7TAVHTy4I2O6mVtiaRpSAKZexmmW9xRxC3nj8ZvPpRHeZDE6idQ_b) ![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 $1,183 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (367 reviews) This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom. The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine. Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters. Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=Br8uQJZB120LWEepv4T_RTr-IRYWZDByuz1WO1rMQzcPPO2SEsnCCraEPEz336uP) ![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 $785 per person Jan 16 - Jan 19 found 1 hour ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property. Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=EdX7Rh5nPMXgi2lS0rhe8psnBAaQgZFhkrLDZ7yCOuURMJHL1a8OxYPN0GoQizAy) ![The Blackstone, Autograph Collection](https://images.trvl-media.com/lodging/1000000/30000/22300/22295/5f1a18d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Blackstone, Autograph Collection Downtown Chicago CA $869 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,003 reviews) Best location to stay Reviewed on Oct 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=22295&paandie=true&dealMarker=Br8uQJZB120LWEepv4T_RX53k6b2KWTqgkVzZm258KiNhADBr1wVHOeSgVXgisQp) ## 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 CA $153 CA $175 total Nov 10 - Nov 11 includes taxes & fees 7.2/10 Good! (990 reviews) The check in desk was very nice . The room was nice and spacious but the bathroom was very small. The tv was small and had a very limited selection with no ability to stream any apps on the tv. The restaurant, jacks place had an extremely limited menu and the quality was lacking. The food was fresh ... Reviewed on Nov 1, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%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 $168 CA $191 total Nov 13 - Nov 14 includes taxes & fees 9.2/10 Wonderful! (984 reviews) none Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F11%2F2025&endDate=14%2F11%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 $111 CA $124 total Nov 16 - Nov 17 includes taxes & fees 8.2/10 Very Good! (609 reviews) Big rooms Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=42005490&PinnedHotelID=42005490&HadPinnedHotel=true®ionId=553248634983185916) [See all 328 properties in Leland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F11%2F2025&endDate=06%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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)