Title: Highland Vacation Packages & Trips 2025/2026 from CA $674 | Expedia.ca [Hotels in Highland](https://expedia.ca/Highland-Hotels.d177657.Travel-Guide-Hotels)[Vacation Rentals in Highland](https://expedia.ca/Highland-Vacation-Rentals.d177657.Travel-Guide-VacationRentals)[Things to do in Highland](https://expedia.ca/Things-To-Do-In-Highland.d177657.Travel-Guide-Activities)[Highland Car Rentals](https://expedia.ca/Car-Rentals-In-Highland.d177657.Car-Rental-Guide) ![](https://images.trvl-media.com/place/177657/87fb36ed-26eb-46b0-a77d-72c76798465e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Joe Farmer - ## 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 Highland Vacation Spend less time travel planning and more time having exciting adventures with a Highland vacation package. The neighborhood of East Side, which is good for nature and walking, makes an excellent base for your city break. Like to get out and explore? [Hard Rock Casino Northern Indiana](https://www.expedia.ca/Hard-Rock-Casino-Northern-Indiana-Gary.d689582177477787648.Vacation-Attraction), [Purdue University Northwest](https://www.expedia.ca/Purdue-University-Northwest-Hammond.d553248622008968181.Vacation-Attraction) and [Hammond Sportsplex & Community Center](https://www.expedia.ca/Hammond-Sportsplex-Community-Center-Hammond.d620049903162130432.Vacation-Attraction) are three of the leading places to visit during your trip to Highland. Don't delay your visit to this destination any longer. Your ultimate Highland vacation is only a few clicks away with Expedia. ## Top Highland Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hampton Inn & Suites Chicago Medical District UIC](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/03795c9c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Chicago Medical District UIC Near West Side CA $674 per person Dec 31 - Jan 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.6/10 Exceptional! (246 reviews) Clean room comfy beds and pillows Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-06/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102236658&paandie=true&dealMarker=ECE-TDp9fdBR_p-FML9EkQSbCdKfpQb2AtsH183DipnqXgrfBCKJ-G83hC_jUBtj) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $1,071 per person Dec 21 - Dec 26 found 24 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 8.8/10 Excellent! (1,046 reviews) One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-26/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=eQ41785sc6bOv5L8pbLHTuZJkd3-vlTCF_ETDWtV-v3ZQLaPkgqG0v45Qs0Krbu4) ![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 $1,706 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 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=1723215&paandie=true&dealMarker=nydeEVrW5r1JKFwu4YZKCtS-_LS-boMiioQfXFRXTZrJ_Qm9nDmq1ZdV6MYTpL9r) ![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 $1,034 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 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=nydeEVrW5r1JKFwu4YZKCsH6Yi5FZ0jNasJosixS5h6dK2WCrh2bFo56SxhlnfXw) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,073 per person Dec 17 - Dec 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-17/2025-12-20/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=j-wMUwZ57PH9L72rnYZbVl8xSdy3u7D--Qyg0DSvwJnjMDiTggngBLZISNXBJhNL) ## Ready to book your vacation to Highland? Choose your dates ## Highland Hotel Deals ![Hilton Chicago/Oak Lawn](https://images.trvl-media.com/lodging/1000000/20000/17700/17618/6279b55c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Oak Lawn 9333 S Cicero Ave, Oak Lawn, IL Fully refundableReserve now, pay when you stay CA $173 CA $199 total Oct 22 - Oct 23 includes taxes & fees 8.2/10 Very Good! (1,066 reviews) "The staff was super helpful and sweethearts!" Reviewed on Oct 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F10%2F2025&endDate=23%2F10%2F2025&selected=17618&PinnedHotelID=17618&HadPinnedHotel=true®ionId=177657) ![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 - Chicago, IL 10022 South Halsted Street, Chicago, IL Fully refundableReserve now, pay when you stay CA $95 CA $111 total Oct 19 - Oct 20 includes taxes & fees 6.6/10 (136 reviews) "Everything was very nice even staff" Reviewed on Oct 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=115871645&PinnedHotelID=115871645&HadPinnedHotel=true®ionId=177657) ![Ameristar Casino Hotel East Chicago](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ameristar Casino Hotel East Chicago 777 Ameristar Blvd., East Chicago, IN Fully refundableReserve now, pay when you stay CA $197 CA $234 total Oct 20 - Oct 21 includes taxes & fees 8.4/10 Very Good! (1,018 reviews) "Soaker tub" Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=20%2F10%2F2025&endDate=21%2F10%2F2025&selected=2518162&PinnedHotelID=2518162&HadPinnedHotel=true®ionId=177657) [See all 860 properties in Highland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=177657) 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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)