Title: Highland Vacation Packages & Trips 2026 from CA $1,158 | 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://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland 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 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. ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago CA $1,158 per person May 8 - May 13 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (2,091 reviews) Clean room and great staff! Reviewed on Mar 24, 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 $1,451 per person Jun 4 - Jun 8 found 23 hours ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The rooftop wasn’t open, everything else was great Reviewed on Mar 24, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,510 per person Jun 4 - Jun 8 found 23 hours ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) This was a nice hotel but some staff made us feel uncomfortable and the rooms had flaws (dirt). I expected better for the money however, I met someone who stayed at Travelodge and their hotel flooded. So, I'd recommend this hotel. Reviewed on Mar 23, 2026 ![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bbf9e380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago CA $1,474 per person Jun 4 - Jun 8 found 23 hours ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,021 reviews) I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans! The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too! The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well! All and all it’s a wonderful place to experience!!!!🍍 Reviewed on Mar 18, 2026 ## Ready to book your vacation to Highland? Choose your dates ## Highland Hotel Deals ![DoubleTree by Hilton Chicago - Alsip](https://images.trvl-media.com/lodging/1000000/30000/25600/25507/fcb66f28_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Chicago - Alsip 5000 W 127th St Alsip IL Fully refundableReserve now, pay when you stay CA $140 CA $295 total Apr 5 - Apr 6 includes taxes & fees 8.4/10 Very Good! (1,015 reviews) Resturant staff was not very friendly and the pool area had teenagers playing football with a real football so staff stepped in and small children were being knocked over in the process. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=25507&PinnedHotelID=25507&HadPinnedHotel=true®ionId=177657) ![Hilton Chicago/Oak Lawn](https://images.trvl-media.com/lodging/1000000/20000/17700/17618/0e1ccba8_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 $156 CA $180 total Apr 5 - Apr 6 includes taxes & fees 8.4/10 Very Good! (1,248 reviews) My stay at Hilton Chicago/Oak Lawn was a bit of a mixed experience. On the positive side, the entry staff were incredibly welcoming and professional, which made a great first impression. The restaurant and bar were also highlights—excellent service, great atmosphere, and definitely enjoyable. However, ... Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=17618&PinnedHotelID=17618&HadPinnedHotel=true®ionId=177657) ![Wind Creek Southland Casino and Hotel](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/1fba48a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wind Creek Southland Casino and Hotel 17300 S Halsted St Hazel Crest IL Fully refundableReserve now, pay when you stay CA $246 CA $275 total Mar 30 - Mar 31 includes taxes & fees 9.4/10 Exceptional! (295 reviews) ALL PERFECT Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=112051593&PinnedHotelID=112051593&HadPinnedHotel=true®ionId=177657) [See all 912 properties in Highland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®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