Title: Highland Park Vacation Packages & Trips 2026 from CA $650 | Expedia.ca [Hotels in Highland Park](https://expedia.ca/Highland-Park-Hotels.d8345.Travel-Guide-Hotels)[Vacation Rentals in Highland Park](https://expedia.ca/Highland-Park-Vacation-Rentals.d8345.Travel-Guide-VacationRentals)[Things to do in Highland Park](https://expedia.ca/Things-To-Do-In-Highland-Park.d8345.Travel-Guide-Activities)[Highland Park Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Park.d8345.Car-Rental-Guide) ![](https://images.trvl-media.com/place/8345/95f70157-20d9-4815-9c33-0d43dec32592.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland Park 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 Park Vacation Planning your next big adventure is a piece of cake with a Highland Park vacation package. The neighborhood of Riverwoods, which is great for nature, makes a superb base to uncover the marvels of this unique city. If sightseeing is part of the plan during your trip to Highland Park, check out well-known attractions like [Chicago Botanic Garden](https://www.expedia.ca/Chicago-Botanic-Garden-Chicago.d6064029.Vacation-Attraction), [Lake Forest College](https://www.expedia.ca/Lake-Forest-College-Chicago.d6156570.Vacation-Attraction) and [Northbrook Sports Complex](https://www.expedia.ca/Northbrook-Sports-Complex-Chicago.d6186877.Vacation-Attraction). Whoever you're escaping with and whatever you plan to spend, your dream Highland Park vacation is just clicks away with Expedia. ## Top Highland Park Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Chicago – Midway Airport S by IHG West Lawn CA $650 per person May 3 - May 8 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 8.4/10 Very Good! (1,000 reviews) Staff very friendly Reviewed on Feb 4, 2026 ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel CA $673 per person Apr 22 - Apr 25 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 26, 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 $1,002 per person Apr 25 - Apr 29 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Modern Style Spacious Rooms with an Amazing complimentary breakfast every morning. Reviewed on Feb 9, 2026 ![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 $1,033 per person Mar 13 - Mar 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on Feb 3, 2026 ![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 $1,188 per person Mar 26 - Mar 31 found 1 day ago Roundtrip flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on Jan 31, 2026 ## Ready to book your vacation to Highland Park? Choose your dates ## Highland Park Hotel Deals ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL Fully refundableReserve now, pay when you stay CA $279 CA $328 total Mar 7 - Mar 8 includes taxes & fees 8.2/10 Very Good! (2,215 reviews) A very good value. A bit worn, great bed but half the price of the Westin Denver airport. Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F03%2F2026&endDate=08%2F03%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=8345) ![Marriott Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/10000/300/281/13bbda80_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott Chicago O'Hare 8535 West Higgins Road Chicago IL Fully refundableReserve now, pay when you stay CA $196 CA $230 total Feb 27 - Feb 28 includes taxes & fees 8.6/10 Excellent! (1,218 reviews) aa Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true®ionId=8345) ![Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG](https://images.trvl-media.com/lodging/1000000/30000/20400/20348/9004f7ac_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG 5440 N River Rd Rosemont IL Fully refundable CA $161 CA $184 total Feb 16 - Feb 17 includes taxes & fees 8.6/10 Excellent! (2,731 reviews) Very nice Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=20348&PinnedHotelID=20348&HadPinnedHotel=true®ionId=8345) [See all 2,723 properties in Highland Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F02%2F2026&endDate=11%2F02%2F2026®ionId=8345) 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) ### Discover the most popular places to visit in Highland Park ![Wrigley Field featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### What to do in Highland Park ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour CA $55 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $46 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Highland Park](https://expedia.ca/things-to-do/search?rid=8345) ## 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