Title: Highland Park Vacation Packages 2026 from $430 | Expedia.com [Highland Park Travel Guide](https://expedia.com/Highland-Park.dx8345)[Hotels in Highland Park](https://expedia.com/Highland-Park-Hotels.d8345.Travel-Guide-Hotels)[Vacation Rentals in Highland Park](https://expedia.com/Highland-Park-Vacation-Rentals.d8345.Travel-Guide-VacationRentals)[Flights to Highland Park](https://expedia.com/Cheap-Flights-To-Highland-Park.d8345.Travel-Guide-Flights)[Things to do in Highland Park](https://expedia.com/Things-To-Do-In-Highland-Park.d8345.Travel-Guide-Activities)[Car Rentals in Highland Park](https://expedia.com/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 Vacations from $430 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Chicago-Botanic-Garden-Chicago.d6064029.Vacation-Attraction), [Lake Forest College](https://www.expedia.com/Lake-Forest-College-Chicago.d6156570.Vacation-Attraction) and [Northbrook Sports Complex](https://www.expedia.com/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. ## The Latest Highland Park vacation packages Price found within the past 48 hours. Click for updated prices. ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago $430 per person Jun 11 - Jun 14 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent. Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value 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 $549 per person Jun 11 - Jun 14 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Great location! Excellent customer service! My only one complaint is that there are no microwaves at this property. Reviewed on Mar 26, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago $640 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,076 reviews) Everything was perfect Reviewed on Mar 26, 2026 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago Save 100% on your flight $540 per person Jun 12 - Jun 16 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,675 reviews) We loved our stay. Two adults and our eight-year-old son took a weekend trip to Chicago. This hotel was very close to the field museum and walking distance to magnificent mile. Short Uber ride to nearby shopping and Willis Tower. The staff were awesome and upgraded our room at a low price. We felt very safe and staff were very helpful. The eighth floor had a beautiful pool, spa and sauna, great view of lake mi, open late too. We dined for breakfast at yoke and Niu B for dinner. Delicious. At checkout we purchased a future Hilton grand vacation at a great discount too. Let’s go. :) Reviewed on Mar 25, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago Save 100% on your flight $704 per person Jun 18 - Jun 21 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9/10 Wonderful! (441 reviews) Staff was really nice Reviewed on Mar 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Highland Park [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-26/2026-05-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Highland Park ![Wrigley Field featuring cbd, a sporting event and a city](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 4.5/5(2,149 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.com/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 4.5/5(336 reviews) 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.com/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Chicago Skyline at North Beach](https://images.trvl-media.com/place/6069213/e3e08680-ba57-4e08-8e19-fef490757e5e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes 4.5/5(461 reviews) After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. [](https://expedia.com/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction) ### What to do in Highland Park ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck $27 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Bulls Basketball Game at United Center $66 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.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 $41 per adult **94%** of travellers recommend [](https://expedia.com/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) [See all activities in Highland Park](https://expedia.com/things-to-do/search?rid=8345) ## Highland Park Hotel Deals ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_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 $221 nightly $259 total Apr 26 - Apr 27 Total with taxes and fees 8.4/10 Very Good! (2,244 reviews) Everything was clean and the staff was very friendly and helpful! Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=8345) ![The Chicago Hotel Collection Ambassador Gold Coast](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Chicago Hotel Collection Ambassador Gold Coast 1301 N State Pkwy Chicago IL Fully refundableReserve now, pay when you stay $125 nightly $146 total Mar 29 - Mar 30 Total with taxes and fees 8.2/10 Very Good! (1,323 reviews) Lobby is beautiful and the check in was smooth; however the room was not great. Dingy, dated, poorly set up- only outlet by the bed was connected to the large, blaring overhead light, so once turned off the outlet stopped functioning. Bathroom was dated and cramped with min counter space. Sheets ... Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=17809&PinnedHotelID=17809&HadPinnedHotel=true®ionId=8345) ![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/2c5e0afa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency O'Hare Chicago 9300 Bryn Mawr Ave Rosemont IL Fully refundableReserve now, pay when you stay $135 nightly $154 total Apr 6 - Apr 7 Total with taxes and fees 8.8/10 Excellent! (2,429 reviews) Clean great shuttle service Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=5403&PinnedHotelID=5403&HadPinnedHotel=true®ionId=8345) [See all 2,699 properties in Highland Park](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F27%2F2026&endDate=3%2F28%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. ## Find the Best Highland Park Vacation Packages ## Highland Park Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 29,700 | | Max Temp Winter | 30ºF | | Max Temp Summer | 75ºF | | Top Sights | [Marriott Theatre](https://www.expedia.com/Marriott-Theatre-Half-Day.d553248621532659125.Vacation-Attraction), [North Shore Center for the Performing Arts](https://www.expedia.com/North-Shore-Center-For-The-Performing-Arts-Chicago.d6152652.Vacation-Attraction) and [Kohl Childrens Museum](https://www.expedia.com/Kohl-Childrens-Museum-Chicago.d6186137.Vacation-Attraction) | ## More vacations you might like ![](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.com/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 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Highland Park vacation package cost? ### What are the cheapest months to go to Highland Park? ### How many days is enough for Highland Park? ### Is it worth booking a vacation package to Highland Park? ### How to find the best Highland Park package deals? ### Is it cheaper to book a Highland Park vacation as a package? ### When to book a vacation package to Highland Park? ### How to plan a trip to Highland Park? > 1. Pick the right time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Highland Park. > 2. Set a budget: Consider costs such as flights, food and transportation when working out how much to set aside for your trip to Highland Park. Then, select a hotel that works with your budget, whether that's an affordable option or a deluxe retreat. > 3. Organize your Highland Park escape with Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning): Search for and book stays and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Highland Park together. > 4. Decide how long to go away for: Now that you know more about Highland Park, you can work out the right length of your break. Put together a rough plan and give yourself enough time to get through everything on your must-do list. > 5. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Highland Park vacation package. > 6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Highland Park's highlights. 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