Title: Highwood Vacation Packages 2026 from $554 | Expedia.com [Highwood Travel Guide](https://expedia.com/Highwood.dx115190)[Hotels in Highwood](https://expedia.com/Highwood-Hotels.d115190.Travel-Guide-Hotels)[Vacation Rentals in Highwood](https://expedia.com/Highwood-Vacation-Rentals.d115190.Travel-Guide-VacationRentals)[Flights to Highwood](https://expedia.com/Cheap-Flights-To-Highwood.d115190.Travel-Guide-Flights)[Car Rentals in Highwood](https://expedia.com/Car-Rentals-In-Highwood.d115190.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highwood Vacations from $554 ## 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 Highwood Vacation Book a custom vacation package to Highwood and get ready to experience this incredible city how you like. Consider staying in the neighborhood of Riverwoods, which is good for nature and tons more. A trip to Highwood is an excellent opportunity to take in the sights. Be sure to look around renowned 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 [Marriott Theatre](https://www.expedia.com/Marriott-Theatre-Half-Day.d553248621532659125.Vacation-Attraction). No matter your travel plans or the size of your budget, putting together a tailored Highwood vacation is a breeze with Expedia. ## The Latest Highwood 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 Save 100% on your flight $554 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again. Reviewed on Mar 19, 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 Save 100% on your flight $732 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Very central hotel and facilities in excellent condition Reviewed on Mar 22, 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 Save 100% on your flight $680 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,076 reviews) Beautiful, clean, quiet and so comfortable. Reviewed on Mar 22, 2026 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare Save 100% on your flight $610 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.4/10 Very Good! (2,231 reviews) Clean room and friendly staff Reviewed on Mar 21, 2026 ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago Save 100% on your flight $676 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (3,314 reviews) Clean room nice staff, beautiful property. Enjoyed the deluxe room Reviewed on Mar 20, 2026 Don't see what you're looking for? See all available trips from Columbus to Highwood [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-22/2026-04-29/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Highwood ![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 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 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) ![View of Chicago skyline at sunrise.](https://images.trvl-media.com/place/6069213/7912338a-cac5-4762-9012-728b8bea99be.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes 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 Highwood ![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 $26 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission $44 per adult **98%** of travellers recommend [](https://expedia.com/things-to-do/skydeck-willis-tower-admission.a1342523.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 $61 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.activity-details) [See all activities in Highwood](https://expedia.com/things-to-do/search?rid=115190) ## Highwood 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 $217 nightly $255 total Apr 12 - Apr 13 Total with taxes and fees 8.4/10 Very Good! (2,231 reviews) Clean room and friendly staff Reviewed on Mar 21, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=115190) ![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 $127 nightly $144 total Mar 23 - Mar 24 Total with taxes and fees 8.8/10 Excellent! (2,424 reviews) Great hotel! Reviewed on Mar 20, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F23%2F2026&endDate=3%2F24%2F2026&selected=5403&PinnedHotelID=5403&HadPinnedHotel=true®ionId=115190) ![Marriott Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/10000/300/281/c9c2af9c_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 $149 nightly $175 total Apr 3 - Apr 4 Total with taxes and fees 8.6/10 Excellent! (1,234 reviews) They have a shuttle to airport. Very nice hotel. Reviewed on Mar 16, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F3%2F2026&endDate=4%2F4%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true®ionId=115190) [See all 1,480 properties in Highwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F23%2F2026&endDate=3%2F24%2F2026®ionId=115190) 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 Highwood Vacation Packages ## Highwood Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 5,400 | | Max Temp Winter | 30ºF | | Max Temp Summer | 75ºF | | Top Sights | [Genesee Theater](https://www.expedia.com/Genesee-Theater-Chicago.d6142967.Vacation-Attraction), [Marriott Theatre](https://www.expedia.com/Marriott-Theatre-Half-Day.d553248621532659125.Vacation-Attraction) and [North Shore Center for the Performing Arts](https://www.expedia.com/North-Shore-Center-For-The-Performing-Arts-Chicago.d6152652.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 [](https://expedia.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) 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[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](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 Highwood vacation package cost? ### What are the cheapest months to go to Highwood? ### How many days is enough for Highwood? ### How to find the best Highwood package deals? ### Is it cheaper to book a Highwood vacation as a package? ### When to book a vacation package to Highwood? ### Does Expedia offer Book Now, Pay Later Highwood vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Apartments in Highwood Station ](https://www.expedia.com/Highwood-Station-Apartments.d6214844-aaApartments.Travel-Guide-Accommodation) - [Hotels near Highland Park Fort Sheridan Station ](https://www.expedia.com/Highland-Park-Fort-Sheridan-Station-Hotels.d6214846.Travel-Guide-Hotels) - [Condo Rentals in Highland Park Fort Sheridan Station ](https://www.expedia.com/Highland-Park-Fort-Sheridan-Station-Condos.d6214846-aaCondos.Travel-Guide-Accommodation) - [Hotels near Highland Park Country Club 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