Title: Highwood Vacation Packages 2026 from $460 | 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 $460 ## 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. ![Illinois Beach Hotel](https://images.trvl-media.com/lodging/84000000/83570000/83567200/83567194/bc5aabfe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Illinois Beach Hotel Save 100% on your flight $460 per person Jun 23 - Jun 28 found 24 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 8/10 Very Good! (504 reviews) Everything is fine clean the view 👌 Reviewed on Mar 29, 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 Jun 19 - Jun 22 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back Reviewed on Apr 1, 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 $533 per person Jun 12 - Jun 15 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 ![Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/5a40507c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination Save 100% on your flight $548 per person Jun 12 - Jun 15 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 8.4/10 Very Good! (999 reviews) Beautiful rooms and casino i cant wait to return Reviewed on Mar 2, 2026 ![Hilton Garden Inn Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Downtown South Loop Downtown Chicago Save 100% on your flight $560 per person Jun 12 - Jun 15 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.8/10 Excellent! (1,894 reviews) I would not recommend this property. It is very loud. The shower head dripped on the metal pan in the base of the shower all day and night. Additionally, the room is very dark. Reviewed on Apr 1, 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/2026-05-01/2026-05-08/?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](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) ![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) ![Navy Pier](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4.5/5(4,923 reviews) A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.com/Navy-Pier-Downtown-Chicago.d6069215.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 $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) ![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Navy Pier Centennial Wheel Ticket $25 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.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 $221 nightly $259 total May 2 - May 3 Total with taxes and fees 8.4/10 Very Good! (2,242 reviews) The hotel environment is very nice. Clean room，friendly staff Reviewed on Apr 1, 2026 [](https://expedia.com/Hotel-Search?startDate=5%2F2%2F2026&endDate=5%2F3%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 $135 nightly $154 total Apr 4 - Apr 5 Total with taxes and fees 8.8/10 Excellent! (2,449 reviews) Very thin walls could hear a child crying all night. There was a huge gap on my door. You could see clearly outside without opening the door. Reviewed on Apr 1, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F4%2F2026&endDate=4%2F5%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 $159 nightly $187 total Apr 3 - Apr 4 Total with taxes and fees 8.6/10 Excellent! (1,232 reviews) The poolside sitting area was limited & very slippery had to be extra cautious. Reviewed on Mar 30, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F3%2F2026&endDate=4%2F4%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true®ionId=115190) [See all 1,484 properties in Highwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F2%2F2026&endDate=4%2F3%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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