Title: Highwood Vacation Packages 2026 from $647 | 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 $647 ## 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. ![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 $647 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) Staff was soooo friendly Reviewed on Mar 25, 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 $698 per person May 8 - May 13 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Service was terrific in every way! Warm and helpful staff. Fantastic breakfast included! 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 18 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9/10 Wonderful! (441 reviews) Staff was really nice Reviewed on Mar 24, 2026 ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago Save 100% on your flight $955 per person Jun 4 - Jun 9 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (3,039 reviews) Clean but small rooms, nice location, the hotel offers bag holding service for a small fee so you don't have to lug em around the city. Reviewed on Mar 25, 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 $663 per person Jun 17 - Jun 20 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.8/10 Excellent! (1,894 reviews) Extremely clean hotel!!All staff was very friendly! Hotel was close to the St. Patrick’s Day parade; exactly why we came! Really enjoyed our stay!! Reviewed on Mar 25, 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/2026-04-25/2026-05-02/?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) ![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 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 $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 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 $225 nightly $264 total Apr 25 - Apr 26 Total with taxes and fees 8.4/10 Very Good! (2,241 reviews) Aside from the location for an overnight between flights & a great staff this hotel leaves a lot to be desired. Worn out carpets and fixtures and a climate system that is in need of an update. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F25%2F2026&endDate=4%2F26%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 $135 nightly $154 total Apr 6 - Apr 7 Total with taxes and fees 8.8/10 Excellent! (2,433 reviews) Dddd 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=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) It was all good! Reviewed on Mar 23, 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%2F26%2F2026&endDate=3%2F27%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 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