Highwood Holidays from £670
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Your Highwood Holiday
Book a custom holiday package to Highwood and get ready to experience this incredible city how you like. Consider staying in the neighbourhood 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, Lake Forest College and Marriott Theatre. No matter your travel plans or the size of your budget, putting together a tailored Highwood holiday is a breeze with Expedia.
Top Highwood Flight + Hotel Deals
Waldorf Astoria Chicago
Reviewed on 26 Jan 2026
Level Chicago Fulton Market
Reviewed on 16 Feb 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Reviewed on 25 Feb 2026
Highwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 5,400 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Genesee Theatre, Marriott Theatre and Kohl Childrens Museum |
Top hotels in Highwood
Holiday Inn Chicago North-Evanston by IHG
The room was very dated. There were no extra amenities such as f stops, hair cover, etc. The shower curtain was too short, resulting in the floor getting soaked. The staff neglected to make up our room one day and when we complained we got the runaround saying it must have been our fault that we ...
Reviewed on 25 Feb 2026
Hilton Chicago O'Hare Airport
Food was great at the Aviator. The room was clean, quiet and comfortable and everyone went out of their way at the front desk to accommodate us.
Reviewed on 26 Feb 2026
Hyatt Regency O'Hare Chicago
Great experience
Reviewed on 26 Feb 2026
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highwood
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour
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. Flight-inclusive packages are ATOL protected.
