Highwood Holidays from £1,475
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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
Swissotel - Chicago
Reviewed on 26 May 2026
Level Chicago Fulton Market
Reviewed on 22 May 2026
theWit Chicago, a Hilton Hotel
Reviewed on 27 May 2026
Trump International Hotel & Tower Chicago
Reviewed on 27 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on 26 May 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
Hyatt Regency O'Hare Chicago
"I’ve stayed at the hotel about 20 years ago. And was surprised at how run down it was. However floors 3 and 4 were shut down and being renovated. Assume that the entire hotel is being renovated. Check-in staff was very helpful. And gave me extended check out for the next day. But the next day staff ..."
Reviewed on 27 May 2026
Hilton Chicago O'Hare Airport
"Very convenient to airport for late arrival after overseas flight and for early departure without need for train or cab etc. would recommend highly for this reason and will use again. Room was clean, cool, and quiet."
Reviewed on 26 May 2026
Holiday Inn Chicago O'Hare – Rosemont by IHG
"Great place, very clean and organized. Nice pool & exercise area. The restaurant was very short staffed and backed up… not a big deal. The food was fantastic!"
Reviewed on 26 May 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
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* 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.
