Highwood Vacation Packages

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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, Lake Forest College and Marriott Theatre. No matter your travel plans or the size of your budget, putting together a tailored Highwood vacation is a breeze with Expedia.

Top Highwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Hotel Riu Plaza Chicago
Aloft Chicago Downtown River North
Level Chicago - River North
The Emily Hotel

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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Highwood Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Mar 7 to Mar 8
CA $266
CA $312 total
Mar 7 - Mar 8
includes taxes & fees
8.2/10 Very Good! (2,215 reviews)
A very good value. A bit worn, great bed but half the price of the Westin Denver airport.

Reviewed on Feb 8, 2026

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Feb 27 to Feb 28
CA $194
CA $228 total
Feb 27 - Feb 28
includes taxes & fees
8.6/10 Excellent! (1,221 reviews)
All the staff were welcoming, happy and polite. The room was cleaned and well-maintained. Thanks to the help of front desk staff we were able to access Internet, however it is a bit unclear if there was complimentary Wi-Fi and a little tricky to join the network.

Reviewed on Feb 9, 2026

Marriott Chicago O'Hare
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd Rosemont IL
Fully refundable
The price is CA $160 per night from Feb 16 to Feb 17
CA $160
CA $183 total
Feb 16 - Feb 17
includes taxes & fees
8.6/10 Excellent! (2,731 reviews)
Very nice

Reviewed on Feb 6, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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.

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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.