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

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,198, price is now CA $701 per person
CA $701
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on Feb 9, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,555, price is now CA $1,033 per person
CA $1,033
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Friendly staff, tasteful room

Reviewed on Feb 11, 2026

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was CA $1,214, price is now CA $872 per person
CA $872
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Staff was great but next to fire station. Beware very noisy if staying city view

Reviewed on Feb 8, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,154, price is now CA $837 per person
CA $837
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.

Reviewed on Jan 19, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,560, price is now CA $1,140 per person
CA $1,140
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Amazing hotel. Always stay here when I make a trip to Chicago.

Reviewed on Feb 10, 2026

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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
See all 1,464 properties in Highwood
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.
All Inclusive Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Highwood

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

Michigan Avenue

4.5/5(19 reviews)

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.

Michigan Avenue
Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Millennium Park featuring autumn colours, street scenes and a city

Millennium Park

4.5/5(722 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Highwood

Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Highwood

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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.