Highwood, IL

Travel Guide

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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
$212 nightly
The price is $249 total per night from Oct 17 to Oct 18
$249 total
Oct 17 - Oct 18
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.6/10 Excellent! (2,545 reviews)
"Very convenient to just walk to your hotel from the airport. Comfortable room. Excellent Fitness facility. I really liked it except for the price! $$$$"

Reviewed on Oct 11, 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
$161 nightly
The price is $189 total per night from Oct 30 to Oct 31
$189 total
Oct 30 - Oct 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
Marriott Chicago O'Hare
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$161 nightly
The price is $183 total per night from Oct 23 to Oct 24
$183 total
Oct 23 - Oct 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
9/10 Wonderful! (3,254 reviews)
"Close to O Hare airport and has convenient garage parking. Staff pleasant. Room clean. Bathroom very small. Restaurant/bar was open late for food & drinks which was nice for our late arrival"

Reviewed on Oct 11, 2026

Hyatt Regency O'Hare Chicago
See all 1,405 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.
The Gem Museum Suites

The Gem Museum Suites

3.5 out of 5
1555 Oak Avenue Evanston IL
Book a stay at this business-friendly aparthotel in Evanston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ryan Field and Baha'i House ...
9.4/10 Exceptional! (285 reviews)
"Loved having a cooked to order breakfast and a safe parking spot included. The hotel also had interesting clocks, stained glass and a large lobby area. Good local resturants in easy walking distance from the hotel."

Reviewed on Oct 11, 2026

The Gem Museum Suites
Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Chicago IL
Stay at this vacation home in Chicago. Enjoy a pool table, an in-room coffeemaker, and air conditioning. Popular attractions Wrigley Field and Portage Park are ...
10/10 Exceptional! (9 reviews)
"Worked well for family visit thanks!"

Reviewed on Sep 14, 2026

Sleeps 18 • 8BR • Game Room • Gym • Theater
King Bed Non-Smoking

King Bed Non-Smoking

Chicago IL
Stay at this apartment in Des Plaines. Enjoy cable/satellite TV service and air conditioning. Popular attractions Allstate Arena and Camp Pine Woods are located ...
10/10 Exceptional! (288 reviews)
Room was on the smaller side but had everything needed for work. WiFi was reliab ...
"Room was on the smaller side but had everything needed for work. WiFi was reliable and fast, which helped me get my tasks done without interruption. Housekeeping was attentive too, keeping the space tidy each day."

Reviewed on Jun 12, 2026

King Bed Non-Smoking
See all 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
LEGOLAND® Discovery Center Chicago

LEGOLAND® Discovery Center Chicago

$26
per adult
92% of travellers recommend
LEGOLAND® Discovery Center Chicago
Museum of Illusions Chicago Admission Ticket

Museum of Illusions Chicago Admission Ticket

$43
per adult
Museum of Illusions Chicago Admission Ticket
Spirit of Chicago Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

$74
per adult
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan
See all activities in Highwood

Frequently asked questions

Is Highwood worth visiting?
Highwood is worth visiting for its food and local dining, offering delicious Italian and European cuisine. Travelers also benefit from practical transit access, with convenient train services making it easy to explore the area and enjoy its culinary offerings.
When is the best time to visit Highwood?
The best time to visit Highwood is from May through September, when the weather is generally pleasant for exploring. For fewer crowds and better value, the quieter months of December through March are a good option, offering a different experience during the cooler winter season.
How do you get around Highwood?
Highwood offers train service, providing a convenient way for travelers to get around. Stations such as Highwood Station and Highland Park Fort Sheridan Station connect you to various parts of the area, making local travel straightforward.
What cuisines can you find in Highwood?
In Highwood, travelers can find Mediterranean cuisine, offering dishes such as hummus, falafel, gyros, and kebabs. You'll also discover Italian favorites like pasta and pizza, alongside North American, Asian, and Latin American options.
Can I book a refundable hotel in Highwood?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Highwood by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Highwood with Expedia?
Expedia makes it easier to plan your Highwood trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Highwood?
The best choice depends on your travel style. Hotels in Highwood can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Highwood trip on Expedia?
Once you've booked your Highwood trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Highwood trip?
Expedia offers customer support before, during, and after your Highwood trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Highwood?
If it's your first trip to Highwood, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Highwood hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Highwood hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Highwood

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Highland Park

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Lake Forest

A city skyline with modern skyscrapers and a river with boats and people in the foreground.

Chicago

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