Find hotels in Highwood, IL from $59

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Highwood hotels

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (10,061 reviews)
"Staff was very helpful getting us rides and directions for what we wanted."
United States
Richard
6 days ago
$116 nightly
The price is $137
Apr 26 - Apr 27
Total with taxes and fees
Congress Plaza Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,757 reviews)
"I am very happy to stay above hotel. The breakfast is excellent."
United States
Omar
1 day ago
$146 nightly
The price is $172
Apr 12 - Apr 13
Total with taxes and fees
Hotel Riu Plaza Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,071 reviews)
"Wonderful welcoming staff made this some place."
United States
Jessica
2 days ago
$119 nightly
The price is $140
Apr 26 - Apr 27
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5,814 reviews)
"The location is great. A great coffee shop across the street."
United States
Tiffany
6 days ago
$139 nightly
The price is $163
Apr 19 - Apr 20
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,484 reviews)
"Enjoyed the convenient location. No complaints about the room or breakfast or bar or restaurant."
United States
Pascal
7 days ago
$252 nightly
The price is $296
May 9 - May 10
Total with taxes and fees
Hyatt Regency Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,385 reviews)
"Well styled decor. Wonderful bistro on street level with super cute outdoor patio."
United States
Kseniya
3 days ago
$128 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
Eurostars Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,402 reviews)
"The beds were very comfortable."
United States
Alexandra
3 days ago
$128 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,717 reviews)
"I love the location. People always s friendly and allow pets."
United States
EDITH
1 day ago
$188 nightly
The price is $221
May 8 - May 9
Total with taxes and fees
Hilton Chicago

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,072 reviews)
"Great location, historic building, everything you need for a business or pleasure trip."
United States
Robert
5 days ago
$123 nightly
The price is $144
Apr 13 - Apr 14
Total with taxes and fees
River Hotel

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,363 reviews)
"Very nice furniture to sit comfortably."
United States
Alexandros
6 days ago
$196 nightly
The price is $230
Apr 30 - May 1
Total with taxes and fees
The Royal Sonesta Chicago Downtown

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,875 reviews)
"Great downtown location. Nice big clean rooms. Close enough to Michigan avenue shopping."
United States
Jane
6 days ago
$170 nightly
The price is $200
Apr 12 - Apr 13
Total with taxes and fees
L7 Chicago by LOTTE

Hyatt Regency Deerfield

Hyatt Regency Deerfield
4.0 star property
Deerfield
8.8 out of 10, Excellent, (1,001 reviews)
"Room was clean and staff was nice! Would stay here again."
United States
Michelle
1 day ago
$127 nightly
The price is $143
Apr 19 - Apr 20
Total with taxes and fees
Hyatt Regency Deerfield

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,636 reviews)
"My favorite hotel!!! Love the ambiance, food, views, and rooms!!"
United States
Cora
3 days ago
$247 nightly
The price is $291
Apr 12 - Apr 13
Total with taxes and fees
LondonHouse Chicago, Curio Collection by Hilton

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,171 reviews)
"Very live hotel, nice staff and clean."
United States
Genesis
3 days ago
$106 nightly
The price is $124
Apr 12 - Apr 13
Total with taxes and fees
Aloft Chicago Mag Mile

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,243 reviews)
"Really friendly staff. Beautiful view of the navy pier. Loved how comfortable my bed was."
United States
Andrea
6 days ago
$245 nightly
The price is $288
Apr 10 - Apr 11
Total with taxes and fees
Swissotel - Chicago

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,261 reviews)
"Close to many tourist attractions. The staff were very friendly."
United States
Claudia
1 day ago
$143 nightly
The price is $168
Apr 12 - Apr 13
Total with taxes and fees
citizenM Chicago Downtown

Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield
4.0 star property
Deerfield
8.8 out of 10, Excellent, (1,294 reviews)
"Inside was clean well taken care. It has a good restaurant."
United States
Keith
2 days ago
$132 nightly
The price is $150
Apr 25 - Apr 26
Total with taxes and fees
Embassy Suites by Hilton Chicago North Shore Deerfield

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2,609 reviews)
"Clean room. Friendly staff. Great location!"
United States
Byron
2 days ago
$125 nightly
The price is $147
Apr 9 - Apr 10
Total with taxes and fees
Hotel Felix River North/Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,835 reviews)
"Clean and staff was nice."
United States
Ruth
5 days ago
$128 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
Courtyard by Marriott Chicago Magnificent Mile

Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,761 reviews)
"I Loved everything about it 10 10."
United States
AnTonae
1 day ago
$136 nightly
The price is $160
Apr 16 - Apr 17
Total with taxes and fees
Hyatt Place Chicago/River North
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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Highwood

Trip time! Discover the local cuisine in Highwood.

Photo by Tara Jabbari
Open Photo by Tara Jabbari

Top Highwood Hotel Reviews

More cheap stays in Highwood

Hotels in Highwood with star-rating

Find out more about Highwood

Top reasons to visit Highwood

  • Outdoor Adventures: Highwood features beautiful parks, nature preserves, and scenic beaches perfect for family outings and relaxation.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment with engaging activities suitable for visitors of all ages.
  • Local Shopping: Explore unique shops and local malls offering a variety of retail therapy options.
  • Community Vibe: Experience the friendly locals and vibrant urban atmosphere that make Highwood special.
  • Diverse Accommodation: Stay in a range of pet-friendly and LGBTQIA welcoming hotels and motels for a comfortable visit.

Find great hotels near Highwood

Highwood, Illinois offers a variety of accommodation options, from comfortable hotels to cozy motels, catering to both leisure and business travelers. With many properties being pet-friendly and LGBTQIA welcoming, you can enjoy a pleasant stay in this charming area. Explore the best hotels in Highwood and find the perfect lodging to suit your needs, whether you're here for a weekend getaway or an extended vacation.

  • Motel 6 Prospect Heights, IL: A budget-friendly option with a guest rating of 8.2, Motel 6 Prospect Heights, IL is perfect for travelers looking for simplicity and convenience. Located 8 miles away from Highwood, this motel offers pet-friendly accommodations, allowing you to bring your furry friends along. With amenities such as free pet stays and a welcoming atmosphere, it caters to both families and solo travelers. Enjoy basic comfort at an economical price, making it an ideal choice for those who prioritize affordability without sacrificing accessibility.
  • Holiday Inn Chicago North-Evanston by IHG: This 3-star hotel boasts a guest rating of 8.6 and is situated 13 miles from Highwood, making it a fantastic option for business travelers. The Holiday Inn Chicago North-Evanston combines professional amenities with a warm ambiance. Featuring modern meeting spaces, high-speed internet, and a business center, it caters to corporate needs while also offering comfortable rooms for relaxation. Guests appreciate the on-site dining options and fitness center, ensuring a well-rounded stay that balances work and leisure.
  • Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts: A budget-friendly hotel located 14 miles from Highwood, the Red Roof Inn is another great choice for pet owners, welcoming dogs and cats with specific weight restrictions. With a focus on affordability, this property provides essential amenities in a comfortable setting, making it suitable for travelers on a budget. Guests appreciate the straightforward accommodations and convenient access to local attractions, ensuring a pleasant stay without breaking the bank.

Where to stay in Highwood

Highwood, Illinois, offers a delightful blend of outdoor activities and family-friendly atmospheres. Visitors can explore numerous parks and picnic areas, perfect for relaxing and enjoying nature. The city's urban vibe, combined with its friendly locals, creates a welcoming environment for all. Nearby neighborhoods provide additional charm, making Highwood an ideal base for discovering the region's rich scenery and experiences. Whether you're seeking romance or adventure, you'll find it all in and around Highwood.

  • Chicago: As a bustling metropolis, Chicago offers a vibrant urban experience that is hard to match. Located a short distance from Highwood, this city is famous for its stunning skyline, diverse neighborhoods, and rich cultural scene. Visitors flock to Chicago year-round, especially during the summer months when outdoor festivals, shopping, and entertainment abound. Must-visit attractions include historic theaters, sports stadiums, and expansive urban parks. Enjoy world-class dining and shopping experiences, and immerse yourself in the city's lively atmosphere.
  • Highland Park: Just 2 miles from Highwood, Highland Park is a charming city known for its family-friendly vibe and outdoor activities. Visitors come here to enjoy music concerts, theater performances, and educational experiences. The city features lovely urban parks and access to scenic lakes, making it perfect for those seeking a blend of relaxation and entertainment. With a welcoming community and various cultural events, Highland Park is an ideal destination for families looking to explore local attractions.
  • Deerfield: Only 3 miles from Highwood, Deerfield is a delightful city that attracts visitors with its combination of family-oriented activities and urban charm. Known for its shopping centers and malls, Deerfield is a haven for those looking to indulge in retail therapy. The area also boasts beautiful urban parks and sports facilities, providing plenty of opportunities for outdoor fun. With a friendly atmosphere and numerous local attractions, Deerfield is perfect for a leisurely day of exploration.

Things to do near Highwood

Highwood, Illinois, is perfect for outdoor family vacations, offering a blend of scenic beauty and engaging activities. Visitors can explore educational attractions, shop at local malls and centers, and enjoy a movie at the local theater. Whether you're spending a day in nature or indulging in some retail therapy, Highwood has something for everyone to enjoy.

Shopping

In Highwood, you can enjoy shopping at local boutiques and specialty shops along Waukegan Avenue. If you're up for a drive, visit Gurnee Mills, about 12 miles away, featuring a wide range of outlet stores and dining options for a full shopping experience.

Recreation

Chevy Chase Country Club, located 6 miles from Highwood, offers a luxurious atmosphere with golf, spa services, and fine dining. Similarly, Ravinia Green Country Club, just 4 miles away, boasts elegant amenities and wellness programs. For a more extensive experience, Bridges of Poplar Creek Country Club, 20 miles away, combines luxury with nature.

Adventure

Explore the scenic trails at the Skokie Lagoons, perfect for hiking, biking, or kayaking amid lush nature. For a thrill, check out the Highwood Recreation Center, offering various sports facilities and programs to keep you active and engaged during your visit.

Nightlife

Experience the vibrant nightlife in Highwood at The Wine Cellar, where you can savor fine wines and small plates. For a lively atmosphere, visit The Public House, featuring craft beers and live trivia nights, perfect for mingling with locals and enjoying a fun evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Highwood

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Highwood are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Highwood is Monday. The most expensive day to stay in Highwood is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool makes it easy to choose your budget, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to narrow your choices by hotel type—if you select the Eco-certified filter, you'll find a range of sustainable and environmentally-friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay in Highwood with your flights and activities when you book an Expedia package.

Find the best attractions near Highwood

Highwood, Illinois, is perfect for outdoor and family vacations, offering stunning scenery and a variety of attractions. Visitors can enjoy beautiful beaches, urban parks, and nature preserves that cater to those looking for a memorable beach experience or outdoor adventure. With its inviting atmosphere and diverse points of interest, Highwood promises a delightful getaway for travelers seeking relaxation and family fun.

  • Six Flags Great America: Experience thrilling rides and attractions at this premier theme park located 13 miles from Highwood. With entertainment options for the entire family, it's a perfect destination for adrenaline seekers and those looking for fun-filled family vibes.
  • Chicago Botanic Garden: Just 4 miles away, this beautiful botanical garden offers a serene escape with stunning outdoor landscapes. Perfect for romantic strolls or family outings, the garden showcases diverse plant collections and seasonal displays.
  • Rosewood Beach: Located 4 miles from Highwood, Rosewood Beach invites you to unwind with its picturesque shoreline. Enjoy the sun, sand, and refreshing lake vibes while soaking up the natural beauty of the area.

Best time to go to Highwood

The best time to visit Highwood can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Highwood falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Highwood falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly CloudySlightly LowSlightly Low
February25.9°F (-3.4°C)Light RainMostly CloudySlightly LowSlightly Low
March36.1°F (2.3°C)Light RainMostly CloudyAverageAverage
April44.8°F (7.1°C)Light RainMostly SunnySlightly HighAverage
May55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
June66.0°F (18.9°C)Light RainMostly SunnyAverageSlightly High
July72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
August72.3°F (22.4°C)Light RainMostly SunnyAverageAverage
September66.2°F (19.0°C)Light RainMostly SunnySlightly HighSlightly High
October54.0°F (12.2°C)Light RainMostly SunnyAverageSlightly High
November41.4°F (5.2°C)Light RainMostly SunnyAverageAverage
December32.0°F (0.0°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Highwood

Traveling to Highwood, Illinois, is convenient with access to three major airports. Chicago O'Hare International Airport (ORD) is 17 miles away and offers nearby hotels like the 4.5-star Loews Chicago O'Hare Hotel and the Hyatt Regency O'Hare Chicago, both just 2 miles from the airport. Milwaukee General Mitchell International Airport (MKE) is 51 miles from Highwood, with hotel options such as the 4.5-star Pfister Hotel and Potawatomi Hotel & Casino, each 6 miles away. Additionally, Chicago Midway International Airport (MDW) is located 29 miles from Highwood, boasting luxury stays like The Langham, Chicago, and Nobu Hotel Chicago, both around 8 to 9 miles from the airport.

Frequently asked questions

What is the best area to stay in Highwood?
The best area to stay in Highwood is the downtown district, particularly along Green Bay Road and Sheridan Road, as it offers the most conveniences for travelers.

This central area is Highwood's main commercial and social hub, characterized by its collection of restaurants, pubs, and local shops. You'll find a variety of dining options within easy walking distance, ranging from casual eateries to more upscale establishments. The metra station is also located downtown, providing convenient access to Chicago for day trips.

Couples looking for a relaxed getaway will appreciate the downtown area's concentration of culinary experiences and entertainment. Many of the local businesses offer unique menus and an inviting space, superb for an evening out. The area's walkability means you can easily explore without needing a car.

Solo travelers will also find downtown Highwood appealing due to its accessibility and the variety of independent businesses.
When is the best time to go to Highwood?
The best time to go to Highwood is typically during the warmer months, from late spring through early autumn, when the weather is pleasant for outdoor activities and local events are in full swing.

For those planning to enjoy Highwood's culinary scene and outdoor dining, the period from June to September is ideal. Many restaurants feature outdoor seating, and the downtown area often hosts food-centric festivals and events. This time of year is excellent for couples looking for enjoyable evenings out.

Families might find late spring (May) or early autumn (October) particularly appealing. The weather is usually comfortable for exploring nearby parks and the Lake Michigan shoreline without the peak summer crowds.
Where can I find the best nightlife in Highwood?
Highwood's nightlife is primarily centered around its downtown area, offering a mix of casual spots and restaurants that extend their hours.

Green Bay Road, particularly the stretch between Washington Street and North Avenue, is where you'll find most of Highwood's evening establishments. This area hosts a collection of bars and restaurants, many of which feature regular live music, often jazz or blues, on weekends. You'll also find some establishments known for their wine lists or craft beer selections.

Another area to consider is Sheridan Road, specifically around the intersection of Highwood Avenue. While not as concentrated as Green Bay Road, this street has a few long-standing taverns and restaurants that offer a relaxed setting for evening drinks.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Highwood.
How can I save on a Highwood hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Highwood hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Highwood hotel?
Prices for hotels in Highwood often vary, but you can find a great deal from $59 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia