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Our top choices for Highwood hotels

1. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (10,205 reviews)
"The room was clean. All the staff was very friendly."
United States
Todd
1 day ago
$145 nightly
The price is $172
Aug 30 - Aug 31
Total with taxes and fees
Congress Plaza Hotel

2. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,925 reviews)
"Very clean rooms. Overall extremely enjoyable. Location was perfect."
United States
Seth
1 day ago
$222 nightly
The price is $264
Aug 30 - Aug 31
Total with taxes and fees
Hotel Riu Plaza Chicago

3. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (1,916 reviews)
"Great experience staff was really helpful."
United States
Dante
1 day ago
$152 nightly
The price is $181
Aug 23 - Aug 24
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast

4. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,732 reviews)
"Great location, rooms very comfortable and with a great size."
United States
CHRISTIAN GIOVANNI
1 day ago
$161 nightly
The price is $191
Aug 30 - Aug 31
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites

5. Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,970 reviews)
"Omni is always a great stay. Wonderful, large room and grrat service."
United States
Monika
1 day ago
$251 nightly
The price is $298
Aug 9 - Aug 10
Total with taxes and fees
Omni Chicago Hotel

6. Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
4.0 star property
Rosemont
8.8 out of 10, Excellent, (2,951 reviews)
"The staff was super friendly."
United States
Mary
3 days ago
$169 nightly
The price is $193
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Regency O'Hare Chicago

7. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,886 reviews)
"Rooms were well maintained. Very helpful at check. Especially Ken was welcoming."
United States
Mariya
1 day ago
$152 nightly
The price is $181
Aug 23 - Aug 24
Total with taxes and fees
The Chicago Hotel Collection - Magnificent Mile

8. River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,400 reviews)
"Location was great! Good size room. Staff were super friendly."
United States
Derek
1 day ago
$160 nightly
The price is $190
Aug 31 - Sep 1
Total with taxes and fees
River Hotel

9. Hyatt Regency Deerfield

Hyatt Regency Deerfield
4.0 star property
Deerfield
8.8 out of 10, Excellent, (1,113 reviews)
"Pro Room for as very spacious and clean."
United States
Cyndi
3 days ago
$127 nightly
The price is $143
Aug 21 - Aug 22
Total with taxes and fees
Hyatt Regency Deerfield

10. Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield
4.0 star property
Deerfield
9.0 out of 10, Wonderful, (1,344 reviews)
"I appreciated the on site restaurant and quality of the accommodations."
United States
Robert and Camie
8 days ago
$133 nightly
The price is $151
Aug 16 - Aug 17
Total with taxes and fees
Embassy Suites by Hilton Chicago North Shore Deerfield

11. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,780 reviews)
"Beautiful hotel, loved the concrete ceilings, honestly, Staff super helpful and polite would stay again."
United States
Dmitrius
1 day ago
$196 nightly
The price is $233
Aug 17 - Aug 18
Total with taxes and fees
Eurostars Magnificent Mile

12. The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,728 reviews)
"Great water pressure. Perfect location for dining."
United States
Thomas
3 days ago
$222 nightly
The price is $264
Aug 30 - Aug 31
Total with taxes and fees
The Allegro Royal Sonesta Hotel Chicago Loop

13. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,336 reviews)
"I would highly recommend CitizenM Chicago to anyone visiting the city."
United States
Martin
1 day ago
$179 nightly
The price is $213
Aug 30 - Aug 31
Total with taxes and fees
citizenM Chicago Downtown

14. Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (3,261 reviews)
"Very close to all the attractions. Parking is nearby. Staff are OK."
Canada
Salvador
5 days ago
$117 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Freehand Chicago

15. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,504 reviews)
"Nice size rooms. Fantastic downtown river location. What an awesome boutique hotel."
United States
Tom
1 day ago
$189 nightly
The price is $225
Aug 9 - Aug 10
Total with taxes and fees
L7 Chicago by LOTTE

16. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,558 reviews)
"Great customer service. One of the best Hotels I've stayed."
United States
Gregory
1 day ago
$211 nightly
The price is $251
Sep 2 - Sep 3
Total with taxes and fees
The Royal Sonesta Chicago Downtown

17. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,609 reviews)
"Staff for the most part were friendly. A mini fridge in the room."
United States
Robin
1 day ago
$143 nightly
The price is $170
Aug 30 - Aug 31
Total with taxes and fees
Club Quarters Hotel, Central Loop, Chicago

18. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,184 reviews)
"Making it perfect for exploring Chicago."
United States
Ivana
8 days ago
$274 nightly
The price is $326
Sep 2 - Sep 3
Total with taxes and fees
InterContinental Chicago Magnificent Mile by IHG

19. 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, (5,997 reviews)
"Great location and friendly staff. Clean with amenities."
United States
Phillip
1 day ago
$162 nightly
The price is $221
Sep 1 - Sep 2
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North

20. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,811 reviews)
"This hotel was absolutely beautiful. The rooms were very nice."
United States
Shameika D
2 days ago
$232 nightly
The price is $276
Aug 30 - Aug 31
Total with taxes and fees
LondonHouse Chicago, Curio Collection by Hilton
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Where to stay in Highwood

Highwood offers a delightful blend of outdoor adventures and family-friendly activities. Explore nearby beach destinations, soak up the sun during the warm summers in Highwood, and immerse yourself in the vibrant culture of the area. Don't miss the charming atmosphere of nearby neighborhoods like Illinoiswood Dale for a complete experience.

Chicago

Chicago is the ultimate metropolis for travelers looking for a vibrant cultural experience. Those visiting will appreciate the bustling shopping along Michigan Avenue, the excitement of events at McCormick Place, and the fun at Navy Pier. Situated in Chicago, Highwood offers easy access to these attractions, making it a smart choice for your stay. With a variety of activities year-round, Chicago is an ideal spot for a memorable vacation.

Highland Park

Experience the charm of Highland Park, an excellent hub for travelers eager to explore the vibrant attractions of the area. Just a short drive away from Highwood, this city offers access to stunning sites like the Chicago Botanic Garden, Northwestern University, and Six Flags Great America. With a mix of outdoor adventures and entertainment options, Highland Park provides a delightful stay year-round, making it a smart choice for your vacation.

Deerfield

Families and weekend getaway travelers will love Deerfield, known for its vibrant blend of outdoor activities and urban experiences. With attractions like Northwestern University, the beautiful Chicago Botanic Garden, and the thrilling Six Flags Great America, there’s something for everyone to enjoy. Located about 3 miles from Highwood, Deerfield offers easy access to a variety of shopping centers and parks, making it a smart choice for your stay in the area.

Bannockburn

Immerse yourself in Bannockburn, a neighborhood perfect for travelers seeking a blend of business, family fun, and weekend getaways. This area offers easy access to attractions like the thrilling Six Flags Great America, the serene Chicago Botanic Garden, and the educational environment of Northwestern University. Just about 3 miles from Highwood, Bannockburn provides a smart choice for your stay, allowing you to enjoy both urban experiences and relaxing escapes.

Lake Forest

Travelers visiting the area often choose Lake Forest, especially families and leisure seekers looking for a vibrant escape. This charming city offers access to popular attractions like Six Flags Great America for thrilling adventures, Rosalind Franklin University for educational experiences, and the serene Chicago Botanic Garden for nature lovers. Located about 4 miles by car from Highwood, Lake Forest provides a seamless transition between urban excitement and tranquil outdoor spaces, making it a smart choice for your stay.

Stay near popular attractions around Highwood

Nestled in the heart of Illinois, Highwood offers a delightful blend of outdoor adventures and family-friendly activities. Explore scenic parks, relax at nearby beaches, and indulge in shopping at Woodfield Mall. Don’t miss the vibrant atmosphere of Highland Park, perfect for creating lasting memories.

Learn more about Highwood

Trip time! Discover the local cuisine in Highwood.

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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 much is the nightly rate at a Highwood hotel?
Prices for hotels in Highwood often vary, but you can find a great deal from $62 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.

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