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Our top choices for Highwood hotels

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2,615 reviews)
"The room was clean and the staff was very friendly."
United States
Andrea
$164 nightly
The price is $192
Feb 21 - Feb 22
Total with taxes and fees
Hilton Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,470 reviews)
"Clean room, great staff, great location "
United States
Tiffany
$201 nightly
The price is $236
Feb 22 - Feb 23
Total with taxes and fees
Hyatt Regency Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,796 reviews)
"Great stay"
United States
Jennifer
$90 nightly
The price is $106
Feb 17 - Feb 18
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,371 reviews)
"Great stay"
United States
Blake
$151 nightly
The price is $178
Feb 17 - Feb 18
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,301 reviews)
"Awesome quite hotel beds are amazing great location "
United States
jamie
$92 nightly
The price is $108
Feb 16 - Feb 17
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,321 reviews)
"Everything was on point… we love the location"
United States
Beryl Ivonne
$171 nightly
The price is $201
Feb 20 - Feb 21
Total with taxes and fees
The Royal Sonesta Chicago Downtown

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,230 reviews)
"Nice location, friendly staff and room was nice"
United States
DeAshley
$96 nightly
The price is $113
Feb 22 - Feb 23
Total with taxes and fees
Eurostars Magnificent Mile

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,000 reviews)
"Great stay, good location, accommodating staff."
United States
Ian
$86 nightly
The price is $101
Feb 26 - Feb 27
Total with taxes and fees
River Hotel

Hyatt Regency Deerfield

Hyatt Regency Deerfield
4.0 star property
Deerfield
8.6 out of 10, Excellent, (1,004 reviews)
"nice large room with updated decor, gorgeous bath with super White, clean, fresh towels and linens on the bed!"
United States
Deborah
$110 nightly
The price is $124
Feb 26 - Feb 27
Total with taxes and fees
Hyatt Regency Deerfield

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, (5,655 reviews)
"Always a great stay, clean, great breakfast, great pool. "
United States
Zachary
$103 nightly
The price is $120
Feb 22 - Feb 23
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,601 reviews)
"Staff was friendly and loved the decor at this hotel…will definitely be staying again"
Canada
Osama
$163 nightly
The price is $192
Feb 22 - Feb 23
Total with taxes and fees
LondonHouse Chicago, Curio Collection by Hilton

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,637 reviews)
"Great location and overall great hotel."
United States
Fernando
$157 nightly
The price is $184
Feb 11 - Feb 12
Total with taxes and fees
L7 Chicago by LOTTE

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, (1,280 reviews)
"Great hotel "
United States
Novella
$107 nightly
The price is $122
Feb 21 - Feb 22
Total with taxes and fees
Embassy Suites by Hilton Chicago North Shore Deerfield

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,083 reviews)
"Great place"
United States
Nicholas
$89 nightly
The price is $105
Mar 8 - Mar 9
Total with taxes and fees
Club Quarters Hotel Wacker at Michigan, Chicago

Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,694 reviews)
"Great stay "
United States
Amparo
$117 nightly
The price is $137
Feb 17 - Feb 18
Total with taxes and fees
Hyatt Place Chicago/River North

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,807 reviews)
"Amazing place to stay"
United States
victor
$188 nightly
The price is $221
Feb 22 - Feb 23
Total with taxes and fees
InterContinental Chicago Magnificent Mile by IHG

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,187 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
$144 nightly
The price is $170
Feb 15 - Feb 16
Total with taxes and fees
Swissotel - Chicago

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, (2,552 reviews)
"I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic."
United States
Equilla
$95 nightly
The price is $111
Feb 22 - Feb 23
Total with taxes and fees
Hotel Felix River North/Magnificent Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,318 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
$137 nightly
The price is $161
Feb 11 - Feb 12
Total with taxes and fees
Hotel Riu Plaza Chicago

Courtyard by Marriott Chicago Highland Park/Northbrook

Courtyard by Marriott Chicago Highland Park/Northbrook
3.0 star property
Highland Park
9.0 out of 10, Wonderful, (1,000 reviews)
"Good location"
United States
Peter
$107 nightly
The price is $119
Feb 20 - Feb 21
Total with taxes and fees
Courtyard by Marriott Chicago Highland Park/Northbrook
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Learn more about Highwood

Trip time! Discover the local cuisine in Highwood.

The most delicious cookies I have ever had, I'm sure you will agree!!
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 offers scenic views and local beaches, perfect for relaxation and exploration.
  • Live Music and Events: Enjoy vibrant live music concerts that enhance the lively atmosphere of the area.
  • Family-Friendly Activities: The area is ideal for families, featuring parks and recreational spaces for all ages.
  • Charming Neighborhoods: Stroll through friendly streets lined with unique shops and eateries.
  • Diverse Accommodations: A variety of hotels cater to different traveler needs, ensuring a comfortable stay.

Find great hotels near Highwood

Discover a variety of hotel accommodations in Highwood, Illinois, designed to meet the diverse needs of travelers. Whether you're seeking a business-friendly environment, a pet-friendly stay, or an LGBTQIA welcoming experience, Highwood offers an array of options. With competitive hotel prices and convenient locations, you can enjoy a comfortable retreat while exploring this charming area. Find your perfect stay in Highwood, where hospitality meets modern amenities.

  • Holiday Inn Chicago North-Evanston by IHG: Experience a perfect blend of business and leisure at the Holiday Inn Chicago North-Evanston by IHG. Located 13 miles from Highwood, this 3-star hotel is ideal for business travelers seeking a welcoming atmosphere. The property proudly supports LGBTQIA travelers and offers a variety of amenities tailored to meet business needs, including multiple meeting rooms, accessible business center, and versatile conference space. Guests appreciate the modern comfort of the rooms, alongside the convenience of on-site dining options.
  • Motel 6 Prospect Heights, IL: A budget-friendly option just 8 miles from Highwood, Motel 6 Prospect Heights, IL offers a welcoming environment for pet owners. This motel is perfect for travelers who want to bring their furry friends along, as it features a pet-friendly policy that allows pets on-site without additional fees for service animals. Guests enjoy the straightforward accommodations and the convenience of being near local attractions, making it an excellent choice for those in need of a comfortable, no-frills stay.
  • DoubleTree by Hilton Chicago - North Shore Conference Center: Just 11 miles from Highwood, the DoubleTree by Hilton Chicago - North Shore Conference Center is a luxurious 4-star hotel that caters to families, shoppers, and LGBTQIA travelers alike. The property is situated in a vibrant shopping district, offering easy access to popular retail destinations. Families will appreciate the thoughtful amenities, including complimentary cribs for little ones. Guests are welcomed with a signature chocolate chip cookie upon arrival, setting the tone for a delightful stay filled with comfort and convenience.

Where to stay in Highwood

Highwood, Illinois, offers a delightful blend of outdoor activities and family-friendly vibes, making it an ideal vacation spot. Explore the charming streets lined with friendly faces, and enjoy stylish getaways in nearby neighborhoods. Take advantage of the lush parks for a scenic retreat or engage in the vibrant local culture. With its perfect mix of urban charm and serene landscapes, Highwood promises a memorable experience for both relaxation and adventure.

  • Chicago: As a bustling metropolis, Chicago is a must-visit destination filled with rich culture and vibrant life. Located a short distance from Highwood, the city attracts visitors year-round, with peak travel during the summer months. Families and outdoor enthusiasts flock to Chicago for its extensive shopping areas, arena entertainment, and educational attractions. Notable landmarks such as the iconic stadiums and tourist precincts offer unforgettable experiences, making it a hub for city-themed adventures.
  • Highland Park: Just 2 miles from Highwood, Highland Park is a charming city known for its family-friendly atmosphere and outdoor activities. Visitors enjoy a steady flow of tourism, especially from May to July. The city is home to a variety of music concerts, theaters, and educational venues, ensuring that there’s always something happening. Its local attractions, including beautiful urban parks and scenic beaches by the lake, provide perfect spots for relaxation and recreation.
  • Deerfield: Located 3 miles away from Highwood, Deerfield is a vibrant city that attracts visitors for its family-oriented and outdoor experiences. With travel peaks in April and the summer months, this city offers a mix of educational opportunities, music concerts, and shopping areas. Key local landmarks include stadiums and urban parks, which make it an ideal location for both leisurely strolls and energetic activities. Deerfield ensures a delightful experience for all types of travelers.

Things to do near Highwood

Highwood, Illinois, is perfect for outdoor family vacations with its scenic views and vibrant atmosphere. Visitors can enjoy a variety of activities, including relaxing at the lazy river and attending live music concerts. The area also features educational opportunities and recreational spaces, making it an ideal destination for those seeking entertainment and relaxation. Experience the charm of Highwood and create lasting memories with your loved ones.

Shopping

In Highwood, you can enjoy local shopping at unique boutiques and specialty stores. If you're up for a drive, visit Gurnee Mills for a larger shopping experience with entertainment options, or explore Schaefer's Wines and Liquors and Wolff's Flea Market for local finds.

Recreation

Experience live music at Ravinia Pavilion, where the vibrant atmosphere enhances your enjoyment of concerts. For an active day, head to Highland Park Country Club for a round of golf surrounded by beautiful landscapes. Finally, indulge in the luxury of Chevy Chase Country Club, offering a serene retreat.

Adventure

Experience the thrilling Great Wolf Lodge Water Park, located 14 miles from Highwood, featuring exciting slides and family-friendly activities. For water sports enthusiasts, Jet Funn offers adrenaline-pumping adventures 23 miles away. In winter, hit the slopes at Wilmot Mountain, a ski field 28 miles from Highwood for skiing and snowboarding fun.

Nightlife

Experience the vibrant nightlife in Highwood by visiting the Citadel Theatre Company for a cultural night filled with romance and entertainment. For a fun adventure, head to Xtreme Trampolines, where you can enjoy an exciting arcade atmosphere. Don’t miss the Marriott Theatre for an unforgettable performance.

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

Booking tips and Expedia advantages for Highwood

To save money on your trip to Highwood, plan your visit between December and February when hotel prices are lower. Wednesdays are the cheapest days to stay, while Saturdays tend to be the most expensive. Use Expedia to find budget-friendly accommodations by sorting options from lowest to highest price, and consider booking a package deal to save on hotels, flights, and activities. Joining Expedia's One Key membership can also provide exclusive discounts and earn you OneKeyCash for future stays. Don't forget to search for flash sales and savvy savings for great value.

  • 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 Wednesday. The most expensive day to stay in Highwood is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your options based on your budget, preferred location, and desired hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Highwood hotel reservation with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Highwood

Highwood, Illinois, is perfect for outdoor enthusiasts and families seeking scenic adventures. Visitors can enjoy local beaches and urban parks, making it an ideal spot for relaxation and exploration. The area also features modern colleges and universities, adding a vibrant atmosphere. Whether you're looking for an urban experience or a family outing, Highwood has a variety of attractions to suit every traveler's interests.

  • Six Flags Great America: Located 13 miles away from Highwood, this thrilling theme park offers a variety of rides and attractions for all ages. From adrenaline-pumping roller coasters to family-friendly entertainment, it’s the perfect spot for a day full of fun and excitement.
  • Northwestern University: Also 13 miles from Highwood, this prestigious university features stunning architecture and a vibrant campus atmosphere. Stroll through the grounds to appreciate its modern design and lively city vibes, making it a great cultural stop.
  • Chicago Botanic Garden: Just 4 miles from Highwood, this beautiful botanical garden is an oasis of tranquility. With lush landscapes and romantic settings, it’s ideal for families or couples looking to enjoy nature and peaceful outdoor strolls.

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

Visiting Highwood, Illinois, is convenient with several major airports nearby. Chicago O'Hare International Airport (ORD) is 17 miles away, offering 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's General Mitchell International Airport (MKE) is 51 miles away, with excellent options such as The Pfister Hotel and Potawatomi Hotel & Casino, both 6 miles from MKE. Chicago Midway International Airport (MDW) is located 29 miles away, with luxury hotels like Trump International Hotel & Tower and Nobu Hotel Chicago, situated 8 to 10 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 $43 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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