Highland Park(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Highland Park, Illinois, the top choice for families is Hyatt House Chicago North Shore, located just minutes from Lake Michigan and downtown. This hotel offers spacious family rooms, complimentary breakfast, and a dedicated kids' play area. Its safe, tree-lined neighborhood is close to Highland Park Public Library, Parks, and Chicago’s North Shore schools, making it ideal for parents seeking both convenience and tranquility. Guests can easily access Chicago’s Loop via Metra trains or car (30 minutes), perfect for day trips to Millennium Park or Navy Pier. The surrounding community also hosts seasonal events like outdoor concerts and farmers' markets, adding cultural depth to your stay.

Additionally, Highland Park's low crime rate and strong emphasis on education create a secure, enriching environment—ideal for raising children or traveling with them. With its blend of suburban comfort and urban accessibility, this hotel delivers a seamless experience for families exploring the greater Chicago area.

For the quietest hotel experience in Highland Park, choose accommodations near the Lakefront Residential District along Lake Michigan. This area features historic Victorian homes, lush greenery, and tranquil streets with minimal traffic. Stay at The Carriage House Inn, a boutique bed & breakfast nestled in a 19th-century estate, offering private gardens, reading nooks, and a serene atmosphere perfect for solo travelers or couples seeking relaxation. The location is just a 5-minute walk from Highland Park Library and local cafes, allowing easy access to amenities without sacrificing peace. With excellent lighting, clean sidewalks, and high safety standards, this district balances privacy with accessibility. It’s also an ideal base for exploring Chicago’s North Shore while enjoying a slower, more intimate pace of life away from city crowds.

Visitors to Highland Park can immerse themselves in its rich heritage through several distinctive cultural experiences. Attend the annual Lakeside Summer Festival, featuring live music, craft fairs, and family picnics held in Highland Park Park, which reflects the town’s strong community spirit. Explore the Highland Park Historical Society Museum, housed in a restored 1903 Carnegie-funded library, showcasing artifacts from the town’s early days as a Chicago elite retreat. For educational enthusiasts, visit the University of Chicago Laboratory Schools campus—a pioneering site of progressive education founded by John Dewey. These experiences highlight Highland Park’s legacy as one of the first planned communities in the Midwest, blending civic pride, academic excellence, and a deep appreciation for public space.

Moreover, the town’s architecture, parks, and annual events reflect a commitment to thoughtful urban design and cultural continuity, offering travelers a rare glimpse into authentic American small-town values.

Yes, Highland Park offers several quiet, welcoming hotels ideal for solo travelers. The Carriage House Inn stands out as a boutique retreat set in a preserved 19th-century home, providing private suites with cozy reading corners, free Wi-Fi, and 24-hour front desk service. Located in a safe, residential zone near Highland Park Library and local cafés, it fosters a sense of connection without noise or disruption. The inn hosts small gatherings and book clubs, encouraging meaningful interactions with fellow guests. Its proximity to Lake Michigan and scenic walking trails makes it perfect for those seeking solitude and nature. With minimal foot traffic and well-lit streets, the area ensures security and comfort. Whether you're working remotely or exploring the North Shore, this hotel blends privacy, charm, and hospitality—perfect for independent travelers who value authenticity and calm.

Highland Park is highly accessible to downtown Chicago. The Hillside Metra Station provides direct train service to Chicago Union Station in just 30 minutes, with frequent departures throughout the day. Major hotels like Hyatt House Chicago North Shore offer shuttle services to O’Hare International Airport and downtown locations. Alternatively, driving via I-90/I-94 takes approximately 30 minutes to reach Millennium Park or Michigan Avenue. The town’s strategic position in the North Shore suburbs places it within easy reach of major business hubs, universities, and cultural venues. This balance of suburban serenity and urban connectivity makes Highland Park an ideal base for business travelers, tourists, and commuters alike—offering the best of both worlds: quiet living and instant access to the heart of Chicago.

Key historical landmarks in Highland Park include the Highland Park Municipal Building (1890), a striking example of Gothic Revival architecture with intricate stonework and a prominent clock tower. The Highland Park Public Library, established in 1903 with funding from Andrew Carnegie, is a designated historic site and now serves as a cultural center. The Highland Park Cemetery holds graves of early civic leaders and educators, reflecting the town’s founding elite. Another notable site is the original campus of the University of Chicago Laboratory Schools, where John Dewey developed his progressive education model. These sites collectively illustrate Highland Park’s role as one of the earliest planned communities in the Midwest, shaped by intellectualism, civic pride, and architectural integrity. Guided tours and self-guided maps are available through the local historical society for deeper exploration.

Visitors to Highland Park should sample The Maple Tree Café’s house-made pancakes with locally sourced honey and organic yogurt, a staple of the town’s farm-to-table ethos. At Hillside Bistro, try their signature grilled lake trout with herb-infused potatoes—an homage to Lake Michigan’s natural bounty. During weekends, explore the Highland Park Farmers Market, where vendors sell artisanal ice cream, sourdough bread, and craft beer from nearby microbreweries. Many restaurants feature vintage décor—wood beams, brass fixtures, and antique mirrors—creating a warm, nostalgic ambiance. What sets Highland Park apart is its focus on community-driven cuisine: meals are often shared over conversations, fostering connections between locals and travelers. These dining experiences reflect the town’s values—quality, sustainability, and human-centered hospitality.

Absolutely. Highland Park is a prime destination for business travelers. The Hyatt House Chicago North Shore features modern meeting rooms, high-speed internet, and a business center equipped for virtual conferences. Its proximity to Chicago’s Loop—just 30 minutes by train or car—makes it ideal for attending meetings at Michigan Avenue or Navy Pier. The area hosts numerous corporate offices, research centers, and institutions linked to Northwestern University and the University of Chicago, creating a professional network. Hotels provide concierge services, luggage storage, and express check-out, streamlining travel logistics. With reliable transportation links to O’Hare and Midway Airports, and a reputation for safety and efficiency, Highland Park offers a productive yet peaceful environment—perfect for executives, consultants, and remote workers seeking a balanced, high-performance stay.

Highland Park boasts several scenic paths perfect for walking and biking. The Lakefront Trail runs along Lake Michigan for about 3 kilometers, offering panoramic views, shaded benches, and opportunities to spot migratory birds. The trail is well-maintained with clear signage and nighttime lighting, ensuring safety. Another favorite is the Highland Park Park Greenway, a multi-use path connecting parks, playgrounds, and community centers, ideal for family rides or morning jogs. It uses eco-friendly asphalt and includes dedicated bike lanes. For nature lovers, the Highland Park Riverwalk Preserve offers a quieter loop through wetlands and native plants, with interpretive signs explaining local ecology. All trails are patrolled regularly, have emergency call stations, and are dog-friendly. Visit during early morning or late afternoon to avoid heat and enjoy the crisp lake breeze—perfect for rejuvenating walks or peaceful cycling.

Don’t miss the Lakeside Summer Festival in July—a three-day celebration featuring live music, food trucks, craft booths, and outdoor film screenings in Highland Park Park. It embodies the town’s vibrant community spirit. In autumn, attend the Pumpkin Light Festival, where residents carve jack-o’-lanterns and participate in a glowing parade through the park, followed by storytelling and bonfires. The Spring Garden Open House invites visitors into private gardens and historic homes, showcasing meticulously maintained rose beds and English-style lawns—a tribute to Highland Park’s love of horticulture. These events, rooted in tradition and neighborly connection, reflect the town’s identity as a place where culture, nature, and community thrive. They’re ideal for travelers seeking authentic, heartfelt American small-town experiences.