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Vacation rentals in Chicago

Discover Chicago’s best lake houses, luxurious rentals, and scenic getaways—perfect for a relaxing weekend or an adventurous stay on Lake.com.

Iconic Sculptures & Panoramic Views in Chicago

Chicago, IL, USA

Sunday
60°F16°C

Family-friendly

Pet-friendly

Luxury rentals

Tips on renting in Chicago

Getting Around

Nestled along Lake Michigan, the vibrant Gold Coast exudes timeless elegance. Stroll down historic Oak Street, where luxe boutiques like Chanel await. Indulge in culinary delights at Gibson's Bar & Steakhouse, then unwind at Oak Street Beach, where the gentle waves beckon.

What to Pack

As September ushers in Chicago's glorious autumn, expect crisp mornings and balmy afternoons, with temperatures ranging from 55 to 75°F. Pack a tailored light jacket for evenings, along with versatile layers to embrace the city's shifting moods. Don't forget sleek walking shoes for urban explorations and bring a stylish umbrella to navigate sudden showers during leaf-peeping strolls along the lakefront.

Must-Try Activities

Embark on a luxurious sailing adventure on Lake Michigan, where the skyline of Chicago glistens in the distance. Glide over azure waters, as you sip a fine cocktail, surrounded by vibrant sailboats at Monroe Harbor. Experience the city's captivating beauty like never before, framed by the shimmering waves and the sound of laughter echoing over the breeze.

Smart Spending Tips

Explore Chicago's magnificent architecture with a budget-friendly architecture boat tour for around $40 per person, then indulge in deep-dish pizza at Lou Malnati’s—about $25 per person. Enjoy a splash at Oak Street Beach, where relaxation is free.

In the vibrant heart of Chicago, where the glimmering waters of Lake Michigan kiss the horizon, adventurers awaken to the rhythmic dance of paddles slicing through the surface. The scent of sun-warmed cedar mingles with the distant laughter of families at North Avenue Beach, a beloved local gem where sun worshippers embrace both sand and surf. Beyond the popular beaches, the Chicago River invites explorers to embark on scenic kayak tours with institutions like Kayak Chicago, revealing the remarkable skyline from a unique perspective.

Take a leisurely stroll along the Lakefront Trail, where wildflowers bloom in spring, or glide through the tranquil beauty of the Skokie Lagoons, an enchanting habitat alive with birdsong. For a taste of local culture, stop by Little Village, savoring fresh tamales at a family-owned eatery.

As day fades into dusk, the shoreline festivals illuminate the city with live music and artisan stalls. Soak in the ambiance, and let whispers of the wind guide you to hidden treasures where every moment is an invitation—Chicago awaits your discovery.

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Frequently Asked Questions

Ready to see what Chicago has to offer? Let’s tackle some of the burning questions you might have as you plan your visit!

  • To visit Millennium Park in Chicago, arrive anytime between 6 a.m. and 11 p.m., taking advantage of the park’s daily hours. Start at the iconic Cloud Gate sculpture, then explore the interactive Crown Fountain and the serene Lurie Garden. Enjoy free events at the Jay Pritzker Pavilion, and in winter, skate at the scenic McCormick Tribune Ice Rink; in summer, this area transforms into an alfresco seating area. Entrance is free, making it an ideal destination for all seasons.

  • For a seamless and enjoyable boat launch experience on Lake Michigan in Chicago, head to the 31st Street Harbor. This vibrant marina offers a 3-lane boat ramp, ample parking for trailers, and a range of amenities including a fuel dock, laundry facilities, and sports rentals. Open from May to Labor Day, it provides fantastic access to the lake and is surrounded by the scenic Burnham Park and a brand-new playground with water features.

  • Yes, Chicago boasts several public marinas that cater to large boats. Burnham Harbor, the largest in the city, offers 1,126 slips and can accommodate boats ranging from 28 to 100 feet in length. Similarly, DuSable Harbor and 31st Street Harbor provide slips for boats up to 60 and 100 feet, respectively, with amenities like electrical power, water, and transient docking available from May to October.

  • For a captivating birdwatching experience near Chicago, head to Montrose Point Bird Sanctuary, where the iconic Magic Hedge offers a 3 km loop through promontory and dune habitats, ideal for spotting a diverse array of bird species, especially during the migratory seasons of April-May and August-October. Alternatively, visit Illinois Beach State Park, which features trails along the shores of Lake Michigan, providing a scenic 1.5-hour hike at an easy pace, with no entrance fees. For a more urban setting, Garfield Park’s western lagoon and surrounding trails are a hotspot, best explored during the spring and fall months.

  • For a serene park with panoramic views of the Chicago skyline, head to Milton Lee Olive Park, located just north of Navy Pier along the lakefront. This park offers unparalleled views of the city’s iconic skyline, making it a perfect spot for both daytime and nighttime photography. It is particularly beautiful during sunrise, though be prepared for chilly winds near the lake, especially on cold days.

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