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Chicago Pet-friendly rentals

Experience Chicago with a stroll along the vibrant Riverwalk, where art, dining, and skyline views await you.

Iconic Sculptures & Panoramic Views in Chicago

CoachHouse, Dunes Nat’l Park, 10 min hike to beach
Miller Beach, IN, United States of America
$284 night
Stylish cozy Bungalow near beach and Nat'l Park
Gary, IN, United States of America
$275 night
Dunes Nat’l Park, HotTub, Sauna, Firepit, Foosball
Miller Beach, IN, United States of America
$433 night
Huge yard w/ hot tub and firepit, dog friendly!
Gary, IN, United States of America
$165 night
Restful Refuge, Hot Tub, Firepit, Dunes Nat’l Park
Miller Beach, IN, United States of America
$718 night
Secluded Cottage, Hot Tub, Firepit, Fenced yard
Miller Beach, IN, United States of America
$163 night
Outstanding dune top views of Lake and Nat'l Park
Miller Beach, IN, United States of America
$885 night
SmartHome, Hot Tub, path to beach & Dunes Nat’l Pk
Miller Beach, IN, United States of America
$385 night
Beachfront Villa, Skyline view, Hot Tub, Smarthome
Miller Beach, IN, United States of America
$1,702 night

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.

Welcome to Chicago, a vibrant city where families can create unforgettable memories together. Begin your adventure at the Lincoln Park Zoo, a 35-acre haven that is home to more than 1,100 animals from 200 species. Stroll through the Pritzker Family Children’s Zoo, where young explorers can interact with farm animals and enjoy nature-themed play areas. For a taste of local culture, visit the Lincoln Square neighborhood, celebrated for its German heritage and charming boutiques. The Chicago Botanic Garden, a 385-acre paradise with 27 display gardens and five natural habitats, is the perfect setting for a leisurely family picnic.

Immerse your family in Chicago’s rich history at the Shedd Aquarium, where over 32,000 aquatic animals await. Watch penguins and dolphins at play, and let your children marvel at the colorful coral reefs. For a unique outdoor adventure, bike along the Bloomingdale Trail, a 2.7-mile elevated park that winds through vibrant neighborhoods and offers scenic city views. If your family seeks excitement, The Forge: Lemont Quarries Adventure Park features ziplining, ropes courses, and kayaking amidst breathtaking quarry landscapes.

Chicago’s culinary scene is a journey all its own. In the Logan Square and Avondale neighborhoods, enjoy a variety of cuisines at beloved local spots such as Cafe Con Leche and Lula Cafe. For a special treat, visit the historic Music Box Theatre, where family-friendly film screenings are often on the marquee. Venture into Wrigleyville to discover unique eateries and boutique shops tucked away from the usual crowds. From world-class attractions to hidden neighborhood gems, Chicago promises families a luxurious escape filled with adventure and lasting memories.

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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.

  • The 2025 Chicago Air & Water Show is taking place the weekend of Saturday, August 16 & Sunday, August 17, 2025. The event starts at 10:30 a.m. and ends at 3:00 p.m. each day. The show attracts millions of spectators, this extravaganza has been held annually since 1959 and has firmly established itself as the largest free show of its kind in the United States and it’s open to the public.

  • 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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Cottage on a lake