Chicago, IL, USA

Chicago, IL, USA

We found 868 vacation rentals — enter your dates for availability


Find the best place to stay — Chicago

Where to stay around Chicago, IL?

Our 2018 property listings offer a large selection of 868 vacation rentals near Chicago. From 477 apartments to 170 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chicago for a holiday or a weekend are on HomeAway.

Swept away by Chicago

With acclaimed architecture and a legendary food scene, Chicago is one of America's most iconic cities. Spend your time admiring public artworks, ticking off world-class museums and devouring deep-dish pizza. Wash it all down with sleek rooftop bars, hip microbreweries and elaborate craft cocktails. You'll also be just steps from some of North America's best urban beaches, so don't forget to pack a swimsuit. Feeling swept away by the Windy City? From sleek downtown condos, to trendy River North lofts, you'll find Chicago vacation rentals across the city.

Art and architecture in Chicago

Chicago serves up one of the country's best street scenes, with buskers, food trucks and public art on every corner. Don't miss Cloud Gate, a gleaming stainless-steel pod that's been famously nicknamed "The Bean" by locals. Chicago is also a champion for contemporary architecture. As you walk around the city you can admire Frank Gehry's futuristic Pritzker Pavilion, peer through the stained-glass windows of Frank Lloyd Wright's Robie House and gaze over the city from the Skydeck of Willis Tower.

Hop your way through Chicago's museums

Chicago is an art lover's nirvana, with a host of galleries to explore. You can check out Impressionist paintings at the Art Institute, get lost in kaleidoscopic colors at the Museum of Mexican Art and discover "outsider art" at the INTUIT gallery. Kids will love the Field Museum of Natural History, which is home to Sue, the world's largest Tyrannosaurus Rex skeleton. Perched on the lake, Navy Pier is another family favorite. Gear up for carnival rides, ice cream parlors, an IMAX theater, fireworks and more. Traveling with little ones? With spacious living areas and private kitchens, Chicago vacation rentals provide an ideal setting for family getaways to the Windy City.

Cheer on Chicago's sports teams

Summer is high season in Chicago, when the city enjoys long days and plenty of sunshine. You can also catch summer events like Blues Fest, which lures over half a million music lovers to Millennium Park. Late spring and early fall can be a great time to visit, with thinner crowds and every chance of beach weather. Chicago is home to multiple professional sports teams, with crowds flocking to big games. Whether you're watching the Cubs bat at Wrigley Field, the Bears score touchdowns at Soldier Field, or the Bulls shoot hoops at United Center, Chicago vacation rentals have you covered.

Get lost in Chicago's Millennium Park

From public parks to sandy beaches, Chicago doesn't scrimp on open space. Millennium Park is the undisputed showpiece, with public art, bubbling fountains and an enormous outdoor band pavilion. Not to mention an ice rink, botanic garden and enormous Great Lawn. Head down to the waterfront and you'll find over 25 beaches lacing the shore of Lake Michigan. You'll also see locals soaking up the sun in Lincoln Park, Chicago's biggest green space. It covers a 1200-acre footprint and is dotted with meadows, ponds, playing fields and the famous Lincoln Park Zoo.