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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.
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.
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.
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.
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.
Fly into Chicago O'Hare Intl. Airport (ORD), the closest airport, located 15.7 mi (25.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Chicago Midway Airport (MDW), which is 8.6 mi (13.9 km) away.
If you're traveling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations in the city. It's easy to get around Chicago by jumping on the metro at Monroe Station (Red Line), Monroe Station (Blue Line) or Adams-Wabash Station.
Chicago has plenty of regional specialties derived from the city’s working-class roots. In addition to the world-famous deep-dish pizza, popular dishes included thin-crust pizza, Chicago-style hot dogs, Italian beef sandwiches, the francheezie hot dog variation, and gyros. You can also find unique dishes from hidden gems in the city, all within reach of your vacation rental.
Chicago offers the perfect setting for a couple’s retreat. Romantic vacation homes can be found near places like the Lincoln Park Conservatory, a domed garden space with vibrant wildflowers and exotic plants, and the Chicago Theatre, a baroque-style auditorium with national musical and comedy acts. The North Avenue Beach, a popular lakeside beach with dining and shopping, is also great for couples.
Our 2022 property listings offer a large selection of 1,548 vacation rentals around Chicago. From 266 house rentals to 1,178 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.
Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chicago:
For other neighborhoods, please use our search bar to access the selection of vacation rentals available.
Vrbo offers a large selection of vacation rentals near lovely places in Chicago. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:
But there are many other points of interest around Chicago listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.
Yes, of course. Vrbo has 266 Houses in Chicago. Our other popular types of vacation rentals in Chicago include:
But you can also enjoy a great stay in one of our other vacation rentals including Studios and more.
Yes, you can select your preferred vacation rental with pool among our 342 vacation rentals with pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.