Stay in the heart of the city with Chicago rentals

With eye-popping architecture, world-class cultural attractions, and a burgeoning foodie scene, Chicago is a global city in every sense. While there is no shortage of hotels, checking into vacation home rentals in Chicago offers a unique chance to experience the iconic metropolis like a local.

The best neighborhoods for Chicago vacation rentals

Chicago is made up of more than 75 neighborhoods, each with its own unique flavor. Whether you're into bright lights and gleaming skyscrapers, hip cafes and indie record stores, or award-winning eateries and impossibly cool bars, finding your niche in Chicago is all part of the fun.

Stay on The Magnificent Mile

Anchoring Downtown Chicago, the Magnificent Mile is an urban wonderland of steel-clad skyscrapers, top-tier cultural institutions, and iconic public spaces. Vacation rentals in Downtown Chicago put you just steps from urban landmarks like the neo-Gothic Tribune Tower and 100-story John Hancock Center, dubbed "Big John" by locals.

Chicago rentals in The Loop

Home to a slew of postcard-worthy attractions, The Loop is the beating heart of Downtown Chicago. Check out the striking Frank Gehry-designed amphitheater and Cloud Gate sculpture in Millennium Park or head to historic State Street for swanky shopping. For the ultimate urban experience get sky-high with luxury Chicago vacation rentals in The Loop, where floor-to-ceiling glass windows unlock million-dollar views of the skyline.

West Loop, a foodie paradise

Sitting pretty on the banks of the Chicago River, West Loop has earned its stripes as one of North America's hottest dining districts. It's known as Restaurant Row for a reason, being loaded with everything from Michelin-starred restaurants to hole-in-the-wall pizza spots with cult followings. If you're planning a foodie weekend there's no better place to stay.

Different styles of Chicago vacation rentals

In a city of more than 2.7 million people, anything goes in Chicago. Sure, the city is awash with luxury apartments and lavish penthouses favored by Chicago's richest residents. But if you're travelling on a budget, need to house a big group, or simply prefer down-to-earth accommodation, you'll still be spoilt for choice.

Loft apartment rentals in Chicago

As a former industrial hub, factories and warehouses are plentiful in Chicago. Today, many have been reimagined as residential properties featuring lead-pane windows, soaring ceilings, and plenty of exposed brick and timber beams. Most champion an industrial-chic aesthetic and combine the city's gritty past and glamorous present.

Luxury apartments in Chicago

From beautifully renovated Victorian brownstones on the tree-lined streets of Lincoln Park, to ultra-modern penthouse apartments with dazzling views of the city skyline, when you experience Chicago through a luxurious lens you'll never want to go back. Premium apartments are always design centric and feature luxe décor and impressive attention to detail.

Studio apartments in Chicago

With plush beds, well-equipped kitchenettes and the occasional private balcony thrown in for good measure, studio apartments offer everything you need for a stellar stay in Chicago. Combining your living, dining, and sleeping space also translates to unbeatable value for money which makes studio apartments a top pick for budget travelers.

Party houses in Chicago

Heading to Chicago to celebrate a special occasion? Whether you're cheering on the Chicago Cubs at Wrigley Field, hitting up State Street for a shopping weekend or planning a bachelor party for the ages, party pads in Chicago offer enough space to house your whole crew. Get the festivities started with drinks on the rooftop terrace or a toast in your spacious living room.