Chicago: Vacation Rental By Owner

This simple, modern one bedroom Hyde Park suite has a lot going for it: luxurious queen bed, full kitchen, spacious living area, and even a work corner and desk.... Read More

This studio apartment is ideally located for first-timers discovering the city and for regular visitors who want the easiest access to all of their favorite... Read More

This studio apartment is ideally located for first-timers discovering the city and for regular visitors who want the easiest access to all of their favorite... Read More

The Winchester House in San Jose, California? Notoriously haunted by restless spirits. The Winchester Suite in Chicago, Illinois? No spirits whatsoever, just... Read More

A touch of luxury. A glimmer of old-fashioned charm. Perched in one of Hyde Park’s most fashionable apartment buildings of the 1920s, this apartment demands just... Read More

This might be a studio, but don’t let that fool you—this space packs a powerful punch, with glorious floor-to-ceiling windows, an even glorious-er view, and more... Read More

When you rent this Wicker Park brownstone, you’ll be living in the high life. Two floors, two bedrooms, a huge kitchen with an island, tons of living space, and a... Read More

A refreshing, sophisticated oasis with added flare like vibrant, oversized works of Chicago memorabilia.  Ideal for a family or group of friends, this suite... Read More

A refreshing, sophisticated oasis with added flare like vibrant, oversized works of Chicago memorabilia.  Ideal for a family or group of friends, this suite... Read More

It’s always french-press-o’clock in this cozy, charming studio just off Belmont Harbor in the city’s eclectic Lakeview neighborhood. Sip your single-origin brew... Read More

Welcome to The Guild - one of the best Airbnbs in Chicago for big groups. This listing is 4 condos combined to create 1 full floor home for you. Please read our... Read More

Welcome to one of the best locations in Chicago. When you're here, we're excited to help you feel "Home Away from Home." Please read our FAQs to answer any... Read More

You have your own private entrance with a self check-in experience! Your space is separate with no shared common areas, so feel free to come and go as you please.... Read More

Unwind and enjoy the city in my Cozy and Clean Guest Suite! Guests have 2 beds/bedrooms, 1 bath, and a private entrance in back. There’s a desk to get some... Read More

Unwind and enjoy the city in our cozy and clean guest suite! We're super excited to begin having guests stay at our recently furnished guest space. We live... Read More

The best of Milwaukee Ave awaits only steps away while staying at this Chicago vacation rental. Enjoy countless hours perusing hip restaurants, cocktail bars, and... Read More

You simply can’t go wrong with this boldly chic studio. A sophisticated take on everything a studio can be, this apartment features rich hardwood flooring, modern... Read More

If Peter Lindbergh is your favorite European photographer (and you know enough about European photographers to have a favorite), look no further—we got you.... Read More

An unforgettable holiday in the Windy City awaits for a large family or group of friends in this 2,000-square-foot vacation rental apartment fit for 10! Located... Read More

Escape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full of natural light, the apartment features... Read More