Vacation Rentals in Chicago

Home USA Illinois Chicago

Loading

Local Colour Holiday Home

Local Colour

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms Fancy trying out the lifestyle of a Chicagoan for a bit? Look no further than this cool River North apartment, which will make you feel right at home in one of the city’s most desirable districts. Sta... From €489 Nightly View Rental

Checking Account Holiday Home

Checking Account

Illinois, Chicago 2 guests 1 bedroom 1 bathroom Get out your Chicago apartment checklist and be prepared to get ticking as this apartment has all you need for your time in the Windy City. You'll find fantastic views through the floor-to-ceiling win... From €319 Nightly View Rental

On Cloud Nine Holiday Home

On Cloud Nine

Illinois, Chicago 2 guests 1 bedroom 1 bathroom Chicago isn't just known for its lively music scene and deep-dish pizza, but also for its larger-than-life architecture – after all, those skyscrapers speak for themselves. The best way to make the mo... From €338 Nightly View Rental

Bluegill Holiday Home

Bluegill

Illinois, Chicago 3 guests 1 bedroom 1 bathroom This home in Chicago's chic River North neighbourhood is set just three blocks from the Magnificent Mile and six from the Museum of Contemporary Art. Design lovers and art aficionados will appreciate... From €493 Nightly View Rental

Modern Dream Holiday Home

Modern Dream

Illinois, Chicago 3 guests 1 bedroom 1 bathroom This bright and breezy apartment is perfect for a couple looking for a change of scenery. The space is set up perfectly for the travelling professional – with plenty of desk space and fast wi-fi to wo... From €403 Nightly View Rental

Easel And Brush Holiday Home

Easel And Brush

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms If you’re visiting Chicago and you're interested in art, then the chic River North neighbourhood is the perfect place to stay. The area is now the city’s art and design quarter, with the highest conce... From €475 Nightly View Rental

Skyscraper Holiday Home

Skyscraper

Illinois, Chicago 3 guests 1 bedroom 1 bathroom Arriving at this home in downtown Chicago, you’re sure to be charmed by the typically Chicagoan high rise. Gaze down on the city above, and delight in the central location in the North River district... From €484 Nightly View Rental

I’m With The Band Holiday Home

I’m With The Band

Illinois, Chicago 6 guests 3 bedrooms 2 bathrooms This bright apartment located in the music hub of South Loop is perfect for a family holiday in Chicago. You’ll have options for outings galore, with jazz bars and restaurants at your doorstep, as wel... From €613 Nightly View Rental

Designed For Life Holiday Home

Designed For Life

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms It doesn’t matter if you’re in Chicago for work, rest or play at this two-bed in the hip River North district. The apartment has all that a family or small group of friends would need for a stay in t... From €467 Nightly View Rental

Gilded Frame Holiday Home

Gilded Frame

Illinois, Chicago 3 guests 1 bedroom 1 bathroom If you’re an art lover looking to visit Chicago, then you’ve come to the right place. River North, where this delightful one-bedroom is located, has the highest concentration of galleries in the US, a... From €413 Nightly View Rental

Self-Catering Chicago

Listing 1-10 of 23 Top Holiday Rentals

Vacation Rentals Chicago Top Destinations

Vacation Rentals Chicago Top Destinations

Holiday Homes & Accommodation Chicago

Chicago or popularly known as ‘The Windy City' is located on Lake Michigan in Illinois, and is one of the largest U.S. cities and a popular holiday destination. Stretch your neck towards the sky and take in the impressive skylines filled with skyscrapers and outstanding architecture.

Immerse yourself in the popular Art culture by visiting the Art Institute of Chicago, or walk through Millennium Park or even visit Lincoln Park Zoo. Chicago is famed for some delicious comfort food – sample some Chicago-style hot dogs and a deep-dish Chicago-style pizza.