Vacation Rentals in Chicago

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Solo Breeze

Illinois, Chicago 2 guests 1 bedroom 1 bathroom This studio apartment in stylish River North is perfectly equipped for both work and play. Spend a day at your home office with plenty of seating options – from the desk in the bedroom by a window wit... From €583 Nightly View Rental

River Style

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Your trip to Chicago just got a whole lot sleeker with this bright apartment in River North. Perfectly set up for as a base for exploring the city, or as a home office, you’ll have plenty of places to... From €810 Nightly View Rental

Running Loops

Illinois, Chicago 6 guests 3 bedrooms 2 bathrooms This stylish home-from-home is in Chicago’s artistic and culinary zeitgeist – South Loop. A cool and creative neighbourhood, known for its lively music scene, bold architecture and history, you’re wit... From €956 Nightly View Rental

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 €343 Nightly View Rental

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 €663 Nightly View Rental

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 €304 Nightly View Rental

Work & Play

Illinois, Chicago 2 guests 1 bedroom 1 bathroom Work from home with ease at this stylish apartment in Chicago’s trendy River North neighbourhood. You’ll have plenty of options from where to set up shop – from the breakfast bar in the kitchen, to th... From €275 Nightly View Rental

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 €753 Nightly View Rental

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 €379 Nightly View Rental

Solo Bird

Illinois, Chicago 2 guests 1 bedroom 1 bathroom This stylish River North studio is the perfect find for a quick business trip or city break in Chicago. Perfectly set up to work from home – you can sip a coffee at the chic breakfast bar while readin... From €365 Nightly View Rental

Self-Catering Chicago

Listing 1-10 of 23 Top Holiday Rentals

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.

Self-Catering Chicago, Illinois

Top 10 Holiday Homes in Chicago