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Self-Catering Chicago, Illinois

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.

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Are you a solo traveller or couple looking to stay in Chicago? Bookmark this page right now: you’ve found the right home-from-home with this one-bed in the arty River North district. It's close to Oak...

€160 /avg nightly

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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...

€160 /avg nightly

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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...

€87 /avg nightly

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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...

€191 /avg nightly

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Say hello to high-style city living at this sleek, serviced apartment in the heart of happening South Loop. Well-connected to downtown Boston, you’re never far from the Windy City action. Though with...

€152 /avg nightly

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Designed For Life

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...

€191 /avg nightly

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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...

€191 /avg nightly

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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...

€85 /avg nightly

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Checking Account

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...

€129 /avg nightly

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Convenience is key at this stylish apartment in Chicago’s trendy River North neighbourhood. From the moment you wake up in your plush, king-size bed you'll take in sprawling city views from the floor-...

€129 /avg nightly

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Whether you are staying for work or vacation, this high-rise apartment in trendy South Loop is perfectly located for all there is to eat, drink and do. Stepping in to look around at the chic decor, yo...

€163 /avg nightly

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Dusk in the City

Show up and start living the Chicago city life at this sleek serviced apartment in the buzzy residential neighbourhood of South Loop. With its crowd-pleasing restaurants, vibrant soul and jazz clubs,...

€202 /avg nightly

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If you're fed up with having to choose between a great location or a fabulous home, this striking apartment in South Loop delivers on both counts. Part of a contemporary building that marries glass, s...

€215 /avg nightly

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Escape the hustle of downtown Chicago with a stay at this sleek serviced apartment in the buzzy neighbourhood of South Loop. Well-connected to downtown Boston (seventeen minutes by metro, or eight min...

€241 /avg nightly

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The living is easy at this smart apartment complex located right in the heart of buzzy South Loop, a popular residential area just south of downtown. Jam-packed with expansive green parks, prestigious...

€153 /avg nightly

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Easel And Brush

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...

€191 /avg nightly

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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...

€160 /avg nightly

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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...

€88 /avg nightly

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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...

€257 /avg nightly

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Whether you’re staying for a business trip or to see the city’s sights, this home is ideally set-up for making the most of Chicago. For those needing to work, you’ll be delighted to find ultra high-sp...

€160 /avg nightly

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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...

€160 /avg nightly

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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...

€160 /avg nightly

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Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the m...

€257 /avg nightly

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Jazz about town from this charming apartment in Chicago’s South Loop – a music hub filled with live venues, restaurants and bars. Grab a morning pick-me-up at the in-building gourmet coffee shop befor...

€257 /avg nightly

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By the Citrus Tree

A duplex penthouse with two bedrooms, two bathrooms, and an idyllic terrace is located in Malaga's historic centre. What more could you want from a central city spot? Positioned just a few minutes awa...

€172 /avg nightly

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I’m With The Band

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...

€257 /avg nightly

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Surrounded by skyline and soaring scrapers, this city apartment boasts a central Chicago location that sets you up for an instant retreat. With artwork and windows out onto River North for decoration,...

€160 /avg nightly

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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...

€91 /avg nightly

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Let Yourself Go

Famed for its skyline punctuated by high-rises, indulgent deep dish pizza, pioneering house music scene and loyal sports fans, Chicago is one heck of a city. There’s no better place to sample Chicago’...

€171 /avg nightly

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All Things Glow

This apartment in Chicago's Hyde Park is positively flush with luxury touches. We love the trendy, timeless design, which merges mid-century pieces with a modern flair. Take, for instance, the custom-...

€423 /avg nightly

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Just a block away from Millennium Park and the Art Institute of Chicago, this neat little apartment puts you in the centre of the Windy City. It’s a three-minute walk to Millennium Park where you’ll f...

€126 /avg nightly

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Locations don't get much better than this. Set right in the heart of Greektown in the city's Near West Side, known for its excellent restaurants and friendliness, it's a fun, sociable place just a hal...

€230 /avg nightly

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The Jeweler's Gem

Snug yet stylish, this studio apartment is perfect for a lone traveller or couple wanting a cosy stay in Chicago. We love the sleek design and jewel tones – fitting, seeing as this flat is situated al...

€112 /avg nightly

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The nineteenth-century architectural firm Adler & Sullivan was responsible for some of Chicago's most celebrated icons, including the city's Stock Exchange Building, the Auditorium Building and the Ca...

€182 /avg nightly

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This swish Chicago bolthole is essentially a box of glass perched up high above the South Loop. If you’re in town for the game, Soldier Field is within easy walking distance, and the whole of Chicago...

€135 /avg nightly

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Bears In The Park

Located in Chicago’s vibrant South Loop neighbourhood, this bright and welcoming apartment puts you in an ideal position to explore some of the city’ most notable sights. Inside, warm wood floors and...

€157 /avg nightly

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Looking for a stylish bolthole in a buzzy pocket of Chicago? Then this smart studio apartment, located in the residential district of South Loop, might tick your boxes. With excellent transport links...

€138 /avg nightly

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Diamonds Are Forever

In an iconically Chicago building designed by Adler & Sullivan, this apartment sits amidst jewellery shops that have been trading since the 19th century and is just a couple of blocks from the sculptu...

€137 /avg nightly

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A hidden gem among the towering skyscrapers and bustling streets, the building was designed by Adler & Sullivan and is surrounded by jewellers, some dating as far back as 1872. It's fair to say you've...

€201 /avg nightly

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Flaming Saganaki

It's estimated that Chicago has the third-largest number of people with Greek ancestry out of any US city and nowhere is that seen more than in Greektown. In among the restaurants and museums dedicate...

€91 /avg nightly

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Chicago Morning

Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is centra...

€1,376 /avg nightly

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Lost in a Moment

This pad right in Chicago's South Loop puts the city at your fingertips. While foodies chow down at the many delicious restaurants on your doorstep, culture vultures can spend the afternoon roaming ar...

€153 /avg nightly

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This well-located city apartment sits sky high in a sleek building within Chicago’s chic River North district. Inside the design is cool and contemporary and offers plenty of space for cooking, dining...

€576 /avg nightly

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Above the bustling streets of Streeterville sits a modern home for modern travellers. A comfortable bed and mid-century-inspired furnishings create a pleasant and welcoming space, and thanks to floor-...

€106 /avg nightly

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Enjoy views of the Chicago River from the tufted sofa in your contemporary living room or from your wonderfully comfortable bed. Either way, comfort is guaranteed. Especially when you consider that th...

€122 /avg nightly

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Just imagine waking up to blissful views of the Chicago River from your undeniably comfortable bed, then getting up to pour yourself a cup of coffee in your stylish open kitchen and settling down on t...

€162 /avg nightly

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Northern Lakeview

Wake up to views of Lake Michigan from this sleek apartment, which features a free-flowing living and dining space and a light-filled bedroom with queen-size bed and floor-to-ceiling windows. Cooking...

€130 /avg nightly

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This studio apartment offers convenience and style in the heart of Chicago, with a fully equipped kitchen, enviable views and plush bed. You're welcome to make use of the building's amenities: on a ho...

€149 /avg nightly

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If you can't function unless you can feel concrete under your feet, this downtown apartment is your ideal base for a long-term stay in Chicago. Every care has been taken to transform the former indust...

€110 /avg nightly

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Bright & Breezy

At this modern home, high above the bustling streets of Chicago’s Streeterville neighbourhood, guests can expect ease and comfort. The home is fully equipped and ready for you to move in and with its...

€125 /avg nightly

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Self-Catering Chicago

Listing 1-50 of 54 Top Holiday Rentals

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