New Eastside

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Entertainment

Bathtub

Hair Dryer

Toiletries

Bathroom

Dishwasher

Microwave

Freezer

Pod Coffee Machine

Fridge

Kitchen

Kitchen Utensils

Stove

Oven

Coffee Maker

Cooking Essentials

Kitchen & Dining

Dryer

Iron

Ironing Board

Washing Machine

Black-Out Blinds

Hangers

Bedroom & Laundry

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Lift Access

Paid Parking On Street

Self Check-in / Check-out

Private Entrance

Paid Parking On Premises

Parking & Access

Balcony

Outdoor

Pets Allowed

Pets

Smoke Detector

Child Friendly

First Aid Kit

Fire Extinguisher

Other

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 windows, ideal for admiring while you work at the desk or lounge on the sofa. The interior is unfussy, with chic details like giant rugs on the wooden floor and abstract are on the walls. Oh, and did we mention it’s pet friendly too, for those who can't bear to leave their pupper at home. The location is simply sublime too: in arty River North district, it’s close to Oak Street Beach, Michigan Avenue and Gold Coast, plus attractions like Millennium Park, Cloud Gate, and the Lincoln Park Zoo. It certainly ticks all our boxes.
 



Checking Account

Extra Pillows and Blankets

Free Parking

Free Parking On Premises

Barbeque

Carbon Monoxide Detector

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 memory foam mattresses in the bedrooms, the skyline is visible. Part of a block of aparthotels, the stay is perfect for those who want a little independence when visiting the city, with dining facilities and a sofa for socialising. Mornings start with coffee on the balcony, before hitting the nearby attractions, from Museum Campus and Grant Park to walks along Lake Michigan. If cooking is off the agenda on your return, it's only a short tube ride to Little Italy and its pick of homely restaurants.

Panorama Place

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 concentration of galleries in the US after Manhattan. You don’t have to be a culture buff to enjoy this slick two-bed home, however. With its stylish living room boasting floor-to-ceiling windows, a Smart TV and a stunning dining area with skyscraper views, you’ll have everything you need for a restful, relaxing stay in the Windy City. There’s even a dedicated workspace equipped with super-fast wi-fi in case you need to mix a bit of business with pleasure. The two bedrooms, each with memory foam mattresses, are a dream to sleep in, and you’ll relish crawling into bed after a day of seeing the sights. Aside from the galleries, the home is also close to plenty of shopping, restaurants, and nightlife options and many of the city’s best-known attractions are walkable, including Oak Street Beach, Millennium Park, the Cloud Gate and Lincoln Park Zoo. We think you'll agree, it’s a beautiful picture. 

Easel And Brush

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 most of the magnificent metropolis? Staying in this spacious apartment, right in the middle of the busting hub. Situated in the city's River North neighbourhood, the space offers unobstructed views of the locality with the Magnificent Mile just a short stroll away. Pack your bags, bring your pooch – they're allowed – and remember to bring your bring your favourite book – there's a cosy sofa and an even comfier bed to catch up on literature or take a well-deserved snooze. Just don't forget to make the most of your city-slicker home – after all, you're here to enjoy that glorious view. 

On Cloud Nine

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 Street Beach, Michigan Avenue and Gold Coast, plus attractions like Millennium Park, Cloud Gate and the Lincoln Park Zoo. In the apartment itself, you’ll find massive floor-to-ceiling windows with stunning views across the city. In the bedroom there's a desk, ideal if you need to catch up on some work, and a king-size bed (complete with a memory-foam mattress) for when you need to rest. After busy days, you'll be thankful for the fitted kitchen, making it easy to whip up your favourite meals – there's even a Whole Foods grocery store right downstairs for you to stock up on ingredients.


Savings Account

Library of Books

Board Games

Sound System

Toaster

Blender

Kettle

Cot / Crib

Cleaning Products

Exercise Equipment

Workplace

Fireplace

Rooftop Terrace

Patio / Terrace

Garden

Outdoor Seating

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 central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.

From the living space on the lower floor of this home, you will have access to a bright courtyard allowing fresh air to flow into the home. Here, you will also find a large sculpture created by a local artist and the staircase that will take you up to the rooftop terrace. Why not enjoy your morning coffee up here each day to soak up the fantastic views? 

Catch up on important work in the dedicated office space which features a Mac desktop, a desk which can be used as a standing or seated desk, plus great views through the windows in front of you. In this room, you will also find a live Peloton bike, perfect for working up a sweat and keeping fit during your stay.

Head out and explore the area including McCormick Place and Museum Campus, both of which are roughly five minutes away from the building. Then, in the evening, return to this home which is decorated with a real phone booth and modern art, and curl up in front of the electric fireplace, settle down with a great book in the reading nook, or even slip into a relaxing bath with a glass of wine in your hand. 

Chicago Morning

Parking Available

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-to-ceiling windows. The home is set up for both working from home and relaxing – there's even a Whole Foods on-site to stock up on supplies for dinner. In the evening, unwind on the comfortable couch in front of the flat-screen television. The living space is an ideal place to relax, decorated in neutral tones that are brightened up with plants and art. On the weekend, there's plenty to do nearby – walk to Oak Street Beach for a stroll in the sand, or check out some of the city’s best shopping, dining and entertainment that’s just footsteps away.

Monday Night

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. Start your day by firing up the coffee machine and enjoying an americano at the breakfast bar as you plan your day. If you have some work to do, you'll find a desk ready for you to set up your laptop, but if your day is free then perhaps you'll want to explore some of the nearby attractions, many of which you can walk to. The River North district has the highest concentration of galleries in the US, after Manhattan, and it’s also close to a lot of the sights that any visitor to Chicago will want to tick off, like Cloud Gate. Back at home there's a Whole Foods downstairs where you can pick up ingredients for cooking in the fully-equipped kitchen – but make sure you try out some of the local restaurants too. 

Local Colour

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, after Manhattan. You’ll also be next to Millennium Park, Ohio Street Beach, the Cloud Gate and the Lincoln Park Zoo. Stay in the thick of it, and rejoice in the apartment’s massive floor-to-ceiling windows, high-speed internet and memory foam mattress. You can cook a hearty breakfast ahead of a day’s sightseeing in the fully fitted kitchen (complete with a coffee machine and dishwasher). And at the end of the busy day, flop onto the couch and watch your favourite show on the smart TV before getting some top-notch sleep. The building has some extra perks too, like 24-hour security and a Whole Foods grocery store right downstairs. It’s practically a masterpiece in its own right.

Gilded Frame

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 – it's famous for its abundance of galleries and arty culture. You’ll be within walking distance of the luxurious Gold Coast neighbourhood too, where you’ll find tree-lined roads filled with upmarket boutiques. Luckily, you won’t have to go far to bring back your shopping, and you’ll be pleased to return to the comfortable sofa to rest your legs after a day out exploring. After preparing a home-cooked meal in the shiny kitchen, sit out on the balcony with a glass of something cold and watch the sunset over the city skyline.

Skyscraper

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, this home’s style could not be more fitting of its urban exterior. Greyscale met with colour and splashes of pattern epitomises the modern city-goer and stands out with its generous balcony – perfect for morning coffees. If you arrive here as busy as the commuters down below, dedicated workspace and high speed Wi-Fi is ready and waiting to make your life that little bit easier. But, if it's high speed entertainment you seek, you can be walking the likes of Oak Street Beach, Michigan Avenue, and Gold Coast all within minutes. After hours exploring Millennium Park, museums, even the Lincoln Park Zoo and onto glamorous bars and restaurants, you will be grateful for the generous, king-sized, memory foam mattress that awaits your heavy head to end the night. With everything at your fingertips, this is a stay to satisfy all creatures of culture and comfort. 

Slice Of Sky

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 reading through emails, or sit at the desk near the window with sprawling city views. After a busy day of working or exploring, nip down to the Whole Foods on-site to get supplies for dinner, and make use of the sleek, fully equipped kitchen. On free days, you’ll be ideally located to explore exciting, high-end parts of the city, with the Magnificent Mile, the Museum of Contemporary Art, and Millennium Park all nearby. We love the cosy vibe here – think thoughtfully curated plants and wall art, plus a flat-screen television – that really make this apartment feel like a home away from home.

Solo Bird

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 the bright blue armchair in the living room with sprawling city views. After a long day, the Whole Foods on-site makes it convenient to nip down for groceries before making yourself some dinner in the well-equipped kitchen. Thoughtfully curated art, plants and a flat-screen television makes this cosy flat feel like a home away from home. And with Oak Street Beach, Michigan Avenue, and Gold Coast just a stroll away, you’ll still feel like you’re on holiday.

Work & Play

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 the number of galleries within walking distance, while foodies will be just as excited to eat their way through the fantastic gastronomic scene. If you'd rather do some home cooking, there's a Whole Foods grocery store on-site, so darting out for those last-minute ingredients is a breeze. The home itself is a welcome retreat from the busy city below, and, unsurprisingly, the views are incredible. If you're in town for business, you'll find this home a peaceful and quiet space to work from – its ultra-high-speed wi-fi and comfortable furnishings are the cherries on top.

Bluegill

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 well as iconic sites like Chess Records, once home to legends like Chuck Berry and Muddy Waters. After a day out with the kids, head back to have a movie night on the comfy couch in front of the flat-screen TV, or have a glass of wine on the private terrace to take in stunning city views. We love the floor-to-ceiling windows here that fill the flat with sunshine, while the chic furnishings and fully-equipped kitchen make for an ideal home away from home.

I’m With The Band

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 the city. There's a fitted kitchen complete with coffee machine for those all-important caffeine hits, and a beautifully decorated living room and dining area where you can socialise, chill out or plan your itinerary in the Windy City. If you need snacks, there's a Whole Foods right downstairs, and did we mention that this home is pet friendly? One well-behaved dog or cat is welcome to join you on your travels. Located in one of Chicago’s most sought-after districts, it’s also close to plenty of swanky boutiques and top-notch restaurants, and many of the city’s best-known attractions are walkable, including the Museum of Contemporary Art and Millennium Park (home of Anish Kapoor's Cloud Gate, aka The Bean).

Designed For Life

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-speed internet and a dedicated workspace, as well as a convenient location within walking distance of a bus stop and an L train station. For those here to make the most of the city’s attractions, you’ll find that you can easily wander from your position in the affluent River North neighbourhood to sights such as the Magnificent Mile, the Museum of Contemporary Art and even Oak Street Beach. After a day out exploring, stock up on ingredients at the on-site Whole Foods downstairs, then rustle up a home-cooked meal in the kitchen. We recommend heading to the private balcony for sunset, where you can look out over the cityscape in perfect peace. 

Grey Marl

Balcony / Patio

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 before heading out for a day of adventures. You’ll be just a stroll away from both Grant Park and historic Chess Records, where legends like Chuck Berry and Muddy Waters once recorded songs. When you’re back, get cosy in front of the smart TV in the living room, or have a glass of wine on the private terrace as the city lights twinkle around you. We love the floor-to-ceiling windows that provide city views and lots of sunshine, as well as the chic decor and comfortable furnishings that’ll make you feel right at home. 

Swing Swing

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 work from home. If you find yourself with any spare time, you’re also ideally located to explore the city from your base in the trendy River North neighbourhood. Spend comfortable workdays at home amidst the thoughtfully curated plants and chic furnishings, while at the end of a busy day, the on-site Whole Foods has got your dinner needs covered. On the weekends, set out for adventures on foot. You’ll be just three blocks from the Magnificent Mile and six from the Museum of Contemporary Art, with a selection of Chicago's high-end shops, gourmet restaurants, bustling bars and nightlife on your doorstep. We love how easy it is to live here – with its fantastic location, fully equipped kitchen and thoughtful touches that make it feel like your home from home.

Modern Dream

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 with sprawling city views, to the chic breakfast bar in the kitchen. And on weekends, head out to explore the wonderful area, with high-end restaurants, shops and bars at your doorstep. We love how easy it is to just show up and start living here. There’s a Whole Foods on-site to make grocery shopping a breeze, and the thoughtfully curated plants, art and flat-screen television makes days when you want to stay in and relax cosy.

Solo Breeze

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 within walking distance from the Museum Campus and Art Institute – perfect for city-breakers and culture vultures alike. Making ingenious use of the space, the apartment has everything you need to feel comfortable, whether you’re a working professional or exploring the Windy City. Bathed in natural light from vast windows with skyline views, the interior benefits from minimalist furnishings, soothing tones of blue, grey and white, plus plenty of curated plants that create a homely ambience. After a spot of sightseeing, check out the glorious food downtown for a slice of the iconic deep-dish pizza. Just a short stroll away from Grant Park, you’re well-positioned for a working break or post-lunch meander. On top of that, picturesque Lake Michigan is mere footsteps from your home – it's safe to say you’re well in the loop here. 

Running Loops

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 sit and relax or work – including a desk in the bedroom, a dining table with city views, and a handy breakfast bar in the kitchen. After a long day, simply head to the convenient Whole Foods grocery store directly downstairs to stock up on supplies for dinner. Or, tie up your boots and pound the pavements, exploring Chicago’s food scene. On weekends, set out to explore the wonderful area you’re in – just three blocks from the Magnificent Mile and six from the Museum of Contemporary Art. We love the comfortable furnishings and thoughtfully curated plants and wall art here that really make the flat feel like a cosy home away home.  


River Style

Netflix

Amazon Prime

Rain Shower

Desk / Workplace

Throws

Nice to haves

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-made neon sign that hangs by the door – as soon as you step inside, your eyes will be drawn to the pinkish glow.

Whether you fancy working out on the Peloton bike or working from home at the desk in the second bedroom, this flat has something for everyone. The glossy kitchen has all the culinary get you'll need to rustle up something delicious, while the lavish spa-style bathroom is just the ticket after a long afternoon on your feet. Plop down on the caramel-coloured sofa, a refreshing cocktail in hand, and chill out with a movie night – Apple TV, Netflix, Disney+ and HBO Max are all available for you to use. Better yet, kick things up a notch with the projector in the main bedroom – we can't think of a better way to end the evening than snuggled up in the soft sheets, falling asleep to our favourite films. 

Another thing we love? The bustling locale, just a fifteen-minute drive (or twenty-five-minute ride on the ME) from downtown Chicago. Grab a bite to eat at the restaurants on 53rd Street (two blocks away), go for a jog around Promontory Point (a twenty-minute stroll), or spend sunny summer days relaxing by the lake at 57th Street Beach (twenty-seven minutes on foot).

Book a stay in one of the best homes in New Eastside

We selected the 46 homes worth renting in this location

Who's coming along?

Home spotlights in New Eastside

We selected the top 3% holiday homes in New Eastside

Most popular homes in New Eastside

Check upcoming rates & availability for New Eastside

Frequently asked questions