The 12 most luxury Airbnbs in Chicago

Sometimes, a vacation is just an excuse to splash some hard-earned cash, and in this home? You can do just that. And then some. With seven beds across five bedrooms plus six bathrooms and space for 12 guests, this luxury home on Chicago's Gold Coast can host the whole family and more. Not only is it incredibly easy to get to Lake Michigan from here (a serious win on the Gold Coast), this gorgeous property has all you need for a truly memorable stay. From plush furnishings and a fitness center to a glorious sundeck and indoor fireplace, you're spoilt for choice here. And well? As you should be. 

Rooms? Five. Sleeps 12. Six baths.
Mood? Dripping in luxury.
Location perks? An easy 10-minute stroll from Lake Michigan.
Budget range? Hella spenny.

If modern minimalism is your vibe (all encased in a three-storey brownstone, that is), then this stunning Airbnb is the one for you. Experience big city life to the fullest here in Chicago, where your designer penthouse offers space for 10 guests, two private patios and three beds and baths apiece. Whether you're here for work or with the fam, this stunning Chicago inner-city spot is the ideal home away from home – so good you'll never want to leave.

Rooms? Three. Sleeps 10. Three baths.
Mood? Minimalist luxe.
Location perks? Eight minutes from Lake Michigan. Dreamy.
Budget range? Surprisingly affordable for a Luxe Airbnb.

Formerly a Prohibition-era distillery, this early 1900s warehouse has been lovingly renovated into an industrial-style, open-plan living space. Inside you’ll find impressive timber ceilings, exposed brick walls, solid oak floors and bathrooms kitted out with Spanish porcelain tiles and fancy Japanese toilets. The kitchen has even won design prizes and features a 10-foot long stainless steel island and six-burner gas range so you can easily cook up a feast, while the cocktail bar is fully stocked with unique whiskeys, wine and craft beer. The hosts even used to operate a whole-leaf tea business out of the space, so you can sip on hand-plucked oolong and aged Puerh teas. 

Rooms? One. Sleeps two.
Mood? Industrial cool. 
Location perks? In Wicker Park where you’ll find plenty of cool coffee shops, boutiques, book shops, bars and restaurants.
Budget range? Mid-range price for two. 

Adorned in rock 'n' roll memorabilia, this Chicago Airbnb offers a whole lotta space to rock the night away. No need for an air guitar though – there are two real ones on the wall at your disposal. Other amenities include free parking, high ceilings, Wi-Fi, a SmartTV, and a fully equipped kitchen if you fancy cooking – although there's a vibey restaurant downstairs. The lavish Airbnb sleeps up to six guests in two bedrooms, so grab your pals and make it a weekend to remember. 

Rooms? Two. Sleeps six guests.
Mood? Rock 'n' roll for life. 
Location perks? Situated in River North – known as one of Chicago's coolest neighborhoods.
Budget range? On the pricier side.

Featured in Architectural Digest, this ultra-modern loft in Fulton Market has everything you need for a weekend of fun with your pals. With room for up to 12 guests to sleep over across 2,500 square feet, this two-bedroom, two-bathroom Airbnb is ideal if you're traveling with a large group. From the modern decor to the super tall ceiling, this place screams affordable luxury. You'll find all the modern amenities you'll need, like a fully-equipped modern kitchen, a Smart TV for when you're tired of exploring, and personal touches like ear plugs – for the light sleepers. 

Rooms? Seven. Sleeps 12 guests.
Mood? Luxury loft living.
Location perks? In the heart of the bustling West Loop neighborhood.
Budget range? Very well priced. 

Located in the heart of Logan Square, this four-bedroom lodge is the ideal Airbnb for a large group. Enjoy great amenities such as a large Smart TV, Wi-Fi, free on-street parking, and an open-concept kitchen and living space – before heading down to the hustle and bustle of Logan Square in true Chicagoan style. The interior is warm and welcoming, with dark wood and mid-century vibes. You'll find quirky touches and furnishings like a wall of sports equipment, exposed brick, and cool one-off pieces of furniture. It's a truly unique and very cool place to stay. 

Rooms? Four. Sleeps 10 guests.
Mood? Wes Anderson core.
Location perks? In the heart of Logan Square. 
Budget range? Spenny but worth it.

If you're looking for penthouses in Chicago on Airbnb, this 4,000 sq ft beauty in Old Town is one of a kind. The building itself was built back in 1897 – although completely renovated in 2017 – with original 120-year-old barn wood floors. As for the features, there are five bedrooms (four with king-size beds) and four full bathrooms. The master suite has a hot tub and steam shower while the kitchen is fully equipped with all you need to cook up a storm.

Rooms? Five. Sleeps 16+ guests.
Mood? Penthouse party ftw (just kidding).
Location perks? Literally next to Magnificent Mile.
Budget range? Sitting high on the boujie scale.

It's time to get the gang back together—all 14 members—because there's a tropical penthouse just waiting for you to live out your multicolored Miami dreams. This sprawling abode is absolutely bursting with colour, double height ceilings, neon art (there's even a bright pink shark) and quirky fittings and furniture. As well as the four sizeable bedrooms, there's an open plan kitchen-dining-lounge area and an outdoor terrace with mini palms and wicker furniture, to keep those Floridian vibes going. And if you're able to split the bill 14 ways, it's one of the best cheap luxury Airbnbs in Chicago you're likely to find. 

Rooms? Four, yet it sleeps 14. Wowsers.
Mood? Modern Miami Vice.
Location perks? Film buffs will delight in the knowledge that High Fidelity was shot around Wicker Park, where you'll find restraunts, bars and entertainment aplenty.
Budget range? Fill every bed and you're looking at less than $100pp per night.

Up for your very own private balcony overlooking the iconic Madison Street in Chicago? Check into this amazing Airbnb loft and relax in style as you overlook the mayhem below. Light up the indoor fireplace and snuggle up with a glass of wine before cooking dinner in the uber-modern kitchen. Relax in the bath before bedtime and enjoy the plush sheets on your comfy bed – or leave coziness behind and head out into Chicago's nightlife. It's worth it. 

Rooms? Two. Sleeps four guests.
Mood? Minimalist design.
Location perks? Walking distance from the gorgeous Oak Park.
Budget range? Suuuuper affordable.

This stunning modern brownstone has so much to offer. From multiple living areas to a well-lit basement gym and super snazzy kitchen, this property will make you and your friends (or family) feel right at home. There are four large bedrooms to choose from along with 3.5 bathrooms, providing plenty of space for you all to relax. Other fantastic amenities include an outdoor seating area, smart tech (even the fridge is smart), a juliet balcony in one of the rooms and a fireplace to cozy up in front of.

Rooms? Four. Sleeps eight.
Mood? Contemporary and comfy city living.
Location perks? A couple blocks from the verdant sprawl of Washington Park, but close to great food, cutting-edge culture and a lively nightlife scene in downtown Hyde Park.
Budget range? Mega bucks if you're staying alone, but a bargain if you're traveling with a crew.

Luxury airbnbs in chicago with a pool? We've got one right here that also happens to have skyline views and access to a gym – how could you say no? The appropriately named Cloud9 apartment will make you feel on top of the world, with beautifully designed interiors and a private balcony for outdoor drinking. The resort-style rooftop pool and spa are just the cherry on top.  

Rooms? Two. Sleeps five guests. 
Mood? Slick and contemporary. 
Location perks? in the heart of Lincoln Park and close to popular shops from Pottery Barn to Whole Foods. Old Town, the Loop and Wicker Park are easily accessible. 
Budget range? Worth going a little over budget. 

This sleek, contemporary apartment caught our eye for its old-timey charm. Who doesn't love a tweed rug now and then? Its thoughtful blend of retro and modern interior design makes the space characterful and cozy in addition to it being in a great neighbourhood - so close to the movies, park, zoo and of course, Wrigley Field. 

Rooms? Two bedrooms. Sleeps six.

Mood? Classy.

Location perks? Close to Wrigley Field, bars and dining.

Budget range? Not too shabby.