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The 9 most luxury Airbnbs in Chicago

Pamper yourself with a stay at some of Chicago's most lavish and luxurious Airbnb homes

Written by
Zach Long
Alex Floyd-Douglass
Danielle Goldstein

Who said vacations have to be boring and budget? It's alright to splurge on something lavish every now and then. We're talking amazing food, fancy drinks and, of course, luxurious accommodations. On your trip to gorgeous Chicago, consider looking for an upmarket Airbnb to truly complete your experience. You'll find plenty of enticing options, from converted architectural jaw-droppers to a gigantic rock star-worthy apartments.

We've tracked down a list of the finest choices, with features including expansive rooftop decks, gorgeous modern furnishings, four-car garages and arcade games. Plan an indulgent staycation or a fancy trip to the city by starting at one of these luxury Chicago Airbnbs.

RECOMMENDED: Best ideas for a Chicago staycation
RECOMMENDED: Best Airbnbs in Chicago

Who makes the cut? While we might not stay in every Airbnb featured, we've based our list on top reviews, hosts and amenities to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines. 

Luxury Chicago Airbnbs

The rock n' roll apartment in River North
Courtesy: Airbnb

1. The rock n' roll apartment in River North

If you consider yourself a bit of a rocker in your past life – or decade – stay in this awesome apartment. 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.

The modern loft in Fulton Market
Courtesy: Airbnb

2. The modern loft in Fulton Market

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 – and it really is. You'll find all the modern amenities you'll need, like a fully-equipped modern kitchen (for those awesome cooking skills of yours), 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. 

The Grand Kimball Lodge on Logan Square
Courtesy: Airbnb

3. The Grand Kimball Lodge on Logan Square

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.
 Wes Anderson core.
Location perks? 
In the heart of Logan Square. 
Budget range?
Spenny but worth it.

The rooftop penthouse in Old Town
Courtesy: Airbnb

4. The rooftop penthouse in Old Town

This 4,000-square-foot penthouse loft in Chicago's 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.

Tropical penthouse in Wicker Park
© Airbnb

5. Tropical penthouse in Wicker Park

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.

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.

The industrial-style loft on Madison Street
Courtesy: Airbnb

6. The industrial-style loft on Madison Street

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.

The designer home in Roger's Park
Courtesy: Airbnb

7. The designer home in Roger's Park

Looking for something to brag about at your next dinner party? This designer Airbnb in Chicago is the one. Considered an "architectural treasure", the Emil Beach House has so much to offer. It's one of the few Frank Lloyd Wright homes that you can enjoy with your family over a weekend – or more. With three bedrooms and bathrooms apiece, it has plenty of space for the whole family – including the outdoor garden which is filled with stunning landscaping for you to bask in the glory of your designer home. 

Rooms? Three. Sleeps six guests.
Mood? Architectural dream.
Location perks? A block away from Jarvis Beach.
Budget range? Expensive but worth the price.

Four-bed Hyde Park haven
© Airbnb

8. Four-bed Hyde Park haven

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.

The luxury family home in West Town
Courtesy: Airbnb

9. The luxury family home in West Town

Looking for a lavish home for your next family vacation to Chicago? This is the Airbnb for you. From the five grand bedrooms (sleeping up to 12 guests) to the fully equipped amenities, this Airbnb Plus home has it all. There's Wi-Fi throughout the house and the brick decor is classic Chicago-style – built in the late 19th century. There are also Grohe fixtures and 10ft ceilings to enjoy as you lounge around the four levels of this luxury home. 

Rooms? Five. Sleeps 12 guests.
Mood? Homey chic.
Location perks? Just a quick way away from some of Chicago's coolest restaurants and bars.
Budget range? On the pricier side of life. 

Find an Airbnb loft in Chicago


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