Chicago is one of the greatest metropolises in the United States. In the heart of the Midwest, it’s known for its great industrial legacy, its moody jazz music, its cloud-splintering Art Deco skyscrapers and its fat pizza pies. A trip here is a whirlwind of delights. One moment you’ll be staring up at the soaring Willis Tower. The next you’ll be roaring on home runs in the hallowed ground of Wrigley Field. Priceless works abound in the world-famous Art Institute of Chicago, there’s more sightseeing and culture than anyone can handle within The Loop (the bustling heart of the town), and you’ve even got the beaches and state parks of Lake Michigan to explore on the outskirts.
Tempted by a trip to the Windy City? Be sure to check out Airbnb. There are thousands of listings on the popular sharing service that promise a stay with a difference in this Midwestern megalopolis. Booking is a cinch, with everything done online before you even arrive…
It sure is. There are some rules in place, though. Short-term letters all have to register with the local authorities in Chicago. Hosts should display their registration number on their online page, so potential guests can easily check that everything’s legit before they press book. You might want to steer clear of listings that are classified as ‘registration pending’ for added piece of mind. These are places that have applied for a permit but aren’t yet accepted, although they seem to be routinely used without many problems. Apart from those concerns, you’re free to browse, book and enjoy all the Airbnbs that the Windy City has to offer!
Where should I stay in Chicago Airbnb?
Ever heard of The Loop(1) ? It’s Chicago’s bustling, buzzing, beating heart. Around that, the chic and jet-setter areas of River North(2) can offer something a tad more refined, while the Near North(3) Side pushes just a little of the suburban feel. Old Town(4) has that down to a T, with pastry kitchens and kitschy little coffee joints. Then comes Wrigleyville(5) – the sportster’s mecca. Wicker Park(6) is to the north-west of The Loop, touting vintage threads and hipster bars. Andersonville(7) has a touch of Scandinavian character but also brings small-town America to the table. The South Side area of Bronzeville(8) is perfect for those interested in African American culture and Civil Rights history.
The busiest part of town
It’s packed, so Airbnbs aren’t too numerous
Every traveler who’s hitting Chicago for the first time should know of The Loop. A frenetic mishmash of Art Deco skyscrapers and uber-modern blocks, it encompasses all the most famous areas of downtown in one hit of world-class sightseeing, eclectic dining, and activity-filled days. Airbnbs can be hard to come by, because the place is the stomping ground of some of the city’s most prestigious attractions. The Art Institute of Chicago beckons with its Picassos in these parts, for example, while the Auditorium Theatre and Cadillac Palace Theatre bring a little bit of Broadway to the Windy City. Put it this way: You won’t get bored!
The Near North Side bridges the gap between the Chicago River and the Old Town. It’s a cosmopolitan little dash of the city, which offers a transition from tram-rattling hubbub to something more suburban. Essentially, the further north along the Lake Michigan shoreline you go, the more chilled things will be. Still, expect excellent transport links to iconic sights like the Willis Tower and get ready to experience a lived-in district that’s bursting with condos, steakhouses, sandwich delis – you name it.
No culture vulture or shopaholic in Chicago could possibly miss River North. This is where the action happens on the retail front. Mosey down to the south end of the so-called Magnificent Mile to see what we mean. There are designer names bursting from the department stores there, along with jewellers and haute fashion outlets. Food wise, River North is a doozy. Artisan food halls and cookery studios in theMART mall mean it can be hands on. Or just dip into one of the Michelin-starred restaurants for something truly special.
Wrigleyville is mainly known for one thing: Wrigley Field. That’s hallowed ground for supporters of the Chicago Cubs baseball team, and the whole district will go into overdrive whenever there’s a fixture on. Sports inspires much of the vibe around the blocks, too. Pool bars, pubs with oversized TV screens, and gift stores selling baseball caps and foam hands are everywhere. Delve below the surface and you’ll also catch a more chilled side of Wrigleyville, in farmer’s markets and Christmas fayres.
Old Town is where the suburbs of Chicago first took root. Settled by German farmers in the late 1800s, the district came to be known as ‘the cabbage patch,’ before going on to become a grand area for wealthy traders. They’re they ones who brought the prestigious Victorian homes you’ll see today down a few of the less-developed blocks. More recently, Old Town has risen to fame as a comedy hotspot (mainly thanks to the iconic Second City venue), and there’s an array of fantastic little neighbourhood delicatessens, ice-cream parlours and coffee stops.
Wicker Park is the central hub of a series of hoods that form Chicago’s coolest corner. On the north-west side of The Loop, they extend roughly from W Grand Ave to W North Ave. Within are all the retro vinyl emporiums, upcycled cafés, and vintage clothes boutiques you could ask for. Like a miniature Portland in the heart of Chicago, Wicker has good nightlife and a youthful vibe. It also spills into nearby Ukrainian Village, where Soviet-style milk bars await. Interesting stuff for curious travelers.
Andersonville gains plaudits for being super welcoming, super liberal, and an all-round nice place to be. Yes, it’s not very close to the heart of the Chicago you’ve seen on the postcards. However, this enclave on the north side of the city is about tasting laid-back Illinois vibes. Stroll down N Clark Street to encounter vintage bakeries and café-diners with a whiff of the 1950s about them. Check out the boutiques – locally owned tobacconists and bookstores are the name of the game here. Andersonville is also great for accessing the campuses of Northwestern University and the shores of Lake Michigan out of town.
One of the few districts on the South Side of Chicago to hit this list, Bronzeville is the classic home of African-American culture in the city. Despite a gritty backstory of economic boom and bust, it’s emerged as a major heritage hub for jazz and literature. Come to witness festivals like the Bud Billiken Parade – the largest African-American parade in the whole of the USA. Come to strut down Martin Luther King Drive and learn about Civil Rights and the Great Northern Migration as you go. At night, it’s all about spicy soul food and boogie clubs.
Explore Chicago From an Urban Sanctuary With Free Parking
Out in the vibrant northern suburbs of the Windy City, this Airbnb Plus has plenty of style and pizzazz. Its interiors fuse Midwestern industrial elements (exposed brick walls) with touches of Alpine coziness (check out that furry rug!), and the furnishings are a lesson in everything Scandi cool. More than that, it’s uber-functional and adds on a few luxuries – think a sun-kissed outdoor terrace and a premium coffee machine.
Cantered on a chic lounge that effortlessly blends the old and the new, this lovely home away from home whisks you to the vibrant bedroom neighborhood of Old Town. The piece de resistance is the salon, with its open fireplace emblazoned with folksy stencils and a hearth filled with flickering candles. Guests also get a utility room with laundry facilities, an open kitchen-diner, and a small outdoor terrace for those morning coffees.
This large apartment sits right on the South Loop – a cracking spot for jumping into all the sightseeing that central Chicago has to offer. It packs in a huge king-size bed, a queen, twins, and a pull-out sofa sleeper. Those join with a large lounge space that has floor-to-ceiling windows gazing out across the Windy City skyline. There’s also a fitted kitchen and a dining area with room for six people.
The Epic is a whole range of four adjoining loft apartments that can be rented as one to suit groups of up to 16 guests. Each is super stylish in its own right, with monochrome interiors and Scandi-cool kitchens. Together, they have access to a big outdoor terrace with views across to Chicago’s Art Deco tenement blocks, along with a communal gym and laundry facility.
Sunny Character-Filled Apartment in Trendy Ukrainian Village
You’ll score a stay right by the happening quarter of Ukrainian Village (an offshoot of hipster Wicker Park) at this Airbnb. You’ll also score a truly unique pad. It flaunts a prestigious Plus rating for its stylish interiors, which bring together elements of exposed brick and 1950s Pop Art. There’s a single bedroom, a fitted kitchen, and tonnes of artistic touches to keep the eyes busy.
People who book Airbnbs in Chicago often do it for the price. Not only do nightly rates in these private apartment and home rentals often trump that of hotels, but you can sometimes save a packet by picking pads with space enough for larger groups to share the cost. Airbnbs are traditionally self-catering accommodations, too (though not always). That means you could save even more in the Windy City by choosing to stalk the farmer’s markets and cook for yourself.
Don’t go thinking that Airbnb stays have the same high level of service as hotels, though. They’re much more hands-off affairs. To be greeted at reception, enjoy cool lobby bars, have on-site concierges and all those sorts of frills, you might be better off going for somewhere like the four-star Hotel Julian. It’s right in the thick of the action in The Loop and boasts modern rooms with a touch of the retro about them.
So, you’re looking to explore the Windy City? Great choice. This is one of America’s most bucket-list towns. Get ready for soaring Art Deco buildings and rich art collections, smoky jazz bars and shopping from sunup to sundown.