Airbnb in Chicago

Airbnb in Chicago

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…

In this Airbnb guide to Chicago:

Is Airbnb legal in Chicago

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 Loop
Chicago Theatre, The Loop © Nejdet Duzen / Shutterstock.com

The Loop

Pros
  • The sightseeing
  • Theatre shows
  • Art galleries
Cons
  • 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!

Near North

Near North

Pros
  • The best of both worlds – city and suburbs
  • Well linked to The Loop
  • Lots of eating options
Cons
  • It’s a big area, so might be hard to navigate
  • Near North isn’t the cheapest

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.

River North
The Magnificent Mile shopping district © AevanStock / Shutterstock.com

River North

Pros
  • High-class dining
  • Upscale shopping
  • Close to everything
Cons
  • You’ll pay extra to be here
  • Really busy

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
Wrigley Field © Bret Habura / Shutterstock.com

Wrigleyville

Pros
  • The place to be for sports fans
  • Loads of sports bars
  • There’s a nice neighborhood feel
Cons
  • Gets super busy on game days
  • Around 30 minutes from The Loop’s sights

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

Old Town

Pros
  • Historic part of Chicago
  • Famous comedy venues
  • Vibrant neighborhood feel
Cons
  • Can be pricy
  • Not right in the thick of things

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
Wicker has good nightlife and a youthful vibe. © Page Light Studios / Shutterstock.com

Wicker Park

Pros
  • Off-beat bars
  • Eastern European culture
  • Vintage clothes shopping
Cons
  • A bit pretentious, perhaps
  • Getting pricier every year

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
Clark Street, Andersonville © Big Joe / Shutterstock.com

Andersonville

Pros
  • Lovely local vibes
  • Quaint boutique shopping
  • Good links to Lake Michigan beaches
Cons
  • Far from The Loop
  • You don’t get the big city feel here

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.

Bronzeville
The monument to the Great Northern Migration sculpture in Bronzeville, honoring the millions of African- Americans who moved northward from the South. © Thomas Barrat / Shutterstock.com

Bronzeville

Pros
  • Rich in African-American history
  • Soul food aplenty!
  • Summer cultural events
Cons
  • Not the prettiest part of Chiacgo
  • Not loads of Airbnbs

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.

Best Airbnbs in Chicago

Best Airbnb apartment in Chicago

Explore Chicago From an Urban Sanctuary With Free Parking

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.

Best Airbnb house in Chicago

Perfect Sanitized Lincoln Park Work & Play

Perfect Sanitized Lincoln Park Work & Play

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.

Best Airbnb for families in Chicago

Kasa Chicago 3BD2BA

Kasa Chicago 3BD/2BA

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.

Best Airbnb for large groups in Chicago

The Epic

The Epic

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.

Best Airbnb for quirky stays in Chicago

Sunny Character-Filled Apartment in Trendy Ukrainian Village

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.

Is Airbnb cheaper than hotels in Chicago?

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.

Hotel Julian

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.

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