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The Ultimate Guide to Chicago's Old Town Neighborhood

Downtown Chicago is a jigsaw puzzle of neighborhoods and communities – each its own important little piece of the best metropolis on the planet. From South Loop to Westward Loop, Lakeshore E to Lincoln Park; each fits only right and plays its own unique role.

Only, I gotta say, Old Town is a standout slice of the Chicago neighborhood puzzle. Forget a rebirth – this celebrated neighborhood was hipster before hipster was a thing.

Hello, Old Town

Former Boondocks takes its neighborhood status and so seriously, you can actually feel the neighborhood-iness in the air. Just take a stroll down its tree-lined sidewalks and y'all'll get a sense of the community that'south so frequently lost in urban neighborhoods.

And I'k telling you lot, this location cannot be beat out. Old Boondocks sits less than 2 miles northward of the heart of downtown Chicago and but a mile westward of the lake. Its neighborhood neighbors (yup, that's a thing) include Gold Declension to the due east and Lincoln Park to the north. Pretty proficient company, right?

The verbal boundaries of Old Town…well, those depend on who you lot ask. The unofficially official borders, according to the City of Chicago data portal (and the almighty Google), look like this –

Map of the Old Town Neighborhood Border
Onetime Town Chicago neighborhood borders

The neighborhood comprises sixty-4 acres, its original and modern borders split by North Avenue, running straight through the centre. The part of the neighborhood known as the Old Town Triangle – every bit it has been known since the 1950'south – takes its throne atop this jewel of a 'hood.

Map of Chicago's Old Town neighborhood and Old Town Triangle
Quondam Town Triangle department of Chicago'southward Old Town neighborhood

Now, locals may say – "whoa, wait…half of that is Lincoln Park." And you know what? They're right. Depending on who y'all ask, a good chunk of Old Town that lies due north of North Avenue is as well considered Lincoln Park. Information technology's cool, we're all friends here!

Old Town is a pretty minor area, even using Google's generous borders, measuring one mile north to south and simply shy of a mile e to west. Run the perimeter and you lot'll have a 5k under your belt.

Erstwhile Boondocks History

The Cabbage Patch

Retrieve history lessons are wearisome? Not this one. First, imagine this humming urban neighborhood equally it once was – a cabbage patch. No really, that's what it was originally called…the Cabbage Patch. This was pre-Civil War when German settlers beginning adult the area and fifty-fifty before Old Boondocks was even within Chicago'due south city limits.

It was those German settlers who built the neighborhood'south greatest treasures – St. Michael's Church.

St. Michael's Church in Chicago's Old Town neighborhood
St. Michael'due south Church at the intersection of Eugenie Street and Cleveland Avenue

This iconic structure was congenital in 1869 and just a few years later, survived the Great Chicago Fire. The rest of the neighborhood, however, didn't fare so well. Near every home and structure burned to the ground and Former Town was left to rebuild.

A New Old Town

The rest of Chicago took the clean slate every bit an opportunity to create a logical grid of perfectly straight streets running east, west, northward and south. I'd like to personally give thanks these visionary metropolis planners for creating a street system that makes it nigh impossible for even its most geographically-handicapped residents to get lost (that's me!).

But – One-time Boondocks was an exception. Postal service-burn, the Triangle kept its original willy-nilly street layout. These winding streets, total of narrow one-ways and asymmetrical intersections, nonetheless be today and are key to the neighborhood's charm.

Throughout the following decades, new fire-resistant brick, stone and stucco homes were built up and down the winding streets. The German builders made eclectic choices and took pride in creating masterfully-crafted row houses and flat buildings. Gothic windows, Victorian spires, insanely-ornate balusters and spindles, swooping roofs…the listing goes on and on.

Historic brownstones in Chicago's Old Town neighborhood
Historic brownstones in Old Town (photo credit: Victor Grigas )

These century-onetime homes still stand up today and are the cornerstone of Erstwhile Town. If you find yourself with a gratis afternoon, take an Old Boondocks Architecture Tour. Tourists and locals alike will marvel at the history.

The Triangle Comes Together

The Great Depression was hard on Former Town and it fell into a state of…well, depression. Disheveled and dirty, the once-lovely neighborhood was in jeopardy of losing its identity.

But in the 1940s, its residents rose up to take back the neighborhood and make information technology shine one time once more. They banded together and formed the Old Town Triangle Association; a super-active community system that'south headquartered in the Triangle to this day.

1 of the first projects the Clan undertook was to hold a minor Art Off-white. They figured the artisans in the neighborhood could sell their art and the community would open up its doors to invite visitors to notice their hidden precious stone of a neighborhood. And thus, the confront of Old Boondocks changed forever.

People browsing art at the Old Town Art Fair in Chicago in 1968
The Old Town Art Off-white in 1968 (photo credit: Victor Grigas )

The curious visitors; they came. And stayed. The One-time Town Art Fair, which is still held in June each twelvemonth, brought a new wave of residents to the neighborhood. Immature suburbanites, hungry for change, transplanted to Old Boondocks. As the neighborhood grew, information technology became the mecca of bohemian culture. With its popularity came other changes too – rents began to tick up, small business organisation opened store and Wells Street was born.

Due north Wells Revolution

Up until the 1960s, the Triangle truly was Sometime Town. But as the neighborhood grew, N. Wells Street – which runs vertically through the neighborhood – became the place to see and be seen. Strolling up and downward the street today, you can still get a sense that this place has a story to tell. And information technology does!

The Old Town School of Folk Music opened on Wells in the late 1950s and was the catalyst for an explosion of development. The area became a sanctuary for local musicians and artists and also drew suburban visitors who wanted to experience the hippie haven for themselves.

Throughout the next 2 decades, iconic restaurants, music joints and just-plain weird attractions opened their doors up and down Wells. Ask anyone familiar with Former Boondocks of the 1960s and 70s and they're sure to reminisce about noshing on gratis pickles at The Pickle Barrel and wandering through the Royal London Wax Museum. If they were lucky, perhaps they defenseless music icons like Steve Goodman and John Prine jam at The Earl of Old Town Buffet & Pub.

A photo of N. Wells Street in Chicago's Old Town neighborhood in 1965
A snapshot of life on N. Wells Street in 1965

Unique shops peppered the street every bit well. Stores hawking candles, jewelry, records and fifty-fifty peace pipes. Y'all tin practically scent the patchouli in the air, right? The starting time Crate and Barrel store – a far cry from what it is today – opened its first store on Wells in 1962.

Shops, pubs and restaurants came, went and evolved into the energetic Old Town of today.

Old Town Today

The Old Town of today has the same unique qualities of its former self. Longtime residents have stayed put and the Quondam Town Triangle Association is more agile than ever. Considering of this, the neighborhood has been able to proceed its amuse and unique characteristics while still embracing inevitable modify and development.

Today yous'll find bohemian chic on one corner and timeless charm on the next. Luxury high-rises and mid-rises mingle with brownstones and historic Victorians and neighborhood shops share the block with franchised conveniences.

A photo of a corner in Chicago's Old Town neighborhood
The Old Town neighborhood today – old, new and always mannerly!

And, Onetime Town's residents know just how fortunate they are. They get charm on their doorstep and everything the metropolis has to offering is simply a hop, skip and a jump away. Quondam Boondocks gives it's lucky residents the comfort of a hometown smack dab in the middle of Chicago.

North vs. South

So, yes – Old Town has a fantastic location and a magical neighborhoodiness vibe that'south practically priceless, but what'southward it like to live in that location?

The area to the south of North Artery, on either side of Wells Street, is e'er humming. On the south border you'll find luxury high-rise apartments and everyday conveniences. When your dentist, grocery marketplace and drug shop are all within walking distance, life is just easier.

Construction of Old Town Park, a luxury apartment building in Chicago's Old Town neighborhood
Construction on Sometime Boondocks Park, luxury apartment towers on Division Street

Simply this southward-of-the-north-border department of One-time Town is charismatic as well. Cipher upwards Wells Street a couple blocks and yous'll be greeted by the fe Old Town gates.

The Old Town gates in Chicago's Old Town neighborhood
N. Wells Street, simply north of W. Sectionalization Street

Block past cake, modern amenities of the city fade and the Erstwhile Town of yesteryear emerges. Due north. Wells Street is littered with endless pubs, cafes, shops and boutiques. The narrow streets that criss-cross Wells are laden with brick apartment buildings and swooping trees.

Cross North Artery, and you're officially in the historic Onetime Boondocks Triangle. Detour off Wells to discover a treasure trove of historic homes and buildings. Call me a nerd, only this is ane of my favorite things about Erstwhile Town. I've spent entire afternoons drifting up and down streets, oogling gorgeous front doors and wrought atomic number 26 balconies.

Modest Business Fundamental

This 'hood is all about small business and dwelling to independent java shops, pastry shops, cafes and more than. Treat yourself to local favorite Cocoa + Co. Y'all should skip the java and go direct for a night hot chocolate (holy yum). Intelligentsia Java which is south and closer to the new loftier-rises, is the perfect spot to settle in with your laptop and become caffeinated while working.

Old Town Chicago's Village Cycle Center
Famous Hamlet Bike Heart on N. Wells Street – sells bikes on three floors and over 30,000 foursquare anxiety of space! They're the nation'due south largest bicycle shop and have been in Quondam Boondocks since the 70s.

The breadth and depth of shops and boutiques in Old Town is super eclectic. My favorite section of Wells has a spice shop called The Spice House which is unmarried-handedly responsible for me finally taking up cooking. With thousands of spices and blends packed into the cutest piddling store, I could spend hours peppering the staff with questions.

Conveniences

Yes, I love those independent shops and boutiques but if there's one matter I cannot alive without it's Target. Fear not, bullseye lovers, at that place is a Target but a squeak outside the official boundaries of Old Town in the southwest corner on Sectionalization Street.

There are killer grocery market place options right in the neighborhood too:

  • Marianos: full-service grocery on Clybourn Artery
  • Jewel Osco: full-service grocery betwixt Clybourn and Sedgewick
  • Fox Trot Market: Grocery and Cafe on Wells near N Artery
  • Plum Market: local favorite. Speciality grocery between Segmentation and Scott Street
Plum Market in Chicago's Old Town neighborhood
More than organic groceries, Plum Market also has wine tasting at their in-house bar, The WineBar

Drugstores are conveniently located as well; a Walgreens in the heart of the neighborhood on Wells and North and a CVS tucked into the corner of Clark and Sectionalisation.

Onetime Town Rental Backdrop

Are you sold on living in this full gem of a neighborhood yet? There are several luxury apartment buildings in the One-time Town neighborhood, and more on the way.

Northward+Vine

This beauty is brand-new and whoa – you're going to love it. Due north+Vine is located on N Avenue on the westside of Old Town. Information technology's 11 stories and 261 units of pure minimalist magic with all the bells and whistles. These apartments brand maximum apply of infinite with smart-meets-beautiful design. Bring your pup; this building is dog-friendly and even boasts a pet-spa and dog run.

North + Vine, a luxury apartment building in Chicago's Old Town neighborhood
North+Vine luxury apartments on Due north Avenue in Sometime Boondocks

Sometime Boondocks Park

Old Town Park is right in the heart of the activeness on Division Street. The first belfry, which opened in 2018, was joined by its twin in 2020. A third and final tower is currently nether construction. The views this edifice offers are out-of-this-world and the details and civilities are a dream. Floor plans range from convertibles to unimaginably gorgeous penthouses.

The interior of a luxury apartment building in Chicago's Old Town Park's second tower.
Beautiful living at Old Town Park's Belfry Ii

1325 N Wells

Life is a fiddling more fun when you lot live right on Wells. This gimmicky midrise, which opened in 2019, lends luxury living smack dab in the center of Old Town. You'll love the location, information technology's pet-friendly policies and rooftop lounge puddle.

And…Quondam Town continues to grow. There are two new residences coming soon, and we're certain more are on the horizon:

  • Sometime Town Residences – Opening in 2020
  • 1355 N. Sedgwick – Opening in 2020

Best Restaurants in Old Town

The eating house scene in Old Town is on point. Wanna grab the best burger in Chicago? It's yours. Italian to Mexican and cocktails for days – I promise you…this neighborhood volition not let you get hungry, or thirsty.

Best Italian: Topo Gigio

Located on Wells Street, this award-winning Italian eating house is the real deal. The authentic ambience, charismatic staff and homemade pasta will take you coming dorsum again and again.

Best Quick Bite: Pocket-size Chevel

That "all-time burger" – information technology's hither! Don't let the term "quick seize with teeth" fool you lot – you lot're gonna savor every last bite at Small Chevel. This quick service version of Westward Loop's Au Chevel, is an Old Town treat. A seat on the patio (right in the action on Wells Street) with a cheeseburger in hand equals a picture-perfect lunch.

All-time Brunch: Criterion

This ain't no overnice breakfast, merely a "last dark was likewise much fun and we need to recover" kind of brunch joint. In fact, at dark, Criterion is a bar-meets-dance club only come daylight, it serves up the craziest bunch buffet. I'm talking most a donut wall, carving station, waffle bar, omelettes, oysters, mac and cheese…the list goes on. Oh, did I mention bottomless mimosas? And the wait staff is bright-eyed and absolutely lovely, which is a care for on a Sunday morning.

Best Dessert: Jeni'south Splendid Ice Cream & La Fournette

Choosing between Ice cream and pastries? No thanks. Nosotros take a tie here, folks.

First up – Jeni's Splendid Ice Cream on Due north Wells. This Ohio-based artisan ice foam shop has eight Chicago locations (and growing!) and Quondam Town is lucky to call 1 theirs. Prepare yourself to expect in a line out the door anytime the temperature is above 50 (hey, we're Chicagoans). But, it'south worth information technology. Insider pick: the goat cheese with red cherries in a sugar cone.

Jeni's Ice Cream in Chicago's Old Town neighborhood
Jeni's rotating option of crazy-practiced ice cream will have you coming back once more and once again

Next – La Fournette. Oui, oui, oui! I would pay for the smells alone at this French bakery. With accurate roots (the French owner is a Earth Baking Champion) and pastries that literally melt in your mouth, La Fournette is a Wells Street precious stone. Locals return again and again for  the almond croissant, only I'k a sucker for their macarons.

All-time Fusion: Forestero

This casual little joint, located on North Artery betwixt Hudson and Cleveland, serves upward Asian-fusion goodness that'll go along y'all coming back again and once again and again. The Korean flavors are for real, guys (I could live off the Bulgogi alone) but their twist on traditional dishes is what I love virtually. Order the kimchi fries and wash 'em down with a horchata.

One-time Town Bars and Nightlife

Cold beers to craft cocktails – Old Town'due south got yous covered.

Best Dive Bar: One-time Boondocks Ale Firm

This iconic bar has been in Quondam Town since 1958, and it shows. Anthony Bourdain called it the best dive bar in Chicago, and he'south right. This bar has not kept upwardly with the Old Town gentrification, which is all the more reason to beloved it. Cozy up to the bar, grab a cold beer and take in the old school vibe. Leave your plastic at home, Old Town Ale Business firm is cash-merely.

The historic Old Town Ale House in Chicago's Old Town neighborhood.
The One-time Town Ale Business firm: "The best bar in the world that I know about" – Roger Ebert

All-time Wine: Glunz Tavern

Located near Division and Wells, the Glunz Tavern is part specialty liquor shop (Business firm of Glunz), office bar and restaurant and has a staff of experts on all things booze. It's my favorite spot in the neighborhood to grab a glass of vino because it just feels so Old Town. Information technology'south no surprise since the tavern-fashion bar was actually restored by the granddaughter and swell-grandson of Louis Glunz (the original owner) descendants in 2012.

Arts and Entertainment

Art Festivals

Quondam Town's heritage is ripe with art and entertainment – from the first fine art fair to the mid-century music scene to the opening of the famous 2d City comedy club, the neighborhood has intentionally held onto it's art-centered roots.

Old Town Art Fair

The Old Town Art Fair has been an annual event for over seventy years now! The result, organized past the Onetime Town Triangle Association, is held the second weekend of June each yr up in the Triangle. The art fair has come a long style from its humble ancestry with crowds flocking from near and far to nourish 1 of the best art shows in the country.

Crowds at the Old Town Art Fair in Chicago
Packed shoulder to shoulder at the One-time Boondocks Art Fair (photo credit: Victor Grigas )

Over 250 juried artists are invited to participate each year and it'south estimated over 30,000 visitors attend. And, it'south more art that draws attendees. I'k a huge fan of the Garden Walk, which lets you explore all those beautiful vintage homes around the original Triangle without looking like a Victorian domicile stalker.

There's alive music too – jazz and folk, naturally. And the nutrient…oh my. Come hungry, and thirsty!

Wells Art Festival

Expect a infinitesimal…another fine art off-white?! Yes! The Wells Street Art Festival is held the same weekend as the Old Town Fine art Fair (second weekend in June) and takes identify on N. Wells Street between North and Sectionalisation.

A little less peace-dear-and-flower-gardens than its neighboring fair to the north, this festival is all about fun and amusement. Created by the Old Town Merchants and Residents Association, the festival has 200+ fine art vendors and raises over $300,000 for Old Boondocks community causes like hunger initiatives and workforce programs.

The atmosphere is more stone and whorl, with live music lasting into the evening hours.

Comedy Cardinal

Just when you thought Onetime Boondocks couldn't get more colorful, information technology does, with this unexpected legacy: Comedy! It's comedic history dates back to the 1950s and the laughs just continue coming.

The Second City

If you lot know Chicago, yous know The Second City. The iconic venue opened in 1959 and with it, brought a comedy culture – and comedy superstars – to Erstwhile Boondocks. Information technology's been in the same location, on North Wells, since the mid-sixties and has grown from a cabaret theater to a legendary improv venue, school and global brand.

Whether you're a Chicago native, newly resident or tourist, catching an improv show at The 2d City has gotta be on your saucepan list.

The Second City in Chicago's Old Town neighborhood
For over lx years, The 2d City has brought laughs and one-act greats to Quondam Town

The 2nd Urban center isn't the just one-act player in the neighborhood. Zanie's has headline comedians on phase 7 days a week. Up Comedy Club, owned past The Second City, has a rotating evidence line-up ranging from improv to stand-up to autumn-down-funny skits.

Old Town Demographics

Data always tells a story and these Old Town demographics paint a motion picture of the community:

  • Population: 39,019
  • Median Age of Population: 33.six
  • Total Households: 23,269
  • Average people per Household: two
  • Households with children: 10.five%
  • Owner-Occupied: 39.eight%
  • Renter-Occupied: 60.ii%
  • Average Household Income: $136,254 annually
  • Median Household Income: $86,803 annually

Parks and Greenspace

Because Old Town is so dense and urban, public green space is sparse. Only, that doesn't mean its residents don't become out and enjoy the outdoors. Take one lap around any block in Old Town and you'll run across at least three French bulldogs (okay, I kid…kinda). So yes, One-time Town is super dog-friendly and appeals to their humans who prefer the exterior to the within too.

Old Town Residents have admission to tons of parks that aren't IN Erstwhile Town, simply then close, you can telephone call them your own.

  • Seward Park – just blocks from the newer luxury apartment along Segmentation Street, this seven-acre park has lots of greenspace to run and play, plus community gyms and an indoor swimming pool.
  • Hudson Chess Park – this unique little park sits in the Sometime Town Triangle. The chess tables are quaint, but it's the statuary statue of Hansel and Gretel, which honors the Triangle'south German settlers that adds real amuse to this little corner of the neighborhood.
Hudson Chess Park in Chicago's Old Town Triangle
Hudson Chess Park in the Sometime Town Triangle
  • Bauler Playlot Park – a kid-friendly park, with a play construction, just due north of the Triangle in Lincoln Park.
  • Sedgwick Park – tucked between historic brick apartment buildings, this lilliputian park is located in the Old Boondocks Triangle. It has a small play structure and in archetype Old Town style, an art installation featuring two lifesize modern metal horses.
  • Lincoln Park – this massive, i,100+ acre park lies just on the east side of N. Clark. A big bonus for families – Lincoln Park Zoo is merely a fifteen infinitesimal walk from the eye of the Old Town (maybe twenty minutes if y'all're pulling a railroad vehicle).
  • North Avenue Beach – if you love to spend summer with sand between your toes, the lakeshore is just i mile away.

Neighborhood and Business Associations

In that location are two active neighborhood associations in Old Boondocks:

  • Old Town Triangle Association – an engaged community of neighbors, this celebrated association is focused on preserving Sometime Town's celebrated district, neighborhood improvements, capital comeback, the Quondam Town Fine art Off-white and other fun events that bring the community together.
  • Sometime Town Merchants & Residents Clan – residents and business organisation owners team together to keep Sometime Town "prophylactic and vibrant." The group'due south main focus is on the area in and around N. Wells, only whatever Old Boondocks resident or business organization can bring together.

Schools (K-12)

  • Franklin Fine art Middle – this 1000-8 public schoolhouse is Chicago'southward only citywide magnet school for the arts. A modest student population (under 400 pupils) and a focus on drama, trip the light fantastic toe, music and visual arts brand this unique public schoolhouse an first-class and convenient option for Quondam Town residents.
  • Manierre Public Uncomplicated Schoolhouse – a PreK-8 public school with an emphasis on "Higher, Careers and Civics". The omnipresence boundary covers the part of Old Town southward of Due north Avenue.
  • LaSalle Language University – located in the Quondam Town Triangle, this K-8 public magnet school focuses on civilisation and language.
  • Catherine Cook Schoolhouse – a individual, Pre-Thousand-8 school located but off N. Wells on Schiller Street. This community-centered school  "empowers students from preschool through eighth course to be adaptive, confident and productive stewards of an evolving world."
  • Immaculate Conception St. Joseph School – this private, Cosmic parish school is located in the center of Old Town, only a block off N. Wells on N. Park Avenue. It has two campuses and 450 students in grades preK-8.

Parking

I'm non gonna sugarcoat it, parking in Old Town is a less than joyful experience. Between the congestion and narrow streets, information technology's not easy. The central to headache-free parking is to be prepared. Sure, you might snag coveted street parking (a meter volition run yous $4.l an hr) merely using a service like ParkWhiz makes finding and prepaying for parking a breeze.

Public Transit

Luckily, if you want to live a car-free life in Onetime Town, Chicago's public transit options make it piece of cake.

Commuting in and out of the neighborhood is simple using the CTA Brown and Purple lines out of the Sedgwick Station. The Red Line can also be accessed along the southwest corner of Onetime Town at the N/Clybourn Station.

Bus stops, located on nigh every corner, are a super convenient way to fizz around the neighborhood and beyond, especially during chilly winter months.

Map of the subway lines in Chicago's Old Town neighborhood

Highway Access

Sometime Town is tucked into the metropolis, but it's easy enough to find your mode to major highways. US-41 (Lakeshore Bulldoze) is a couple-minute bulldoze east. The easiest manner to hop on is to take North Avenue to N. LaSalle Drive.

Admission to I-90 is 2.5 miles due west along Segmentation Street.

Map of access to highways near Chicago's Old Town neighborhood

There it is, guys – your ultimate guide to Chicago'due south Erstwhile Town. If you're non already living in Old Town, peradventure y'all're gear up to phone call it home now. Helping folks notice apartments in Chicago's best neighborhoods is what we do best, we love doing it, and we're fix to help!

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Source: https://www.hotspotrentals.com/the-ultimate-guide-to-chicagos-old-town-neighborhood/

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