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 city on the planet. From South Loop to West Loop, Lakeshore East to Lincoln Park; each fits just right and plays its own unique role.  

But, I gotta say, Old Town is a standout piece of the Chicago neighborhood puzzle. Forget a rebirth – this historic neighborhood was hipster before hipster was a thing. 

Hello, Old Town 

Old Town takes its neighborhood status so seriously, you can actually feel the neighborhood-iness in the air. Simply take a stroll down its tree-lined sidewalks and you’ll get a sense of the community that’s so often lost in urban neighborhoods. 

And I’m telling you, this location cannot be beat. Old Town sits less than two miles north of the heart of downtown Chicago and just a mile west of the lake. Its neighborhood neighbors (yup, that’s a thing) include Gold Coast to the east and Lincoln Park to the north. Pretty good company, right? 

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

The neighborhood comprises sixty-four acres–its original and modern borders split by North Avenue–running straight through the center. The part of the neighborhood known as the Old Town Triangle–as it has been known since the 1950’s–takes its throne atop this jewel of a ‘hood. 

Now, locals may say – “whoa, wait…half of that is Lincoln Park.” And you know what? They’re right. Depending on who you ask, a good chunk of Old Town that lies north of North Avenue is also considered Lincoln Park. It’s cool, we’re all friends here! 

Old Town is a pretty small area, even using Google’s generous borders, measuring one mile north to south and just shy of a mile east to west. Run the perimeter and you’ll have a 5k under your belt. 

Old Town History

The Cabbage Patch 

Think history lessons are boring? Not this one. First, imagine this bustling urban neighborhood as 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 first developed the area and even before Old Town was even inside Chicago’s city limits. 

It was those German settlers who built one of the neighborhood’s greatest treasures – St. Michael’s Church. 

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

A New Old Town

The rest of Chicago took the clean slate as an opportunity to create a logical grid of perfectly straight streets running east, west, north and south. I’d like to personally thank these visionary city planners for creating a street system that makes it near impossible for even its most geographically-handicapped residents to get lost (that’s me!). 

But – Old Town was an exception. Post-fire, the Triangle kept its original willy-nilly street layout. These winding streets, full of narrow one-ways and asymmetrical intersections, still exist 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 apartment buildings. Gothic windows, Victorian spires, insanely-ornate balusters and spindles, swooping roofs…the list goes on and on.

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

The Triangle Comes Together

The Great Depression was hard on Old 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 it shine once again. They banded together and formed the Old Town Triangle Association; a super-active community organization that’s headquartered in the Triangle to this day. 

One of the first projects the Association undertook was to hold a small Art Fair. They figured the artisans in the neighborhood could sell their art and the community would open its doors to invite visitors to discover their hidden gem of a neighborhood. And thus, the face of Old Town changed forever. 

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

North Wells Revolution

Up until the 1960s, the Triangle truly was Old 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 down the street today, you can still get a sense that this place has a story to tell. And it 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 two decades, iconic restaurants, music joints and just-plain weird attractions opened their doors up and down Wells. Ask anyone familiar with Old Town of the 1960s and 70s and they’re sure to reminisce about noshing on free pickles at The Pickle Barrel and wandering through the Royal London Wax Museum. If they were lucky, perhaps they caught music icons like Steve Goodman and John Prine jam at The Earl of Old Town Cafe & Pub. 

Unique shops peppered the street as well. Stores hawking candles, jewelry, records and even peace pipes. You can practically smell the patchouli in the air, right? The first 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 Old Town Triangle Association is more active than ever. Because of this, the neighborhood has been able to keep its charm and unique characteristics while still embracing inevitable change and development. 

Today you’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. 

And, Old Town’s residents know just how fortunate they are. They get charm on their doorstep and everything the city has to offer is just a hop, skip and a jump away. Old Town 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’s practically priceless, but what’s it like to live there? 

The area to the south of North Avenue, on either side of Wells Street, is always humming. On the south edge you’ll find luxury high-rise apartments and everyday conveniences. When your dentist, grocery market and drug store are all within walking distance, life is just easier. 

But this south-of-the-north-border section of Old Town is charismatic too. Zip up Wells Street a couple blocks and you’ll be greeted by the iron Old Town gates. 

Block by block, modern amenities of the city fade and the Old Town of yesteryear emerges. N. 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 Avenue, and you’re officially in the historic Old Town Triangle. Detour off Wells to discover a treasure trove of historic homes and buildings. Call me a nerd, but this is one of my favorite things about Old Town. I’ve spent entire afternoons drifting up and down streets, oogling gorgeous front doors and wrought iron balconies. 

Small Business Central 

This ‘hood is all about small business and home to independent coffee shops, pastry shops, cafes and more. Treat yourself to local favorite Cocoa + Co. You should skip the coffee and go straight for a dark hot chocolate (holy yum). Just a couple blocks southeast of there, you’ll find PiniPico Brazilian Café, a family-owned shop where you can enjoy authentic Brazilian coffee and pastries.

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 single-handedly responsible for me finally taking up cooking. With thousands of spices and blends packed into the cutest little shop, I could spend hours peppering the staff with questions.

Conveniences

Yes, I love those independent shops and boutiques but if there’s one thing I cannot live without it’s Target. Fear not, bullseye lovers, there is a Target just a squeak outside the official boundaries of Old Town in the southwest corner on Division Street. 

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

• Mariano’s: full-service grocery on Clybourn Avenue
• Jewel Osco: full-service grocery between Clybourn and Sedgewick
• Aldi: discount grocery at Division and Wells

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

Old Town Rental Properties 

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

North+Vine

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

Old Town Park

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

1325 N Wells

Life is a little more fun when you live right on Wells. This contemporary midrise, which opened in 2019, lends luxury living smack dab in the center of Old Town. You’ll love the location, its pet-friendly policies and rooftop lounge pool. 

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

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

Best Restaurants in Old Town 

The restaurant 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 will not let you go hungry, or thirsty. 

Best Italian: Topo Gigio

Located on Wells Street, this award-winning Italian restaurant is the real deal. The authentic ambience, charismatic staff and homemade pasta will have you coming back again and again.

Best Quick Bite: Small Chevel

That “best burger” – it’s here! Don’t let the term “quick bite” fool you – you’re gonna savor every last bite at Small Cheval. This quick service version of West Loop’s Au Cheval, 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. 

Best Brunch: Benchmark

This ain’t no dainty breakfast, but a “last night was too much fun and we need to recover” kind of brunch joint. In fact, at night, Benchmark is a bar-meets-dance club but come daylight, it serves up the craziest bunch buffet. I’m talking about 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 treat on a Sunday morning. 

Best Dessert: Jeni’s Splendid Ice Cream & La Fournette

Choosing between Ice cream and pastries? No thank you. We have a tie here, folks. 

First up – Jeni’s Splendid Ice Cream on North Wells. This Ohio-based artisan ice cream shop has eight Chicago locations (and growing!) and Old Town is lucky to call one theirs. Prepare yourself to wait in a line out the door anytime the temperature is above 50 (hey, we’re Chicagoans). But, it’s worth it. Insider pick: the goat cheese with red cherries in a sugar cone. 

Next – La Fournette. Oui, oui, oui! I would pay for the smells alone at this French bakery. With authentic roots (the French owner is a World Baking Champion) and pastries that literally melt in your mouth, La Fournette is a Wells Street jewel. Locals return again and again for  the almond croissant, but I’m a sucker for their macarons. 

Old Town Bars and Nightlife

Cold beers to craft cocktails – Old Town’s got you covered.

Best Dive Bar: Old Town Ale House 

This iconic bar has been in Old Town since 1958, and it shows. Anthony Bourdain called it the best dive bar in Chicago, and he’s right. This bar has not kept up with the Old Town gentrification, which is all the more reason to love 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 House is cash-only.

Best Wine: Glunz Tavern

Located near Division and Wells, the Glunz Tavern is part specialty liquor store (House of Glunz), part 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 wine because it just feels so Old Town. It’s no surprise since the tavern-style bar was actually restored by the granddaughter and great-grandson of Louis Glunz (the original owner) descendants in 2012. 

Arts and Entertainment

Art Festivals 

Old Town’s heritage is ripe with art and entertainment – from the first art fair to the mid-century music scene to the opening of the famous Second 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 70 years now! The event, organized by the Old Town Triangle Association, is held the second weekend of June each year up in the Triangle. The art fair has come a long way from its humble beginnings with crowds flocking from near and far to attend one of the best art shows in the country. 

Over 250 juried artists are invited to participate each year and it’s estimated over 30,000 visitors attend. And, it’s more than art that draws attendees. I’m 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 home stalker. 

There’s live music too – jazz and folk, naturally. And the food…oh my. Come hungry, and thirsty! 

Wells Art Festival 

Wait a minute…another art fair?! Yes! The Wells Street Art Festival is held the same weekend as the Old Town Art Fair (second weekend in June) and takes place on N. Wells Street between North and Division. 

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

The atmosphere is more rock and roll, with live music lasting into the evening hours. 

Comedy Central 

Just when you thought Old Town couldn’t get more colorful, it does, with this unexpected legacy: Comedy! It’s comedic history dates back to the 1950s and the laughs just keep coming. 

The Second City

If you know Chicago, you know The Second City. The iconic venue opened in 1959 and with it, brought a comedy culture – and comedy superstars – to Old Town. It’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 Second City has gotta be on your bucket list. 

The Second City isn’t the only comedy player in the neighborhood. Zanie’s has headline comedians on stage 7 days a week. Up Comedy Club, owned by The Second City, has a rotating show line-up ranging from improv to stand-up to fall-down-funny skits. 

Old Town Demographics 

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

• Population: 39,019
• Median Age of Population: 33.6
• Total Households: 23,269
• Average people per Household: 2
• Households with children: 10.5% 
• Owner-Occupied: 39.8%
• Renter-Occupied: 60.2% 
• 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. But, that doesn’t mean its residents don’t get out and enjoy the outdoors. Take one lap around any block in Old Town and you’ll see at least three French bulldogs (okay, I kid…kinda). So yes, Old Town is super dog-friendly and appeals to their humans who prefer the outside to the inside too. 

Old Town Residents have access to tons of parks that aren’t IN Old Town, but so close, you can call them your own. 

• Seward Park – just blocks from the newer luxury apartment along Division Street, this 7-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 Old Town Triangle. The chess tables are quaint, but it’s the bronze statue of Hansel and Gretel, which honors the Triangle’s German settlers that adds real charm to this little corner of the neighborhood. 

• Bauler Playlot Park – a kid-friendly park, with a play structure, just north of the Triangle in Lincoln Park. 

• Sedgwick Park – tucked between historic brick apartment buildings, this little park is located in the Old Town Triangle. It has a small play structure and in classic Old Town fashion, an art installation featuring two lifesize modern metal horses. 

• Lincoln Park – this massive, 1,100+ acre park lies just on the east side of N. Clark. A big bonus for families – Lincoln Park Zoo is just a 15 minute walk from the center of the Old Town (maybe 20 minutes if you’re pulling a wagon). 

• North Avenue Beach – if you love to spend summer with sand between your toes, the lakeshore is just one mile away. 

Neighborhood and Business Associations

There are two active neighborhood associations in Old Town: 

• Old Town Triangle Association – an engaged community of neighbors, this historic association is focused on preserving Old Town’s historic district, neighborhood improvements, capital improvement, the Old Town Art Fair and other fun events that bring the community together. 

• Old Town Merchants & Residents Association – residents and business owners team together to keep Old Town “safe and vibrant.” The group’s main focus is on the area in and around N. Wells, but any Old Town resident or business can join.

Schools (K-12) 

• Franklin Fine Art Center – this K-8 public school is Chicago’s only citywide magnet school for the arts. A small student population (under 400 pupils) and a focus on drama, dance, music and visual arts make this unique public school an excellent and convenient option for Old Town residents. 

• Manierre Public Elementary School – a PreK-8 public school with an emphasis on “College, Careers and Civics”. The attendance boundary covers the part of Old Town south of North Avenue. 

• LaSalle Language Academy – located in the Old Town Triangle, this K-8 public magnet school focuses on culture and language. 

• Catherine Cook School – a private, Pre-K-8 school located just off N. Wells on Schiller Street. This community-centered school  “empowers students from preschool through eighth grade to be adaptive, confident and productive stewards of an evolving world.”

• Immaculate Conception St. Joseph School – this private, Catholic parish school is located in the middle of Old Town, just a block off N. Wells on N. Park Avenue. It has two campuses and 450 students in grades preK-8. 

Parking

I’m not gonna sugarcoat it, parking in Old Town is a less than joyful experience. Between the congestion and narrow streets, it’s not easy. The key to headache-free parking is to be prepared. Sure, you might snag coveted street parking (a meter will run you $4.50 an hour) but 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 Old Town, Chicago’s public transit options make it easy. 

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 Old Town at the North/Clybourn Station. 

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

Highway Access

Old Town is tucked into the city, but it’s easy enough to find your way to major highways. US-41 (Lakeshore Drive) is a couple-minute drive east. The easiest way to hop on is to take North Avenue to N. LaSalle Drive. 

Access to I-90 is 2.5 miles west along Division Street.

There it is, guys – your ultimate guide to Chicago’s Old Town. If you’re not already living in Old Town, perhaps you’re ready to call it home now. Helping folks find apartments in Chicago’s best neighborhoods is what we do best, we love doing it, and we’re ready to help!