May 20, 2025

Old Town Ale House Chicago

Famed dive with historic roots

"" Old Town Ale House" is one of my favorite spots to enmesh myself in the history, art, and unique company found in Chicago."

Walking down the bustling streets of Old Town, you're likely to pass their ratty, algae-green awning without a second glance—choose to take a peak and stop inside this dive bar, though, and you’ll be taking a seat among some of Chicago’s richest, most historic spots in the city.

Spend enough time there and you’ll become part of the walls… literally. One of the bar’s most notable features is the portraits of historic bar dwellers hanging throughout almost every inch of the interior. Located directly across the street from Second City, it’s no surprise that some of comedy’s most famed faces reign high above on the walls, including Tina Fey and Michael Shannon. These odes to Second City greats aren’t the only comedic references amongst the paintings—peruse around and you’ll see a naked Sarah Palin strapped with a rifle, international leaders in compromising positions, and a whole lot more.

My advice to first-timers? Grab a seat at the bar, order the negroni on ice, queue up an instrumental melody on the cash-only jukebox, settle in, and buckle up for a visual ride through the bar’s eclectic, famed story.

Whether you stop by for the notoriety or spend an entire day pleading your case to get your portrait painted, Old Town Ale House is one of my favorite spots to enmesh myself in the history, art, and unique company found in Chicago.

028-beach-bar-1
Bars

About this spot

219 West North Avenue

USD

no-price

3129447020

Find your way with 116 Insider Tips from our Local Spotters

Discover hidden gems and all our locals’ favourites! Get full access to our Chicago guide.

Nice place right!? There’s so much more to discover:

Discover all other hidden gems in Chicago

Superdawg Drive-in

Classic Chicago hot dog spot

Founded in 1948, "Superdawg" is THE quintessential Chicago hot dog place - they'll bring your order right to your car, like they did in the '50s!

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Jul 2, 2025

Denden Restaurant

Affordable Eritrean

The lentils are filling and creamy; the veggies are lightly cooked and nourishing; the injera bread is the perfect balance of slightly tangy and spongey.

021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Jul 1, 2025

OMI Cafe

Japanese Dessert Café

OMI has many good menu options, but their Japanese dessert toast is their all-star. Think of it as a fluffy French toast served with vanilla ice cream.

020-coffee-cup-1
Coffee & tea
024-burger-1
Snacks

by

Lydia

Schultz

Jul 1, 2025

Sweet Rabbit Bakery

Loaf Perfection

Choose from multigrain sourdough, their house sourdough and miso rye sourdough; pastry choices include croissants, morning buns, and fruit danishes.

020-coffee-cup-1
Coffee & tea
024-burger-1
Snacks

by

Lydia

Schultz

Jul 1, 2025

The Momo World

Nepalese Dumplings

Momos are bite-sized dumplings from Nepal and Tibet, usually filled with meat that is seasoned with spices like turmeric, garlic, cumin, and chili peppers.

021-spoon-and-fork-1
Restaurants
024-burger-1
Snacks

by

Lydia

Schultz

Jul 1, 2025

Publican Quality Bread

Bread at its Finest

Their bread that has the perfect ratio of chewy on the inside and crispy on the outside. The 1979 multigrain sourdough is some of the best bread I've had!

020-coffee-cup-1
Coffee & tea
024-burger-1
Snacks

by

Lydia

Schultz

Jul 1, 2025

Gundis Kurdish Kitchen

Chicago Kurdish

They are arguably most known for their "Kurdish breakfast" an elaborate spread of cheese, jams, fried cheese, olives, fries, cucumbers, tomatoes and bread.

020-coffee-cup-1
Coffee & tea
021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Jul 1, 2025

Taco Loco of Pilsen

Juicy Street Tacos

The tent is run by Adan, who mans the booth entirely alone. His ingredients are kept fresh in coolers which are grilled on the spot in front of customers.

024-burger-1
Snacks

by

Lydia

Schultz

Jul 1, 2025

La Fournette

French Family Bakery

There are many pastry options like croissants, an assortment of macaron flavors, fruit danishes, quiches... My favorites are the fruit-stuffed beignets!

020-coffee-cup-1
Coffee & tea
024-burger-1
Snacks

by

Lydia

Schultz

Jul 1, 2025

Hendrickx Belgian Bread

Expert Croissants

While most croissants are buttery and flakey, the ones at Hendrickx are denser and chewier. In my opinion, this makes them even better.

024-burger-1
Snacks

by

Lydia

Schultz

Jul 1, 2025

BULSHO Restaurant

Spicy Somalian Food

BULSHO serves a traditional Somalian breakfast that is comprised of seasoned meat or veggie stew served with anjero - a fermented flatbread.

020-coffee-cup-1
Coffee & tea
021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Jul 1, 2025

Gorée Cuisine

Senegalese Comfort Food

Start with a freshly steeped cup of sweet mint tea, a staple of any Senegalese meal. Then order fataya, triangular fried pastries with a savory filling.

021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Jul 1, 2025

Heading to Chicago?

116 Insider Tips from our local Spotters

Authentic Stories by Real People

Escape the Crowd & Travel Slow 🐌

... for just €9.99

Heading to Chicago?

0 Insider Tips from our local Spotters

116 Insider Tips

✓ Escape the Crowds

✓ Find Spots nearby

✓ Authentic Stories

... for just €9.99

App Download Download our app

City guides by those who know the city in and out!

Our Locals' Favorite Bars

Our team loves Chicago

Get to know our other Spotters from Chicago

As featured on:

New-York-Times
the-guardian
mashable
the-sunday-times
false
0
false
71
Filters