Old Town/Near North

Neighborhood guide to Old Town and Near North on the North Side of Chicago.

UPchicago Bar Crawl: Old Town

UPchicago Bar Crawl: Old Town

We are on a mission to perfect the art of the neighborhood bar crawl… and I’m not gonna lie, I think we may have accomplished our goal with this one. Good beer, good pub food, so-bad-it’s-good karaoke, and one member mysteriously disappearing mid-crawl? Yep, we’ve officially done it.

Old Town Ale House (Bar, Old Town)

Do like we did and post up at a table with some good friends, good beer, and watch as the graphic wall art turns funnier with each drink you put down.

Wells on Wells (Bar, Old Town)

Wells on Wells is a fairly low-key bar, with two flat screens, plenty of tables and a proudly displayed Iowa Hawkeyes flag.

Declan’s Irish Pub (Bar, Old Town)

Born in ’72, Declan’s Irish pub is a great place to catch some Oklahoma football or have a quiet weeknight beer.

Burton Place (Bar, Old Town)

This small 4am dive bar is the perfect way to end an evening in Old Town.

Old Town Pub (Bar, Old Town)

The underground lairish style of Old Town Pub feels classic, the wooden walls are welcoming and unpretentious.

Zanies Comedy Club

Zanies Comedy Club

Zanies Comedy Club has been host to comedians such as Chelsea Handler and Jerry Seinfeld, and is the king of Chicago stand-up comedy.

Flat Top Grill (Restaurant, Multiple Locations)

At Flat Top Grill, you are the head chef.

Corcoran’s Grill & Pub (Bar, Old Town)

Nestled on the bustling corner of North and Wells, Corcoran’s offers an oft-tried, rarely accomplished juxtaposition of the traditional Irish pub and the Chicago neighborhood bar.

Second City Comedy: 50 Years of Funny

For the past fifty years, Second City Comedy Troupe and school, whose main focus is improv-based sketch comedy routines, has been grooming some of the funniest comedians of our time.

Old Town School of Folk Music

Don’t get distracted by its name, this Chicago music school offers everything from concerts to instrument instruction to a program introducing music to pre-schoolers.

Old Town Ale House (Bar, Old Town)

Angels & Kings (Bar, Near North)

Pizano’s (Restaurant, Near North/Gold Coast/Loop)

There are endless options when it comes to pizza in Chicago. If you’re looking for a traditional pizzeria with good food, a fun atmosphere, and a little bit of history, Pizano’s is a great choice.