Things to Do in Old Town

The best things to do in Old Town include comedy clubs like Second City and Zanies, the Chicago History Museum, and a legendary dive bar.

Old Town is a residential neighborhood with lots of bars and restaurants. The neighborhood has lots of gastropubs but lacks formal dining. Wells Street is the center of activity in this neighborhood.

Last updated: March 2022

Read More About Old Town:
Restaurants in Old Town

Where is Old Town:

Old Town is located between the Gold Coast, River North, and Lincoln Park.

How to Get to Old Town:

The easiest way to get to Old Town is to take the Brown Line train to the Sedgwick stop. Or, North Avenue and Division Street both have buses.

Things to Do in Old Town:

Parks and Outdoor Activities:

North Ave Beach

Did you know that Chicago has 28 miles of beach along Lake Michigan? North Avenue Beach is located right off of North Avenue (a pedestrian tunnel that goes under Lake Shore Drive will take you there). This is a big hub of activity in the summer. There are volleyball courts, plus paddle boards, kayaks, and bikes for rent. Volleyball leagues are very popular in Chicago and lots of people play after work in the summer. North Avenue Beach also has a path for jogging and biking.

Bike the Lakefront Path

Biking the Lakefront Path is a fun activity and a great means of transportation if you want to explore neighborhoods to the north. If you don’t have your own bike, Chicago as a bike share system called Divvy, and you can rent a Divvy bike and then bike along the path. 

Green City Market

Yes, this is actually in Lincoln Park, not Old Town, but it is so close to Old Town that we wanted to include it. The market takes place outside on Wednesdays and Saturdays from May to October and has a wide variety of vendors. You can pick up fresh produce and flowers, buy freshly baked pastries, or have lunch.

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Museums:

Chicago History Museum

This museum focuses on sharing the history of Chicago. See dioramas that depict what the city looked like before the Chicago Fire and browse special exhibits that cover topics like fashion, famous Chicagoans, and Chicago history. 

Immersive Van Gogh

A massively popular special exhibition at LightHouse AirSpace that involves music and projections of Van Gogh’s paintings.

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Theaters:

A Red Orchid Theatre

An edgy theatre company that performs in an intimate 75-seat space. Often they host world premieres and Chicago premieres of new plays.

Comedy Clubs:

Second City

One of the most iconic comedy clubs in America is right in Old Town! So many SNL cast members are Second City alums, and seeing a show is a must when you are in Chicago. The club has multiple stages with different shows, so check their websites for listings and pick what interests you! The shows at Second City usually feature an ensemble cast and are focused on improv – meaning each show is unique. 

CSZ Chicago

ComedySportz improv group that is now performing at Piper’s Alley (the same building as Second City). Their signature show is a 90 minute interactive show where two teams complete for laughs. 

Zanies

People go to Second City to see improv and they go to Zanies to see stand up. Lots of touring comedians (you will recognize some names of SNL cast members) make stops at this comedy club.

Shopping in Old Town:

The Spice House

A beautiful shop that specializes in spices. You can find unique and hard to find spices here along with your basic staples.

Judy Maxwell Home

A quirky urban general store on Wells Street where you can find pool floats, home decor items, books, games, and more. It’s a fun place to shop for gifts.

Sara Jane

Sara Jane stocks contemporary women’s clothing and accessories.

String a Strand on Wells

A jewelry and bead store where customers can design their own jewelry.

Nightlife:

Old Town’s Wells Street is one of Chicago’s busiest centers for nightlife. The street is lined with bars and on weekends often there are people lined up outside waiting to get in. Sometimes bachelor and bachelorette parties are dropped off by the busload. In the evenings, you can find groups enjoying happy hour outside. This area is always lively. If you want to avoid the partiers, visit a dive bar like Old Town Ale House or Marge’s Still.

Old Town Ale House

Roger Ebert called it “the best bar in the world that I know about.” It is Chicago’s most famous dive bar, and a favorite of the late Anthony Bourdain. Old Town Ale House is a cash-only no-frills bar. The vibe here is a bit different since Old Town Ale House is not on Wells Street and it attracts patrons of all ages. Visiting this bar is one of the best things to do in Old Town.

Marge’s Still

Another dive bar, Marge’s Still is a low-key bar/restaurant and it is one of the longest running taverns in Chicago with a history dating back to 1885. During the Prohibition, a secret staircase led to a bar serving bathtub gin. Today Marge’s Still is a bar/restaurant and a locals’ hangout. They serve classic American bar food and the bar is a nice place to hang out away from the Wells Street crowds.

Woodies Flat

One of the more low key Wells Street bars, Woodies has solid pub grub and hosts events like trivia night.

The Vig

Definitely a good choice for happy hour, especially if there is space on the sidewalk patio. There is a nice menu of sharable snacks like spreads and dips too. On the weekends this is a singles scene and sometimes they have live music.

Happy Camper

A pizzeria/bar with a large sidewalk patio and plenty of televisions for watching sports. This is a popular happy hour spot that can get a little rowdy at night.

Benchmark

Benchmark is a sports bar by day and a bar/club hybrid at night. It’s popular, especially with big groups (birthdays, bachelor and bachelorette parties, etc.) so don’t be surprised if there is a line to get in on the weekends.

80 Proof

The space has three levels with a different DJ on each level and is basically a nightclub.

Utopian Tailgate

The tailgating themed bar located on a rooftop above Second City where twenty-somethings chug white claw. 

Annual Events in Old Town:

Old Town Art Fair and the Wells Street Art Fair

It is easy to get these two festivals confused, or to think that they are the same event since the take place at the same time on nearby streets in Old Town. The Art Fair is focused on art and the Art Festival is a street festival with bands and more food and drink options.

Air and Water Show

This annual event that takes place in mid-August attracts a massive crowd. Locals have parties on their rooftops while others gather on North Avenue Beach to watch.