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What to do in Old Town Chicago

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A guide of what to do in Chicago’s Old Town – the neighborhood I have lived in for the past six years! Old Town is just two train stops north of downtown/the loop yet it has a neighborhood feel.

A guide of what to do in Chicago’s Old Town! This neighborhood is just two train stops north of downtown/the loop yet it has a neighborhood feel.

During the day you will see locals dining at the many restaurants along Wells Street, heading to the beach, and go to one of the many fitness classes in the neighborhood. At night, the neighborhood is a bit different. Wells Street has become a big hub of nightlife in Chicago. On weekends there might be lines outside some of the bars. 

Getting to Old Town Chicago

The easiest way to get to Old Town is to take the brown line train to the Sedgwick Stop. 

Where to Stay in Old Town

Lincoln Hotel

If you are looking for a hotel in Old Town, this is it! As in, there aren’t really any other options. Luckily, this hotel is great. You could argue that it is in Lincoln Park, the line between the two neighborhoods isn’t strictly defined. Stay here because it’s right across from Lincoln Park – and the area where the Green City Farmers Market takes place on Wednesdays and Saturdays.


Since there aren’t many hotels in the neighborhood, you might want to check out airbnb for more options.

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What to do in Old Town Chicago

What to do in Old Town Chicago

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. I try to go once a year. 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. 

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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. 

Chicago History Museum

I love this museum that 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 famous Chicagoans and Chicago history. 

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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

This is one of my favorite warm weather activities! Chicago as a bike share system called Divvy, and you can rent a Divvy bike and then bike along the path. 

Chicago’s Green City Farmer’s Market

Green City Market

Yes, this is actually in Lincoln Park, not Old Town, but it is so close to Old Town that I 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.

Annual Events

Old Town Art Fair and the Wells Street Art Festival

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This pair of festivals take place the first weekend of June. The Old Town Air Fair is a large art fair that takes place in the historic Old Town Triangle. The Wells Street Art Festival is a rowdier event with a music line up and it turns into a street party at night.  

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.

Where to Eat in Old Town Chicago

There are a lot of restaurants in Old Town, but there are not a lot of good restaurants in Old Town. Here are my recommendations:


A classic diner and one of our go-to spots for Sunday brunch. The food is consistently good and the menu is big enough that we can always find something new if we want to.

Twin Anchors

A little barbecue spot hidden away on Sedgwick Street just north of North Avenue. It gained fame when Frank Sinatra used to hang out here, and more recently when a scene from The Dark Knight was filmed here. The restaurant is known for their ribs and for sometimes having a long wait for a table since they don’t accept reservations.

Happy Camper

Happy Camper is half pizza place and half bar. If you go at night, I would say it’s 80% bar and no so much about eating. It’s fun, the food is pretty good, but the wait for a table can be extremely long since people often stay for hours to watch football, basketball, and baseball games on the many large tvs throughout the space.


I firmly believe that this is one of the best places to eat in Old Town. They serve both sushi and cooked meat and noodle dishes, and their bento box weekday lunch special is excellent! It has a calmer and quieter atmosphere than many of the other places to eat on Well Street.

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La Fournette  

An authentic French bakery right in Old Town. We love to stop in to get pastries and bread to go, but they also have small breakfast and lunch menu with options like quiches, sandwiches, salads, crepes, and soups. Go here because this is exactly the type of business that I want to see thrive in my neighborhood.

Real Good Juice Co

A juice bar that serves cold pressed juices and smoothies. I love the Wendy Peffercorn, a smoothie with mango, strawberry, camu camu, lemonade, and mint. It isn’t on the menu anymore but they can still make it. And we swear by taking the ginger shots when we feel a cold coming on.

Cocoa + Co  

A shop/café devoted to all things chocolate! You can try one of the hot chocolates, enjoy pastries and chocolates, or shop from the huge selection of chocolate bars. Food Network says it’s one of the best spots for hot chocolate in the country!

Kanela Breakfast Club

Kanela Breakfast Club

This breakfast/brunch/lunch spot has a few locations in Chicago, and it’s a staple for a reason: the food is good and the menu has plenty of options. I love the goat cheese omelet, the benedicts, and if I want lunch I get the grilled cheese. It can be busy on weekends, so we try to go before 10am. Sometimes I go there for weekday lunch when I want to get away from my desk.

Bombo Bar  

Don’t let the name confuse you. This isn’t a bar. It’s a quick service spot for burgers, doughnuts, gelato, and elaborate hot chocolate.

Small Cheval

An offshoot of the wildly popular Au Cheval in the West Loop, this quick service restaurant serves up their famed burgers, fries, and shakes. (This photo is of the nearly identical burger at Au Cheval).

Where to Shop in Old Town

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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.

Chicago Spotlight: Plum Market

Plum Market

Sure, it’s a grocery store. But it’s my favorite grocery store. This upscale market has an excellent butcher, a very delicious buffet, an incredible cheese selection, and a coffee shop. 

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This how millennials have reinvented the bodega. It’s part café and part convenience store that specializes in grocery items, alcohol, and household essentials. The brand got its start as a delivery service and you can use their app to get items delivered to your home – this is how I get my beer and wine delivered. 

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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. The selection is really excellent and it’s a shop that I love having so close to home.


If you were to list the top areas for nightlife in Chicago, Wrigleyville in Lakeview, Hubbard Street in River North, and Well’s Street in Old Town would be at the top of the list. Wells Street can be busy, rowdy, crowded, and loud. It’s the place where bachelorette and bachelor parties get dropped off by the busload. It isn’t really the place were you can have a quiet cocktail with a date. I just want to set some expectations. 

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The Vig

Definitely a good choice for happy hour, and the food is good! We like to come here for drinks and apps after work in the summer since we can sit outside on the patio. On the weekends this is a singles scene and sometimes they have live music.

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.

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

This is our go-to bar. The food is good, they have trivia and a burger special on Mondays, and it isn’t as wild as some of the other Wells Street bars.

Old Town Pour House

Not to be confused with Old Town Ale House, Old Town Pour House is a large bar/restaurant on Wells Street. It is a bit more food focused.

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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

Originally opened as Steak Bar and then rebranded as 80 Proof, the space has three levels with a different DJ on each level and is basically a nightclub. According to Yelp it seems that people go here to a brunch buffet with bottomless mimosas. 

Utopian Tailgate

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

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